Oregon Obsessed

How to Plan an Incredible Oregon Road Trip (14 Days)

Looking to plan an amazing road trip in Oregon? You’re in the right place. We live in Portland, and spend a big chunk of our summers on the road exploring our adopted home state of Oregon. We’re here to use our experiences around Oregon to help you plan your own amazing Oregon adventure. 

We’re going to go over a perfect road trip itinerary that takes you to many of our favorite places in Oregon over 14 days, which is based on our own experiences exploring the state. 

Have more or less time than that? Have no fear, we’ve got ideas on how to structure a trip with more and less time below the main itinerary, and you can use the details in the main itinerary to help you plan out your trip. 

We were lucky enough to spend two whole months on a road trip around Oregon a few summers ago after we had to scrap our international travel plans, and it taught us an important lesson: you don’t need to fly halfway around the world to find wild and beautiful places – sometimes they’re right in your backyard the whole time . 

It also cemented our belief that Oregon was the place we wanted to put down roots and create a home base after years of living on the road. 

Fast forward a couple of years, and we decided to make our forever home in Portland, Oregon, and that initial time exploring Oregon was a huge part of why we ultimately ended up making that decision.

Oregon has it all – the coast, the mountains, the desert, a truly unbelievable number of amazing waterfalls, and more. 

In this complete guide to planning your Oregon itinerary, we’re going to give you the logistics you need to know – when to visit and our recommended route – along with a mini guide to each place on the itinerary. 

That mini guide will have information like what to do and where to stay – all based on our own experiences exploring Oregon – along with links to more in-depth content we’ve written on the destination. 

In each “where to stay” section, we’ll give you options for camping (which is what we usually do) and not camping, which we recognize is what the vast majority of people prefer. 

Finally, at the end, we’ll give you some ideas on how to shorten or lengthen the itinerary to fit your particular trip. 

Sound good to you? This guide is super detailed, full of our tips and favorite places based on our extensive experience exploring Oregon, which means it’s LONG. Strap yourself in, grab a cup of coffee (or beer or wine, no judgment here), and let’s get to exploring Oregon!

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Disclaimer: Some of the links in this post, like hotel and vacation rental links, are affiliate links, meaning at no additional cost to you we make a little bit of money if you click through and book. That being said, we would absolutely never recommend something to you that we don’t stand behind 100%.

A Quick (and Oversimplified) Oregon Geography Lesson

Before we get into the road trip itinerary, let’s quickly talk about Oregon’s geography, and what it means for your trip. 

First of all, Oregon is a lot bigger than you probably think. It’s the 9th largest state in the country by square mileage, which is a fact that blew my mind. Driving between places can take several hours, if not more. 

Why do we bring this up? Because it has one major implication for your trip.

Unless you want to spend full days of your trip driving without stopping to see the scenery, you’re not going to be able to see the entire state .  

Fear not – we have a strong perspective on where you should focus your time if it’s your first trip to Oregon. Which means we need to talk about Oregon’s geography. 

Oregon is a very diverse state when it comes to landscapes, which is part of why we love it. It’s home to rocky coastline, wide sandy beaches, rolling hills and lush valleys, moist rainforests, towering snowy peaks, and even the high desert. 

When you think about Oregon’s geography, we’d cut the state roughly into quadrants, with Eugene as the center point in the state.

If it’s your first time in Oregon, you’re going to want to focus on the northwest quadrant, almost exclusively . The exception might be Crater Lake National Park, which we have a whole section on below to help you figure out where to fit it in. 

If you start to try fitting in places all over the state, you’re going to spend entire days driving long distances, which we don’t really think is the best experience.

For reference, it takes three and a half hours to go from Newport on the Oregon Coast over to Bend (without traffic). Then, it’s another two hours to the Painted Hills from Bend. And a full four hours back to Portland from there. 

In this itinerary, Bend is the furthest east you’ll go. It’s just not feasible to get to every corner of the state, especially with limited time. 

If you happen to have an extra week (lucky you!), that’s when we’d add the Painted Hills and Wallowa Mountains, and some of the other spots in eastern Oregon. Or the southern Oregon coast, which is much more rugged and wild than the northern coast that you’ll cover in this itinerary. 

How Many Days Do You Need for this Road Trip?

We really, really think that to do a full road trip around Oregon that includes both the northern coast and Bend, you need a full two weeks (14 days) . Otherwise, you’ll spend way too much time driving, and not enough time out exploring. 

Which is exactly how we’ve written the road trip below. 

If you have 7-10 days , we’d do a more focused road trip that follows a figure-8 with Portland at the center. Head east to the Columbia River Gorge, Hood River, and Mount Hood, then come back through Portland and head out to the Oregon Coast for a few nights, focusing on the stretch from Astoria to Tillamook. Here’s a map .

If you do have less time, we have example itineraries for 7 and 10 day road trips below the main itinerary to help you organize your time. 

The Best Time to Plan Your Trip to Oregon

This is a very, very important section in this guide, which is why it’s the first thing we’re talking about. 

If you are interested in hiking in the Cascades – specifically near Mount Hood or Bend – your trip will need to be sometime between July and mid-October . 

Otherwise, high elevation hiking trails will be covered in snow, and some roads and sections of the parks will be closed. 

The exact timing depends on the year, precipitation, and spring temperatures (among other factors), but you will be most safe with a trip in August or September . 

The best time to plan this road trip is going to be July, August, and September . That’s when roads are open, trails are largely snow-free, and you’ll be able to see everything you want to see.

During the summer and early fall, mountain passes and hiking trails are clear of snow, days are warm and sunny, the sun rises before 6:00 am and sets after 9:30 pm, and it’s an all around spectacular time to be in Oregon. 

The downside is that, in recent years, Oregon has been ravaged by forest fires during the summer, bringing a thick smoke that makes it really unhealthy and unpleasant to be outside. It’s hard to predict, but it’s something to be aware of if you’re planning a trip in the summer. 

Early fall is another great time to visit Oregon. The weather is, for the most part, still great (though it’s a little more unpredictable than summer). 

As you get into October, things start to cool off and snow can begin to show up in some of the passes through the Cascades (the McKenzie River Scenic Byway, for example), which can make travel a bit more difficult. 

Spring is gray and wet, though late spring (think Memorial Day into June) is a cool time to visit Oregon because of the blooming rhododendrons and roses. The weather isn’t going to be the best, but you’ll probably get a few nice, clear days over the course of your trip. 

In the spring, hiking trails at elevation – like around Mount Hood and Bend – are still going to be closed. If you’re into hiking, we’d definitely recommend waiting until later in the summer .  

Winter isn’t a great time to do this road trip, if we’re being totally honest. The Cascades are blanketed in snow, which means you won’t get much of a taste of the mountains in Oregon (though you can get some skiing in at Mount Bachelor!) and the mountain passes are harder to navigate, often closing for days at a time due to winter storms. 

The upside of visiting in the winter is that the waterfalls in Oregon are WILD when it’s raining.

If you’re visiting in the winter, we’d stick to the areas west of the mountains and do the Columbia River Gorge, Hood River, Silver Falls State Park, and the Oregon Coast . For what it’s worth, we’ve done the Oregon Coast multiple times in the winter, and it’s very moody (and wet). 

Here’s a map of what a winter road trip in Oregon might look like. 

Where to Start and End Your Road Trip

This one is easy – Portland! 

Portland is not really central in terms of the state – it’s up in the northwest corner – but it is central to some of Oregon’s best sights (the coast, Mount Hood, the Columbia River Gorge, etc etc) AND it’s the best airport in the state (dare we say country?). 

Unless you live somewhere in Oregon or you’re driving up from California, the answer is Portland . 

The exception is if you have 10 days in Oregon and follow our road trip itinerary below. In that scenario, we’d recommend flying into Portland, and out of Bend (Redmond Municipal Airport, RDM) to save time on driving back to Portland just to catch a flight. 

Flights out of Bend will be more expensive and involve connecting through Portland or Seattle, but it’ll save you four hours of driving. 

Where to Fly in and Out of?

The best option, with the most flights coming in and going out, is going to be our home airport – Portland International Airport (PDX) . 

Having lived in both Seattle and San Francisco, PDX is amazing when you compare it to those airports. 

It’s relatively well organized (as well organized as an airport can really be), and it’s clean, has good local food and drink options, and the security lines are never “oh no am I going to miss my flight?” long. 

There are a couple of smaller airports in Oregon that could work, but will likely be more expensive and have fewer flight options. Those would be places like Eugene (EUG) and Bend / Redmond (RDM) .

Chances are, PDX is going to be the best choice for about 99% of people. Plus, there are more rental car options! 

Do You Need to Rent a Car?

It probably goes without saying that you will need a car to do this road trip. If you’re coming from out of state, that probably means renting a car when you arrive. 

One thing we’d recommend is that you avoid having your rental car when you’re in the city of Portland .

We’ve organized the itinerary below to have Portland at the end, and we’d strongly recommend that you drop your car off at the airport when you roll into Portland, and spend your day or two in town carless. 

Another cool option would be renting a campervan for this road trip! On our six week road trip around Oregon in 2020 – the one that made us fall in love with the state and eventually move here – we lived out of our converted Honda Odyssey. 

We love the flexibility of van living, though it certainly isn’t nearly as sexy as it looks in all of those pictures on Instagram.

We have a few favorite campgrounds in Oregon that we’ll give you in the itinerary below that are a once-in-a-lifetime experience (looking at you, Trillium). 

One thing we’ve been DYING to do is rent an Escape Campervan . If you’re looking to experience the whole camping thing, but don’t want to sleep in a tent (to be clear, we’re all for tent camping), then a campervan might be for you!

Escape’s vans are all hand-painted, have full kitchens, and would be a lovely way to experience Oregon.

Escape has an office in Portland , which is where you’d pick up and drop off your van. 

The Route for This Road Trip

With that in mind, here’s a summary of the 14 day road trip we’ll cover in detail below. 

Day 1: Astoria

Day 2: cannon beach, days 3-4: tillamook & the three capes scenic route, day 5: newport, cape perpetua, & heceta head lighthouse, day 6: drive the mckenzie river scenic byway to bend, days 7-8: bend (and the cascade lakes scenic byway).

  • Day 9: Smith Rock State Park

Days 10-11: Mount Hood (Government Camp) 

Days 12-13: hood river and the columbia river gorge.

  • Day 14: Explore Portland

Here’s a map of that route. 

We think this itinerary is a good blend of scenic drives (the Oregon Coast and the McKenzie River Scenic Byway are two of our favorites), cool towns (Astoria, Hood River, and Bend), and great outdoor adventures.

Which is basically everything we love about Oregon, packed into two weeks (minus some of the further out spots that don’t make sense here). 

Like we said, you can’t fit it all into one road trip. But we’ve done our best to include the highlights in hopes that you’ll fall in love with Oregon and come back a second (and third) time to explore more. 

Of course, that’s just the base itinerary that we’d recommend. The exact route you take is going to depend on your particular interests, what time of year you’re visiting, and more factors than we can possibly take into account here. 

We have ideas for shorter and longer itineraries below the main itinerary if you have more or less time. 

We’ll do our best to give you all the information you need to plan YOUR road trip in Oregon, but if we miss something or you have more questions, leave us a comment below and we’ll do our best to either answer your question, or point you to someone who can.

Exactly How to Plan an Amazing Oregon Road Trip Itinerary

Now that we’ve covered the logistics you need to know to really plan your trip, let’s get into the itinerary itself!

There are a couple of principles that we’re going to follow as we take you through our perfect version of a road trip in Oregon. 

  • We think you should see the mountains and the coast . Both are spectacular, and part of the reason we love Oregon is that you can go from the mountains to the coast in about two hours, give or take. It’s magical.
  • Oregon is big, and you don’t want to spend the entire time driving . We’re going to try and make sure you’re only driving a maximum of four hours between destinations, which means more time exploring, less time driving.
  • There are too many places to see in one trip . Instead of trying to fit every single place into one road trip, we think you should focus so that you aren’t just rolling into a place in the late afternoon, and leaving the next morning. This, of course, means that you’re probably not going to be able to fit every single place into your itinerary. And that’s okay! You can always come back. In this itinerary, we’re focusing on the western half of the state, which is NOT to say there aren’t amazing things to see east of the Cascades. 

With those principles in mind, we’ve created this 14 day Oregon itinerary so that you can almost literally copy and paste it for your trip if that’s what you want. 

Or, you can use bits and pieces of it to cobble together your own version of the road trip. Whatever works best for you!

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Drive Time / Distance from Portland International Airport to Astoria: 2 hours / 95 miles

Where to Stay in Astoria: You want to stay centrally so you can walk to the attractions downtown. We stayed at Norblad on our last trip, and liked it (nice location, stylish rooms, comfy beds). 

Astoria is a fitting first stop on this itinerary, because in many ways, it’s where the state of Oregon as we know it today began. Lewis and Clark Historical Park, which is just south of the city center, is near the location where Lewis and Clark made camp for three months, having completed their mission to find the Pacific Ocean. 

Now, you might be thinking that Lewis and Clark, who had completed their ultimate goal after a significant chunk of time spent struggling west from St. Louis, might have been celebrating with their feet up. 

But their arrival and stay happened to be smack dab in the middle of winter – from December through February – so rather than celebrating with the long, warm days of an Oregon summer, they were treated to constant drizzle and less than eight hours of sunlight. FUN. 

Anyway, Astoria is meaningful in many ways, from the early 19th Century and Lewis and Clark’s antics, to the time when John Jacob Astor tried to make Astoria the New York City of the west (he almost had it!). 

Today, it sits at the northwestern corner of Oregon, and is home to what has to be the highest number of breweries per capita in the country (there’s four or five, and Astoria is tiny), and filming locations for some of the iconic films of the 90’s (the Goonies and Kindergarten Cop, among others). 

What to Do in Astoria

Here are some of our favorite things to do in Astoria. 

Lewis and Clark National Historical Park : Like we mentioned, Lewis and Clark National Historical Park is near the site of Fort Clatsop, which is where they set up camp for three miserable months before heading home to report back to Jefferson. There’s a model of Fort Clatsop here, a bunch of fun information on what life was like on that expedition (and some very charismatic rangers eager to share anecdotes like the one above), and a hike that connects the fort with the coast, a route that they covered many times. However, the hike isn’t really worth too much of your time – it’s 6.5 miles one way out to the coast – we’d do the first mile or so, enjoying the ferny forests of sitka spruce trees before heading back. 

The Astoria Column : The Astoria Column is perched up on the hill above town with a commanding view out over the Columbia River and the famous Astoria-Megler Bridge – that’s the green bridge crossing the river to the Washington side. The Column is an interesting piece of art, because it is wrapped in the story of Astoria. It’s hard to see the artwork when you’re standing at the base looking up at it, but there’s a digital re-creation with labels that is helpful to understand exactly what you’re viewing. You can climb to the top of the column for an even more impressive view of the river. It costs $5 to park in the lot at the Column, or you can park at the base of the hill in town (roughly here ) and hike the Cathedral Tree Trail up for free. 

Fort Stevens State Park : This is the northwest corner of Oregon, and also – fun fact – the site of the only attack on a military base in the contiguous United States since the War of 1812 (the Japanese shelled it a few times in 1942). It’s a State Park, though it was a military base through the early 20th Century. Today, the bunkers are one of the main draws here, and are particularly interesting when there are rangers and volunteers out there to tell you stories about the local history (which is usually on weekends in the summer). It’s worth driving out to the coast and hitting the wreck of the Peter Iredale , a shipwreck on a wide sandy beach, and Clatsop Spit at Lot C ( here on Google Maps) where you can walk out along the rocks on the Pacific. 

The Breweries: Two of Oregon’s best breweries are up in Astoria – Buoy Beer Co and Fort George Brewing – and are basically a must-stop for any beer aficionados who find themselves in the state’s northwest corner. They each have a taproom within walking distance of the main drag, and both have food menus and extensive taplists, with many beers you’re not going to find outside of the taproom. In addition, there are a few smaller breweries (like Fortune and Glory Cider Company – technically not a brewery, I guess). Across the street from them is Bridge & Tunnel Bottleshop & Taproom , the best beer bar in Astoria (and a good place to try multiple beers from different breweries). 

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Drive Time / Distance from Astoria to Cannon Beach: 40 minutes / 25 miles

Where to Stay in Cannon Beach: For Cannon Beach, you have two choices – on the beach (more expensive, nice experience) or a few blocks away from the beach (cheaper, less romantic). We’ve stayed at the Inn at Haystack Rock twice , which falls in the latter category and is nice enough (but probably needs a bit of a facelift in the next couple of years). 

Cannon Beach is one of the most popular day trips from Portland , because it’s a mere 90 minutes from downtown Portland. As a result, the area can feel unbearably overcrowded on summer weekends, as Portlanders (us included) flock to the coast to escape the inland heat. 

However, on a weekday or early in the morning and later in the evening, Cannon Beach is a lovely place to spend some time.

We recently went out to Cannon Beach – our first beach foray with our dog, Lupine – midweek in January, and we were basically the only people on the hiking trail in Ecola State Park. It was wet and muddy, yes, but it was so peaceful. 

The highlights in Cannon Beach are actually the state parks that border the town on the north and south end, Ecola State Park and Oswald West State Park .

Sure, Cannon Beach – the town AND the beach – is nice, and you should definitely do a sunset walk on the beach. But definitely don’t miss the nearby state parks.  

What to Do in Cannon Beach

Here are some Cannon Beach highlights that you really shouldn’t miss. 

Haystack Rock: It’s cliche, but Haystack Rock really is an impressive sight, especially if you’re not used to the towering sea stacks that you find up and down the Oregon and Washington coast. In fact, we’d argue that Haystack Rock is up near the top of the list of tourist attractions in Oregon, somewhere below Multnomah Falls and above Powell’s Books in Portland. It’s a huge sea stack, rising 235 feet out of the surf to tower over the beach and surrounding community. It’s particularly spectacular at low tide, when you get some cool reflections in the wet sand. On our first trip to Cannon Beach, we witnessed a pair of Bald Eagles raiding the resident puffin colony for their eggs! It was quite the drama, and there are rangers on the beach in the summer who talk about the puffins and the attempts to keep them alive. 

Ecola State Park: Ecola State Park was closed for years and years until very recently, when it was reopened to the public. As you drive in on the windy, tree-lined road, it’s easy to see why a couple of bad storms put the park out of commission for a couple of years. This park is one of the most popular destinations on the Oregon Coast, so it’s likely to be busy if you’re here in the summer or on a weekend. Get there early to get a parking spot in the relatively small lots! There are two things not to miss in Ecola State Park, we think. 

  • The first is Crescent Beach , which is a short hike accessed either from the main parking lot, or by walking into the park from Cannon Beach. From the main lot, which you should visit whether you do the hike or not for the views, it’s a short downhill hike that winds through the ferny forest before an aggressive descent down to the beach. The beach is best at low tide, when it’s wide and sandy and littered with driftwood and sea stacks. Basically, everything you could possibly want in a Pacific Northwest beach.
  • The second is Indian Beach . There’s a parking lot right at Indian Beach that fills up early because it’s a popular surfing destination. You can also hike out to Indian Beach from the main parking lot in the park, which is worth doing for the coastal views along the way. 

Hiking in Oswald West State Park: This is the other Oregon state park we referenced above, and it’s equally worthwhile. There are three hikes here to focus your time on. First is the hike to the top of Neahkahnie Mountain , which is an aggressive ascent up switchbacks to a viewpoint where you can see miles and miles of coastline to the south. Second is the hike out to Cape Falcon , which navigates out to the cape on the north side of Short Sand Beach, where you’ll have excellent views back towards the beach. Be aware that this hike is almost always extremely muddy. Seriously, do not underestimate the mud, even in the early summer. Third is the hike – though it’s more of a leisurely walk – out to Short Sand Beach , which is a wide sandy beach (at low tide, anyway) that is very popular with surfers. 

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Drive Time / Distance from Cannon Beach to Tillamook: 55 minutes / 40 miles

Where to Stay in Tillamook: Tillamook itself isn’t really the nicest city, but there are some nice places to stay up and down the coast from town. We stayed in one of the tiny homes at Sheltered Nook , which is just north of the city, and really liked it (full kitchens, nice outdoor seating). 

Everyone who has spent any significant amount of time in the Pacific Northwest knows Tillamook because of the cheese, ice cream, sour cream, or some other dairy product that every supermarket carries. 

And while you’re in Tillamook, you should definitely visit their factory for a tasty, educational experience. 

However, Tillamook is also home to the Three Capes Scenic Route, which is well worth a half day of your time to explore as well. 

What to Do Around Tillamook

Here are three things not to miss when you’re in Tillamook. 

The Three Capes Scenic Route: Like we mentioned above, this is probably the premier thing to do near Tillamook. The Three Capes Scenic Route covers a 30 mile stretch of the Oregon Coast from Cape Meares to Cape Kiwanda (Cape Lookout is between them, and rounds out the “Three Capes”) where you’ll have great coastal views around every bend in the road. If you’re following this itinerary as we’ve laid it out, you’ll be heading north to south.

  • Cape Meares is your first stop, and there are two things to check out. First is the Cape Meares Lighthouse, which is the shortest lighthouse on the Oregon Coast. However, it has an impressive lens that was installed in 1890. The second thing not to miss is the Octopus Tree (it’s a weird looking tree with eight branches, hence the name) and the viewpoint right past it that looks out over the beaches to the south, including Short Beach. It’s a short walk from the main parking lot.
  • Cape Lookout is your next stop, and is our personal favorite of the three. The highlight, by far, is the hike out to Cape Lookout . It’s a relatively easy hike that hugs the cape, which narrows as you get further and further out onto it before the trail ends at its western tip, where the views are amazing and you can hear the seals frolicking on the rocks below. It’s also a good place for whale watching in spring, because it’s about as close to the migrating mammals as you can get.
  • Cape Kiwanda is the last of the three capes, and it’s a little different. It’s very popular with surfers, and you can drive out onto the beach, which means it’s a slightly different crowd that includes fishermen and boaters. From the parking lot, the main attraction is up and to the right of the beach, where you can hike up onto the cape for some great views in both directions. You’ll be hiking up in deep sand, so it’s harder than it looks. Make sure to catch the hang gliders, if they’re out, who use the northern end of the cape as a jumping off point. 

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Tillamook Cheese Factory: The Tillamook Cheese Factory is legendary. Not only is there a cool educational experience where you can see how they make the cheese, but there are some truly great food options, including a huge ice cream scoop shop. If you’ve never had their ice cream before, it’s incredibly creamy. That’s their whole thing. The chocolate peanut butter swirl is Alysha’s favorite, with thick, creamy swirls of peanut butter tucked into their chocolate ice cream.They also have a retail store here, where you can buy all of their cheeses, including some of their hard-to-find reserve varieties, along with a selection of other local products. If they have them, do not miss their cheese curds, which are only available at the factory and are incredible (we’d never had them before we bought them a few years ago and fried them up post-hike over our camp stove – incredible). 

More Cheese: There’s actually a second cheese destination down the road – Blue Heron French Cheese Co – though we weren’t nearly as impressed with the presentation. The cheese – which leans towards French style – is really good, though. 

Hiking in Lincoln City: Technically this isn’t Tillamook – it’s 30-45 minutes south – but we’re including it here because two of our favorite hikes on the Oregon Coast are in and around the sleepy coastal community of Lincoln City. The first is Cascade Head , which is maintained by the Nature Conservancy (no dogs allowed). It’s a great hike that climbs through the forest and emerges onto a (very windy) bluff over the ocean, which you can climb up for some great coastal views. It’s windy as you get out onto the coast, so be prepared. The second is God’s Thumb , which is a short hike from the north end of Lincoln City that takes you out to a point, which looks out over the Oregon Coast both north and south. Along the loop, you’ll pass the Knoll, where you’ll have a great view of the neverending sandy beach that stretches out to the south. 

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Drive Time / Distance from Tillamook to Newport: 1 hour 30 minutes / 70 miles

Where to Stay in Newport: We haven’t stayed there ourselves yet, but the Inn at Nye Beach has been on our list for years now. 

Newport is the biggest city on the central Oregon Coast, and has the best selection of places to stay, restaurants, and other amenities like grocery stores before you get into the more rural southern Oregon Coast. 

The structure for today is essentially using Newport as a home base to continue your road trip south along the coast past Newport (which is one of our favorite stretches of the Oregon Coast) and then returning to Newport for the night to set yourself up for a long drive the next day. 

Just south of Newport, the coast starts its transformation from the very developed, very tourist-friendly northern Oregon Coast to the more rugged southern Oregon Coast, which is rockier, less-traveled, and offers a little more peace and quiet than places like Cannon Beach and Seaside. 

From Newport, you can hit one of the most scenic drives on the coast – the area around Cape Perpetua and Heceta Head – before returning to Newport for the night to eat some fresh seafood and check out one of the many beaches in town. 

What to Do Around Newport

Here are our favorite things to do in and around Newport. 

Devil’s Churn: A short stop where you’ll hike down to an overlook with a view of an inlet that is partially covered at the end. Which means at high tide, if you’re lucky, the waves coming in will meet the waves going out and create an explosion of water.  

Cape Perpetua: The view from the top of Cape Perpetua is one of our favorite views on the coast, and it reminds us a lot of Big Sur down on the California Coast (at least on a sunny day). You can hike from the lower road up to the top , which is a nice workout, but you can also just drive to the top (which we didn’t know until we got up there, sweaty and huffing and puffing). There really isn’t a reason to do the hike other than a workout – there aren’t really any additional views you get by hiking. 

Heceta Head Lighthouse: This is one of the most beautiful lighthouses on the coast, and it’s easily accessible from the parking lot. It sits on a 1,000 foot headland that towers over the Pacific, and they have tours of the lighthouse, a charming B&B in the old light keeper’s home, and tidepools and trails to explore. You can hike out to Hobbit Beach from the lighthouse, which is a nice little trail that follows the coast to a sandy beach. 

Sea Lion Caves: We drove past this place on our first trip, saw a line out the door of a tiny little touristy-looking hut, and said “look at those suckers!” Then we learned what it actually was later on from some Oregonians, and were at least a little bit disappointed that we didn’t stop in. If you want to see sea lions, this is the place to do it. That hut sits over an elevator that takes you down hundreds of feet to the water level, where there’s a sea cave – America’s largest, in fact – filled to the brim with barking sea lions. Skeptical? Here’s the webcam where you can see for yourself. They’re open 9:00 am – 4:00 pm 363 days a year, and it costs $16 for adults, $10 for kids (under 4 are free!), making it a little bit pricey. 

Exploring Newport: Newport is probably best known for its world-class aquarium – the Oregon Coast Aquarium – which we stopped at and immediately turned around when we saw the flood of small children (it would be a good family activity, though!). There are two lighthouses in town, and the Yaquina Head Lighthouse is at the northern end of town, and is well worth a stop (the Yaquina Bay Lighthouse is less impressive). Definitely head down to the charming Historic Bayfront for dinner and the shops there ( here on Google Maps) and head out to Agate Beach ( here on Google Maps) for a good view of the lighthouse. 

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Drive Time / Distance from Newport to the McKenzie River: 3 hours / 130 miles

Full disclosure here: this part of the itinerary requires a long drive, but we think it’s worth it because this part of Oregon might just be our favorite in the entire state. 

The McKenzie River Scenic Byway follows the path of, you guessed it, the McKenzie River, which is one of Oregon’s many important rivers. For your purposes, we’d recommend driving it from the I-5 corridor (you’ll take Highway 126 from Eugene, which connects you to Highway 242) all the way to the eastern end in Sisters. 

It’s a gorgeous drive, littered with waterfalls, tight switchbacks, alpine lakes, and lava flows. 

There are a few things you need to know about this stretch. First, it’s closed outside of summer and early fall (usually open between July and October).

Second, it’s a narrow one way road, so it might not be best for RVs or trailers . 

This is going to be a long day of driving, but ultimately we think it’s worth the journey. At some point, you have to cross over the state from the coast over to the Cascades, and it’s going to take 2-3 hours, depending on how you do it. 

We went back and forth on whether or not to add a night here in Eugene, which would cut down on the drive time, but ultimately we think your time is better spent on a long drive today to give yourself some extra time in other places (which we think are more worthy of your limited time than Eugene).  

Note: You’ll spend the night in Bend tonight, so we’re skipping the “where to stay” section here. 

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What to Do Along the McKenzie River Scenic Byway

Also, if you follow this itinerary as we’ve written it, you’ll be approaching from the west (coming from the Eugene area). We’ve organized the stops from west to east for that reason. 

Proxy Falls: Over the course of this trip, you’re going to see a bunch of incredible waterfalls, especially as you get into the Columbia River Gorge later in the itinerary. Proxy Falls will likely be in your top three. It’s a short hike – roughly 1.5 miles – that takes you to a massive waterfall that cascades down the mossy rocks into Proxy Creek. You can do a loop that takes you to both Lower Proxy Falls and Upper Proxy Falls. The lower falls is the more impressive of the two, and the view from the base is incredible. 

Scott Lake: This pristine lake is one of the spots we’re hoping to return to this summer. It’s a gorgeous lake with a perfect reflection of the Three Sisters (really two of the three sisters), one of the most distinctive natural features of central Oregon, and a bunch of first come, first served campsites along the lakeshore. However, the tradeoff here is the mosquitoes, which are intense in the early summer. For your purposes, we’d park along the lake and walk out to the western shore to get that reflection picture. It’s best in the afternoon, when the sun is behind you. 

Dee Wright Observatory : As you ascend the tight switchbacks along the road as you pass Scott Lake, you’ll notice an abrupt change in the landscape. In what seems like a few minutes, you’ll go from dense evergreen forests to an open, rocky landscape. That shift is a result of a massive eruption of the Belknap Crater two millennia ago, and that dark rock stretching out as far as the eye can see is the resulting lava flow. The Dee Wright Observatory is an excellent stop not only to admire the lava flows, but because it gives you a great overview of the numerous rocky peaks surrounding you. This, my friends, is the heart of the Cascades in Oregon, and you’ll see the Sisters, Broken Top, Mount Washington, and Mount Jefferson, along with a handy key atop the Observatory to help you identify which is which. 

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Sisters: Sisters represents the end of the McKenzie River Scenic Byway, and the beginning of central Oregon and the high desert, which stretches for hundreds of miles to the east until you get into the Wallowas in eastern Oregon. 

Sisters itself is a cute little town that’s a great base for adventures into the nearby Three Sisters Wilderness. 

It’s a vaguely western-themed town, with some great spots to eat and drink ( Sisters Coffee and Sisters Meat and Smokehouse are good stops) and a cute little downtown area where you can do some window shopping. 

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Drive Time / Distance from the McKenzie River to Bend: 1 hour 30 minutes

Where to Stay in Bend: This choice basically comes down to whether you want to be downtown in the heart of all the action, or in a quieter locale. Stay at the Oxford Hotel in Downtown Bend for the best location in the middle of the action. Stay at LOGE Bend – we’ve stayed at other properties they own before – if you want to be right near the Cascade Lakes Scenic Byway.

Over the past decade or so (though it seems like it happened overnight), Bend has gone from being somewhat on the map, to being one of the most famous outdoor destinations in the western United States. 

As you drive through the Cascade Mountains into the heart of Central Oregon, you’ll notice that the landscape starts to change.

First you hit the eastern foothills, which are notably more dry than the western foothills, and as you continue to Bend and beyond, you’ll be right in the heart of the high desert that stretches across Central Oregon. 

Bend is perfectly placed between the mountains and the high desert. Within 45 minutes or so, you can be in the heart of the alpine paradise in the Cascades, or hiking through the desert dodging rattlesnakes in Smith Rock State Park (more on that in a second). 

Within 45 minutes or so, you’ve got great hiking, cycling, skiing, watersports, and more. Plus, Bend itself has a pretty good food scene, the Deschutes River and all the watersports it has to offer, and perhaps the best selection of breweries in the country. 

What to Do in Bend

Here are some things to do in Bend, including some of the things to do just outside of town along the Cascade Lakes Scenic Byway. 

Hikes Around Bend: Within the Bend city limits, there are a few good hikes (we’re not counting the hikes in the mountains or at Smith Rock, which we have separate sections for below). Pilot Butte is right in the middle of town, and after a quick ascent you have a panoramic view of the surrounding landscape that serves as a nice introduction to Central Oregon’s geography. To the west, you’ll be able to see the snow capped peaks of the Cascades (there’s a topographic map to help you identify which peak is which). To the east, it’s a lot of flat land. We also have hiked pieces of the Deschutes River Trail , which heads south out of town along the river. You could follow the trail for miles and miles, but there’s a nice 2.7 mile loop that focuses on the part of the trail near the Old Mill District that would be a lovely way to spend a morning. It would look something like this . If you want something a little longer, continue south from Farewell Bend Park, which is where the trail gets a little less developed. For more information, read our guide to hiking in Bend .

Explore Downtown Bend: Downtown Bend is centered around Drake Park along the Deschutes River (there are several areas that could be confused as “downtown” so we wanted to clarify). There’s also the Old Mill District, which is a little bit south (and has more chain retailers and Red Robin vibes, if you know what we mean), and the Box Factory, which is between them. In downtown Bend, go to Lone Pine for coffee, The Lemon Tree for brunch (it’s popular so go early), and Bontà for gelato. Then, poke your head into the many shops and boutiques along NW Wall and NW Bond. 

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Brewery Hopping: Bend, like Portland, is known for its breweries. And like Portland, there are way, way too many breweries to visit in just a couple days. Here are a couple that we like for one reason or another.

  • Deschutes Brewing : In many ways, the OG Craft Brewery in Bend that set off the craft beer craze in Oregon. It’s still owned by the original owners (rather than Anheuser-Busch), which is cool. They do tours (which we’ve done and enjoyed), and they have an onsite taproom with beers that you can’t find elsewhere.
  • Silver Moon Brewing : A cozy taproom outside of town – we like them for their Thursday trivia nights! They have a cool space that has both indoor and outdoor seating with a lineup of live music in the summer. They also have a couple of food trucks onsite.
  • Crux Fermentation Project : Our friends who are beer nerds think this is the best beer in Bend (though they also note that there’s too many and they’re too different to really choose). What we like about them is their HUGE outdoor terrace, which is a perfect place for some cold beer after a morning of hiking.  

Cider in Bend: If you’re more into cider (we are!), the small town of Tumalo just north of Bend has a couple of our favorite cideries in Oregon, and they’re just around the corner from each other. The first is Tumalo Cider , which has a nice taproom and great, dry ciders. The second is Bend Cider Company , which has a new-ish taproom a couple of blocks away. They do fun flavor combinations featuring fruits and botanicals (but not too sweet!) – we liked the Blackberry Ancho we tried recently. There’s a food cart pod across the street from Tumalo Cider which would make a good stop for lunch between cider tastings.

Tumalo Falls: Honestly, the hike to Tumalo Falls kind of sucks. But the waterfall is cool, so there’s that! It’s a 97 foot high plunge into Tumalo Creek, and if you do the six mile hike, you’ll reach the viewing platform and realize that it’s a five minute walk from the upper parking lot. We’d drive to the parking lot and check out the falls, saving your energy for a more interesting hike (there are many!) later. 

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Explore the Cascade Lakes Scenic Byway: This scenic drive (also known as Highway 372) leaves Bend, heading southwest out into the alpine paradise that is Deschutes National Forest. Skiers and snowboarders familiar with Oregon will know this stretch because it takes you out to Mount Bachelor, one of the state’s premier skiing destinations. Which, if we think about our other favorite hiking spots in the Pacific Northwest, is a great indicator of a good summer hiking destination. It’s worth spending a day driving the byway, starting in Bend and working your way down to Elk Lake before returning the way you came. You could also do a loop, taking NF-40 back towards Bend, but we’d prefer driving the more scenic byway both ways. This is a very popular stretch, and there is a permit you’ll need to enter during the peak summer season. 

Hiking Along the Byway: The Cascade Lakes Scenic Byway is full of great hikes, particularly as you get out past Mount Bachelor. Here are a few good ones. 

  • Green Lakes Trail : Potentially our favorite hike in central Oregon (technically it’s in the Cascades, so does that count as central Oregon?), this hike has everything we love about hiking in Oregon . Following a babbling creek the entire way, which is the perfect white noise for a hike? Check. Pristine alpine lake (really, lakes)? Check. All sorts of peaks to admire? Check. It’s 9 miles, but it’s an easy 9 miles, we think.
  • Tumalo Mountain Trail : A tough ascent, but the views from atop Tumalo Mountain are worth the sweat. You’ll have Mount Bachelor, the South Sister, and Broken Top right in your face, with various other peaks peeking out behind them. It’s basically straight up, straight down.
  • If you’re really up for a challenge, there are two excellent but difficult hikes here: Broken Top & No Name Lake and the South Sister . Both are very difficult, and should not be underestimated. The South Sister is going to be better if you can backcountry camp the night before at Moraine Lake or Green Lakes, which cuts down your ascent (but requires an extra night of backpacking, and all the associated gear). 

Sparks Lake: We love Sparks Lake. The main photo on the homepage of this site (at the time of writing) was taken there on an early summer morning just after sunrise. Head to the day use area, park, and walk along the southeastern shore of the lake, where you’ll be treated to an absurdly good view of the South Sister and Broken Top, with a reflection in the still water of the lake if you’re lucky. 

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Day 9: Smith Rock State Park (and Drive to Government Camp)

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Drive Time / Distance from Bend to Smith Rock State Park: 36 minutes / 23 miles

I will never forget the first time that I laid eyes on Smith Rock State Park during a spring trip to Bend with friends. I had only really ever been to Bend to go skiing in the winter at that point, which had us out in the forest to the city’s west at Mount Bachelor. 

Smith Rock, with its winding river snaking its way between orange-hued rock formations, looks like it belongs somewhere in Utah or Arizona, not in Oregon. At least in my mind, having never explored Oregon east of the Cascades at that particular point in my life. 

Bend is perched in the eastern foothills of the Cascades, and it is situated between the lush evergreen forests that cover the western part of the state, and the high desert that covers most of central and eastern Oregon. 

Remember at the beginning of this guide, when we said that Oregon is the ninth biggest state in the country? Bend is about 25% of the way from the western border (the coast) to the eastern border with Idaho. Which means the high desert stretches for a LONG time from Bend to the east. 

Smith Rock State Park is a destination that is definitely worth stopping at, but it’s not worth an entire section with separate things to do and places to stay. Instead, we’d recommend a stop on the way from Bend up to Mount Hood. It’s a perfect location for that. 

There’s really only one hike in Smith Rock State Park – though you can do it two ways – and that’s the Misery Ridge Trail . It’s accurately named, because the initial ascent up to Misery Ridge is brutal, especially on a hot summer day with full exposure to the sun. 

The views from the top of the ascent, though, are worth the price of admission. You’ll have a panoramic view of central Oregon, with the snowy peaks of the Cascades to the west, and the high desert stretching out as far as the eye can see to the east. 

On the descent, you’ll pass Monkey Face, a very popular destination with rock climbers. It is also accurately named, because from a certain angle, it looks exactly like the face of a monkey. 

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The trail descends back down to the river, where you can either head left to return on the River Trail (shorter and flatter) or right to continue on the Summit Trail (longer with better views and more climbing) to finish the loop.

Note: This is another place where you’ll stop along the way to another destination – in this case Mount Hood – so you’ll spend the night in and around Government Camp after your exploration of Smith Rock. 

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Drive Time / Distance from Smith Rock to Mount Hood: 1 hour 40 minutes / 86 miles

Where to Stay at Mount Hood: There aren’t that many places to stay here, but you do want to be in or around Government Camp on the south slopes of the mountain. There’s a Best Western , a campground at Trillium Lake that we like, and a bunch of nice cabins in the woods to choose from. 

Mount Hood is our favorite hiking destination within a couple of hours of Portland. We fell in love with it on that first road trip that eventually led us to move here, and we go back there as often as we can. 

Matt is from Seattle, where the towering peak of Mount Rainier is a near constant reminder of the natural beauty that lives just outside of the sprawling city (and also a constant barometer of the weather – “is the mountain out?” is a common question to evaluate whether it’s a nice day in Seattle). 

Mount Hood plays a similar role for Portland, and we often have a similar conversation around Portland around whether Hood is out. 

During the winter, Mount Hood is home to some of Oregon’s best skiing. Then, when the snow melts in the late summer, it turns into a veritable alpine wonderland, with wildflowers blooming, roaring waterfalls, and stunning vistas of Mount Hood around every bend in the trail. 

The part you’re going to want to focus on here is the area in and around Government Camp , on Mount Hood’s southern side. 

That’s where all the action is, though that’s not to say there aren’t worthwhile places to visit on other sides of the mountain. 

By focusing there, you’re also nicely positioned for the next stop on your itinerary, Hood River, where you’ll just hop back on Highway 26 and continue north to Oregon’s northern border. 

What to Do at Mount Hood

Here are some of our favorite things to do and see near Mount Hood.

McNeil Point (or Bald Mountain via Lolo Pass): For some of the best views in Oregon, you should hike one of these two trails. However, be warned, the hike up to McNeil Point is no joke. Not even a little bit. We did it at the peak of our hiking powers, during a summer where we were hiking 7-8 miles almost every day, and it kicked our butts. With that warning out of the way, it’s a fantastic hike. It takes you up to an alpine wonderland on Hood’s northwestern slope where you’ll have unobstructed views of the mountain, and you’ll feel like you’re close enough to reach out and touch it. The full hike to McNeil Point is a 10 mile lollipop – you should do the lollipop section counterclockwise because it involves a scramble that is easier to do uphill (you can also go around and make it an out and back, but it’s about 2 miles longer). 

Our favorite view in Oregon is the view from Bald Mountain: You’ll find it plastered all over this website – which you can access either on the way up to McNeil Point, or as a different, much easier hike from the Lolo Pass Trailhead. That’s a good shorter option that is more accessible for more hikers. 

Ramona Falls : If you want a waterfall hike, this is it. Don’t let the 7 miles scare you off – it’s a pretty easy hike with the exception of the crossing of the Sandy River, which used to have a bridge, but has since been relegated to “I don’t know, find your own way across.” It’s not an easy one, though it is worth noting that hundreds of hikers do it every day in the peak of the summer. There are various logs, and some narrower sections of the river a bit upstream from the trail where you can make the crossing. We wouldn’t take our dog, though. Ramona Falls, unlike some of the waterfalls in the Columbia River Gorge, is a wide cascading falls that dribbles down a rock wall rather than plunging down into a pool. Still, it’s very impressive, and it’s 120 feet tall – tall enough that it’s hard to get the whole thing in frame on a photo without a wide angle lens. 

Timberline Lodge and the hike to ZigZag Canyon: The iconic Timberline Lodge is an uber-rustic lodge that is reminiscent of the various national park lodges in the American West. It was built in 1937, and has since been declared a National Historic Landmark. If you’re up for a splurge, their rustic rooms would be a fun place to stay. However, even if you’re not staying here, it’s worth coming up to do some exploring on the trails around the lodge (in the summer, anyway, it’s a ski resort during the winter months). Our favorite of the bunch is a piece of the Timberline Trail, which circumnavigates Mount Hood, and it’s the stretch between the lodge and Zigzag Canyon . It’s a beautiful, somewhat easy hike that ends with a view of the peak up a canyon. 

Trillium Lake: This is our favorite campground in Oregon, although it’s also one of the most competitive. We’ve camped here a few times, and we’ll do it again. The draw here is the excellent views of Mount Hood, often reflected in the surface of the lake, which you can find from the southern end of the lake near the day use parking. It’s also a great place to bring watercraft like kayaks and stand up paddleboards in the summer. 

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Drive Time / Distance from Government Camp to Hood River: 50 minutes / 43 miles

Where to Stay in Hood River: Hood River is a very nice little downtown area, and there aren’t that many places to stay downtown. We actually like staying across the river in Washington, either at the Society Hotel in Bingen or at the lovely RubyJune Inn (a very charming B&B in a tranquil setting run by lovely people). 

The Columbia River Gorge runs along the northern border of Oregon (it separates Oregon from Washington State), and has the highest concentration of waterfalls in the state. 

Depending on how good your memory is (and how long ago high school was for you), you may remember the Columbia River from your days learning about Lewis and Clark, because it’s the river that they came up as they made their way out to their final destination just south of Astoria. 

Living in Portland, the Columbia River Gorge is essentially our backyard. It takes 30-40 minutes for us to get out there, and when we’re looking for an easily accessible hike for a random Thursday morning, this is generally where we’re heading. 

It’s also on our itinerary for every single first-time visitor who comes to Portland to visit us. 

There is a nice mix of different hikes in the Columbia River Gorge , from easy waterfall hikes to hikes that climb to the rim of the Gorge, where you’ll find dramatic vistas out over the Columbia River and the gorge beyond. 

Hood River is a town in the Columbia River Gorge, and it is perched at a crossroads of sorts. It sits at the point where the wet, temperate climate of western Oregon transitions to the dry, more extreme climate of the high desert in eastern Oregon. 

To the west, you’ll find some of the best waterfalls in Oregon. To the east, the high desert. And both north and south are the Cascade Range, and places like Mount Hood and Mount Adams. 

There are a bunch of great things to do in Hood River, and that list grows longer when you include the fertile Hood River Valley and its fruit trees as far as the eye can see and the wineries along the Columbia River. 

Hood River is a great home base to use to explore the Gorge and the fertile Hood River Valley, which is what you’ll be doing for this stretch of the itinerary. 

Note that we’ve split the “what to do” sections below into Hood River and the Columbia River Gorge to make it easier for you to plan and group things together.

What to Do in Hood River

Here are a few of our favorite things to do in and around Hood River.

Tamanawas Falls: This hike is on the eastern slopes of Mount Hood, and would be an excellent stop between Government Camp and Hood River. It’s right on Highway 26, and it’s a nice, easy hike up to a spectacular waterfall. Parking is limited, so you’ll want to get there early, or be prepared to wait for a spot in the tiny lot – parking along the highway is illegal, and we’ve seen many people get tickets here. 

Read More: Everything You Need to Know to Hike the Spectacular Tamanawas Falls Trail

Drive the Fruit Loop: The Hood River Fruit Loop is a perfect half-day activity near Hood River that takes you through the fertile Hood River Valley, with apple and pear trees as far as the eye can see (with backdrops of Mount Adams, Mount St. Helens, and Mount Hood). There are a bunch of worthwhile stops here, but our favorite is Draper Girls Country Farm , which does u-pick cherries for a short window in the summer, and has all around excellent produce more or less from spring to fall. They have a lovely back patio area with great views of Hood, and a lush collection of various fruit trees. Plus, a great selection of locally made jams, honeys, and other stuff inside the shop. 

Wine Tasting near Hood River: The area around Hood River, both on the Oregon side of the Gorge, and on the Washington side, is a great place to grow grapes and make wine. There are a bunch of wineries in Hood River itself ( Hood River Common House is a good spot), but the real way to do it is to hop in the car and drive out to one of the wineries dotting the landscape around Hood River. We like the Gorge White House (not the best wine and cider, but the setting is amazing) and Loop de Loop (the friendliest wine makers and the best dog, plus an amazing view), and have also heard good things about AniChe Cellars , Le Doubblé Troubblé , and Analemma Wines (this one came highly recommended from the folks at the Ruby June Inn, where we stayed on our recent trip). 

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What to Do in the Columbia River Gorge

Here are our favorite stops in the Columbia River Gorge.

Wahclella Falls: This is the best bang-for-your-buck waterfall adventure in the Columbia River Gorge, we think. Multnomah Falls is great, yes, but it’s an absolute zoo at all hours. The short and easy hike out through a canyon with steep rocky walls here weeds out most of the visitors, and you end up at a beautiful waterfall that tumbles off of a ledge into a pool 65 feet below. 

Read More: Everything You Need to Know to Hike the Wahclella Falls Trail

Drive The Historic Columbia River Highway: The Historic Columbia River Highway runs from the town of Dodson, just west of Bonneville (and the dam of the same name), all the way to the town of Troutdale, which is just east of Portland. It’s a windy two lane road that parallels I-84, and is the original road that was used to traverse the Gorge on the Oregon side. Our recommendation would be to drive it from Multnomah Falls to its western terminus, because there are routinely huge traffic jams along the road at the base of Multnomah, and it’s better to park in the big lot along I-84. 

Multnomah Falls: Multnomah Falls is the queen of the waterfalls in Oregon. It’s by far the most impressive waterfall in the state, we think, and it’s actually the biggest tourist attraction in Oregon thanks to its location about 40 minutes away from downtown Portland. It’s a two-tiered waterfall that, all-in, falls 620 feet down from the top of the rocky ledge high above the viewing platform. The only issue we have with Multnomah Falls is the fact that, at any given moment, you’re likely to be sharing the experience with around 1,000 of your closest friends. It’s worth seeing, but there are so many other waterfalls in the Gorge to get to with a fraction of the visitors (especially if you’re willing to hike a little bit). Oh, definitely park at the bigger parking lot along the freeway ( here on Google Maps) – the smaller lots at the base of the falls are an absolute nightmare, and we’ve seen massive backups along the Historic Columbia River Highway of people just waiting to get a spot. The bigger lot has more parking, and you just have to walk a few hundred feet to get to the falls. 

Latourell Falls : Lower Latourell Falls is one of the most scenic waterfalls in the Gorge after Multnomah, particularly in the winter when the water level is high AND there’s a bright greenish-yellow moss covering the rocks on either side of the falls. The lower falls is the more impressive, we think, as it falls 225 feet off of a ledge in one single drop. There’s a nice wooden bridge at the base of the falls, which is a short hike from the trailhead that is a must-do, that is a good spot for pictures. There’s a nice, relatively easy two mile loop hike that takes you up to the Upper Falls and down around to the base of the lower falls that is a worthy excursion if you have the time and energy. 

The Vista House & Portland Women’s Forum Scenic Viewpoint: These are two excellent viewpoints at the western end of the Historic Columbia River Highway to cap off a day full of great views. Pictures are worth 1,000 words here, we think, so here’s a few we’ve gotten from up here. 

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Day 14: Explore Portland 

how to travel to oregon

Drive Time / Distance from Hood River to Portland: 1 hour / 63 miles

Where to Stay in Portland: Portland is – by far – the biggest city in this guide, so we’d recommend reading our in-depth guide to choosing a place to stay in Portland for the information you need to make the best choice for you (which takes more than a couple of sentences).

What can we say about Portland? We have fallen head-over-heels in love with our new home. Everyone always talks about the “weirdness,” which we have come to understand as an implicit permission to be whoever you want to be. 

That idea flows through to the unique small business culture that exists in Portland, where you can find all sorts of locally made foods, crafts, and home goods.

The funny part about Portland is that there aren’t really any big name tourist attractions. Seattle has the Space Needle, San Francisco has the Golden Gate Bridge, and Portland has… a donut shop and an independent bookstore? But, honestly, that’s kind of why we love it. It’s not that there isn’t a lot to do – there’s plenty of amazing things to do in Portland. 

The food scene? The best on the west coast (except for maybe L.A.). There’s a culture of innovation – which we think is at least partially driven by the food cart scene that allows for low-cost experimentation (versus opening a brick and mortar location). 

The access to the outdoors? Between the excellent parks in Portland and the access to the mountains, Gorge, and coast, it’s hard to beat.

We’re in love with our home, and think you’ll like it too. 

Unfortunately for you, your time here is limited, and we’ve intentionally chosen to weight this road trip towards Oregon’s natural beauty, which means you’re left with about a day, maybe a day and a half to explore the biggest city in the state.

If you have an extra day or two, it’s absolutely worth adding time here.  

What to Do in Portland

Now, there are way too many things to list here, so we’re going to focus on our top five here.

Powell’s City of Books : The fact that we’re starting with an independent bookstore – the largest in the world, no less – tells you just about everything you need to know about Portland. It’s right in the heart of downtown Portland, and is an astounding collection of books from all genres. This place is amazing, and even since we’ve lived here I can’t walk out of here with at least one book. I bought a light blue Powell’s Books t-shirt on clearance almost a decade ago that I wear often, and every time I wear it outside of Portland (usually in Seattle) at least one person stops me to chat about how much they love Powell’s. They have an extensive collection of books, including big sections dedicated to fantasy/sci-fi, Pacific Northwest history, and graphic novels. We especially like the staff picks section in the entryway, which is a nice way to see what the staff are reading and recommending at the moment. 

The International Rose Test Garden : Washington Park – which is the park where this rose garden is located – is the best park in Portland, and is home to a bunch of different attractions including the Oregon Zoo and the Portland Japanese Garden. But the Rose Garden, which is both free and spectacular, is the best of the bunch, we think. There are 10,000 roses here, and when they’re in full bloom between roughly May and September (sometimes longer), it’s quite a sight to behold. 

Breakfast / Brunch in Portland: Portland is an excellent food city in general, especially when you consider prices are going to be about 25% lower than other cities on the west coast. However, it really shines in the morning, when you’ll find some world-class breakfast and brunch options. 

Now, you might expect to see Voodoo Donuts on this list. 

The novelty donuts are fun, yes, but it’s far from undiscovered, and there are honestly much better doughnuts to be had in Portland. Like, a lot of them. Go to Blue Star , Doe Donuts , Coco Donuts , or Petunia’s Pies and Pastries (for gluten free and vegan donuts) if you’re in and around Downtown Portland. 

Here are some of our favorites, in no particular order. 

  • Fried Egg I’m in Love : Award-winning breakfast sandwiches! They have a food cart in downtown Portland, along with a brick & mortar shop on Hawthorne Blvd in Southeast Portland and up on Mississippi Avenue.
  • Ken’s Bakery : The best bakery in Portland, probably. It’s in northwest Portland, and is a local favorite with a rotating selection of pastries that you can see them making right behind the register. Good sandwiches for lunch, too, but the hero is the pastries in the morning.
  • Pip’s Original Doughnuts & Chai : Go for the mini donuts (they are NOT donut holes, Matt!) with innovative flavors, stay for the incredible chai. There’s a perpetual line, especially on weekends, so go when they open if you can. Alysha LOVES their chai (get a chai flight!). 

Explore The Eastside: While most of the tourist attractions like Powell’s and the Rose Garden (though Powell’s has a location on Hawthorne) are on the west side of the river, we actually like the east side of the river more. We’d divide this large and sprawling area into three distinct areas. If you’re staying downtown and don’t have a car, your best bets are going to be:

  • The Central Eastside: Just over the river from downtown, this area is an old industrial district that has become a great place to spend an afternoon, with all sorts of places to eat and drink. We like Schilling Cider House (for 50 taps of different ciders), Cascade Barrel House (for beer), and the Revolution Hall Rooftop for drinks with panoramic views of Portland and Mount Hood).
  • Southeast Portland: Our neighborhood! Centered on Hawthorne Blvd and Division St, this stretch runs straight through a residential neighborhood and is full of places to eat and drink. Fried Egg I’m in Love (breakfast sandwiches), Cibo (pizza), Lauretta Jean’s (pies), Pinolo Gelato (gelato), Magna Kusina (Filipino), and Oma’s Hideaway (Malaysian / Singaporean food) are the spots we’d hit.
  • Mississippi Avenue: Where we used to live! The stretch along Mississippi Avenue might be the most bang-for-your-buck in terms of the amount of bars and restaurants packed into a relatively short stretch. For food, Lovely’s Fifty-Fifty (of Chef’s Table fame), Kate’s Ice Cream (plant-based ice cream), and the food cart pod at Prost . For drinks, go to Interurban . For shopping, don’t miss the Meadow , a store that we go to far too often with salt, chocolate, and bitters.
  • The Alberta Arts District: The furthest from downtown Portland, Alberta Street is one of the main corridors in northeast Portland. Similar to the other places on this list, it’s packed with great food, drinks, and coffee. For coffee, don’t miss Proud Mary (our top coffee shop in Portland for fun single-origin coffees) and Barista . For food, go to Tin Shed Cafe for brunch, Zilla Sake for excellent sushi and sake, and Matt’s BBQ Tacos for…tacos. For drinks, Bye and Bye for good drinks and vegan food, and Great Notion Brewing for beer (and the aforementioned Matt’s BBQ Tacos, which operates on their patio). 

For more, we’d encourage you to head over and read our other Portland guides.

What to Add with More Time in Oregon

Like we’ve said time and time again, two weeks is not really enough time to see everything there is to see in Oregon. Here are a few more things to consider adding if you happen to have more time. 

More Time in Portland (+1-2 Days)

how to travel to oregon

As we mentioned above, we intentionally decided to weight this itinerary towards Oregon’s natural beauty and have you spend the vast, vast majority of your time outside of cities. 

Which, unfortunately, leaves you with just over a day to explore Portland. 

Ideally, you’d spend two or three days in Portland, which is one of the most underrated food cities (quickly transitioning to “appropriately rated”) cities in the country. 

There’s a strong culture of experimentation and innovation in Portland’s food and drink scene that puts it on the leading edge of food trends that make it a great place for people who love to eat to explore.  

With an extra day or two, you can experience the things that we love about Portland at a more comfortable pace – the amazing green spaces inside the city, and the thriving food and drink scene to name a couple. 

If you have the extra time, we have guides to 2 days in Portland and 3 days in Portland (which includes a half day trip to the Gorge, which you could replace with the trip to Silver Falls just below this) which will give you a play-by-play of exactly how we’d spend your time. 

Day Trip to Silver Falls State Park (+1 Day)

how to travel to oregon

Silver Falls State Park is a hair over an hour south of Portland, and it’s home to one of our favorite hikes in the state – the incredible Trail of Ten Falls . Which, as you might imagine, features 10 waterfalls over the course of a relatively easy eight mile trail. 

If you want waterfalls – and especially if you’re here in the spring and early summer when the water is high – this is as close to a must-do as it gets. 

After your hike, you can meander through the eastern end of the Willamette Valley on your way back to Portland, stopping at Bauman’s and E.Z. Orchards for farms and cider (and apple cider donuts!). 

The tiny town of Silverton is a nice place to stop for lunch after the hike (or just wait until you get back to Portland and check off some other places there!).

If you do want to stay overnight, the campground at Silver Falls is really nice. However, other than that, there’s really not a whole lot of places to stay nearby, and you’re probably better off making it a day trip and staying in Portland for another night. 

Crater Lake National Park (+1-3 Days)

how to travel to oregon

So you want to add Crater Lake National Park to your Oregon trip?

Well, we have good news and bad news. 

The good news is that it’s totally doable as long as you have a little extra time. 

The bad news is that it’s only really accessible for a few short months a year, and it’s not really convenient even when it’s at its most accessible. It’s at the southern edge of the state, and it’s fairly far from just about everything else on this itinerary.  

To add Crater Lake to the itinerary, you’re going to want to do it after Bend. It’s about 90 minutes from Bend to the north rim of Crater Lake, which doesn’t seem so bad, right?

However, there is one major caveat here, and that’s the fact that the rim road that circles around to the north end of the rim is closed during the winter and early spring due to snow. 

It will start to open in early spring, but when exactly that happens totally depends on the year. 

That’s an issue to keep in mind because Bend is north of Crater Lake. The only way to access the small slice of the park that’s open between November and April (roughly), which is on the south rim, is to enter the park through the south entrance. Which is about three hours from Bend. 

We would only really recommend adding Crater Lake during the summer and early fall (call it June through October) when roads will be mostly open, and hiking trails will be mostly snow-free.

Add it as an overnight trip from Bend, and continue along on the McKenzie River Scenic Byway as written. 

What to Do with Less Time in Oregon

With less time – 7 or 10 days in Oregon – we’d make some adjustments and be more focused with your time. With 5 days in Oregon, we’d go ahead and spend the entire time in Portland, doing day trips out to the Gorge, the Coast, and Silver Falls to fill your time (you’d want to rent a car for that trip).

With 7 days , we think you have time for a nice little loop that encompasses Portland and the mountains OR the coast, but probably not both.

If you absolutely have to see both, you could add a day on to do a day trip out to the coast (Cannon Beach or Astoria) or the Columbia River Gorge (Hood River).

With 10 days , you have enough time to comfortably do a figure-8 that includes the mountains (Hood River and Mount Hood) and the coast (Cannon Beach and Astoria). 

Here’s a day-by-day breakdown of what those itineraries might look like. 

7 Days in Oregon: The Mountains

Here’s what a perfect 7 days in Oregon might look like, focused on the northwest corner of the state around Portland. 

Add a day if you want to do a day trip out to the coast (and read our guide to the best day trips from Portland ).

  • Day 1: Arrive in Portland, drive to Hood River
  • Day 2: The Columbia River Gorge
  • Day 3: Hood River & Around
  • Day 4: Mount Hood
  • Day 5: Mount Hood
  • Day 6: Portland
  • Day 7: Portland & Fly Home

7 Days in Oregon: The Coast

Add a day if you want to do a day trip out to the mountains, and focus on Hood River or Mount Hood. 

  • Day 1: Arrive in Portland, drive to Astoria
  • Day 2: Astoria
  • Day 3: Cannon Beach & Around
  • Day 4: Tillamook & Three Capes Scenic Loop
  • Day 5: Drive to Portland

10 Days in Oregon

With 10 days, do a loop starting and ending in Portland that takes you first out to the mountains (and the Gorge), then head west out to the coast for a couple of nights before returning to Portland. 

  • Day 6: Drive to Cannon Beach
  • Day 7: Cannon Beach & Around
  • Day 8: Tillamook & Three Capes Scenic Loop
  • Day 9: Drive to Portland
  • Day 10: Portland & Fly Home

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Omg.. I cannot tell you how well written and amazing guide this is. Everything is broken down so well and easy to understand. Loved your blog and have already fallen in love with all the pictures of the falls and mountains you have on this blog. Thank you for writing this up.. Will surely use this guide when we plan to travel.

Thanks for the kind words, Kina!

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Home » North America » USA » Oregon

Epic Oregon Road Trip Travel Guide | Best Routes in 2024!

Going on a  road trip in Oregon  has to be one of the best ways to experience the state! With your own car and the freedom of the road, you’ll be able to go wherever you want and see whatever you like in this glorious state.

Oregon is a magical place full of beautiful landscapes, interesting people, and amazing food and drink. There are few other destinations in the world where you can surf and ski in the same day and, for that matter, drink some of the best beer of your life all the while.

There’s a lot to do in Oregon but, make no mistake, this is a big, wide-open state, one that requires plenty of time and patience to see.

Renting a car in a foreign state or country can be intimidating. Travelers may not know where to go or what to do. They may be worried about expenses or spending too much money pointlessly as well.

Don’t worry – we have the insider information you need for an EPIC Oregon road trip.

Written by a road-trip expert and local, this epic guide covers everything you need to know about visiting Oregon by car or campervan.

We’ll show you exactly how to stick to a budget, tell you about the best things in Oregon, and give you plenty of ideas and itineraries so you can easily plan out your entire trip!

So let’s start planning your dream Oregon road trip!

how to travel to oregon

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Oregon Road Trips Costs

Best road trip in oregon.

  • The Oregon Coast

The Cascades Itinerary

Eastern oregon road trip, the grand tour oregon itinerary, places to visit in oregon, oregon road trip tips, apartments and hotels in oregon, renting a car or campervan in oregon.

Oregon is about average when it comes to the costs of living, though it is quickly becoming one of the more expensive states. A road trip in Oregon can be affordable or it could be expensive – it all depends on how you want to do it.

We at The Broke Backpacker always try to go on affordable adventures and are always looking for ways to travel cheap ! Even if we are unable to travel for $10/day, as we do in our favorite countries, we can at least help you reduce the prices of an Oregon road trip.

The average daily budget for an Oregon road trip is between $150-$200 – this includes gas, a rental car, lodging, food, drink, and entry into certain attractions. Make note of this number but please do not let it discourage you – we’re going to show how to reduce it to a more budget-friendly amount soon.

Gas will undoubtedly be your largest expense while on a road trip in Oregon. It’s sometimes hard to predict how much gas you will use but it is almost always is more than you expect. Do not take this expense lightly and do you everything you can to limit it.

Other than gas, the costs associated with a road trip in Oregon really come down to how you want to travel, eat, sleep, and drink. These run gamut from driving in a cheap economy car to a gas-guzzling SUV and eating out in expensive restaurants to cooking your own food at a campground.

If you are mostly cooking for yourself, camping, and exploring Oregon’s wild places, you can reduce that cost in half. Traveling with at least one other person will also keep costs much lower.

Think about what you want to do on your Oregon road trip route and then set a budget.

Below is a breakdown of the average costs of a road trip in Oregon.

hidden waterfall marion falls oregon photography roaming ralph

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Average Costs of an Oregon Road Trip

Rental car :  $30-$100

RV rental :  $100-$300

Gallon of gas:  $3.23

Private AirBnB home:  $80

Hotel room:  $120

Hostel:  $25-$30

Campground:  $5-$15 (sometimes free!)

Sandwich:  $6-$9

Beer at a bar:  $5-$7

Coffee:  $2-$3

Bottle of Whiskey from market:  $20

Dinner for two:  $30-$50

  • The Oregon Coast – 4 days
  • The Cascades – 7 days
  • Eastern Oregon  – 10 days
  • The Grand Tour Oregon – 14 days

Below is a list of sample Oregon road trip routes. Varying from 5 to 14 days in length, they cover many of the top destinations in Oregon. Each itinerary provides day-by-day highlights, which are meant to give you some good Oregon road trip ideas.

how to travel to oregon

The USA is  blisteringly beautiful. It’s also blisteringly expensive! Visiting two national parks in day can run you $70+ in entry fees.

Orrrr… you kick those entry fees to the curb, buy an annual ‘America the Beautiful Pass’ for $79.99,  and get unlimited access to ALL 2000+ federally managed sites in the States totally FREE!

You do the math. 😉

The Oregon Coast is probably the most beloved road trip in the entire state and is a popular area for a holiday stay with both locals and out-of-towners. People flock here to get away from the rat race for a little while and tend to just laze about on the beach or in a local diner.

The Oregon Coast itself is not well-known for its warm weather or clear days, but rather its rugged beauty. Dramatic cliffs, tide pools, and sea stacks are the most notable landmarks here – palm trees are markedly absent.

The best part about a road trip on Oregon Highway 101 is that you’ll never be far away from the coast. This route hugs the near entirety of the shoreline and only deviates when passing through an epic forest. For 90% of the way, it’ll just be you and the ocean.

oregon road trip map itinerary 4 days

  • Bandon by the Sea
  • Samuel H Boardman Park
  • Ecola State Park
  • Cape Perpetua
  • Florence Sand Dunes
  • Pacific City Camping Resort Yurts
  • Windermere on the Beach  (Bandon)
  • Ecola Creek Lodge  (Cannon Beach)
  • Norblad Hotel  (Astoria)
  • McMenamins Gearhart Hotel  (Gearhart)
  • Shucking fresh oysters
  • Bonfires on the beach
  • Surfing at Oswald West
  • Whale watching

The entire way.

  • Pelican Brewery (Cape Kiwanda)
  • The Schooner (Netarts)
  • Fort George Brewery (Astoria)
  • Local Ocean Seafoods (Newport)
  • Mattie’s (Brooking)
  • Festival of the Dark Arts in Astoria (February)
  • Goonies Day in Astoria (June)
  • Newport Seafood and Wine Fest (February)
  • South Coast Clambake and Jazz Fest (March)
  • Southern Oregon Kite Festival (July)

ecola state park oregon coast road trip

Oregon’s Cascade Range is not the highest nor the most epic in the USA – these mountains are fairly gentle and draw attention only when there is a volcano around. Hidden in the lush fur of these slopes though are, hands-down, the best waterfalls in the country, not to mention some of the most beautiful lakes in the world. Better yet, some of Oregon’s best cabins and treehouses are found here, so book a stay amongst the forests for a once-in-a-lifetime experience!

Mt Hood and Crater Lake are the Cascade’s most famous landmarks and both are must see places in Oregon. In between these two are countless more treasures, including, but not limited to, Jefferson Park, Marion Falls, Clear Lake, and the Three Sisters Wilderness. I’m barely scratching the surface as well.

Following a road trip in the Cascades, you will also have the chance to drive up the Willamette Valley, which has some of the finest Pinot Noirs in the world. Nothing really beats a glass of wine or a B&B at a vineyard after spending a week in the mountains.

map of oregon travel itinerary

  • Crater Lake
  • Columbia River Gorge
  • Willamette Valley vineyards
  • Lots of waterfalls
  • Maverick Inn  (Klamath Falls)
  • Pacific Crest Trailhouse  (Cascade Locks)
  • Eugene Whitaker House
  • Bunk + Brews Historic Lucas House  (Bend)
  • Hiking/skiing at Mt Hood
  • Rock climbing at Smith Rock
  • Swimming at Crater Lake
  • Willamette Valley wine tours
  • Waterfall photography
  • Crater Lake Rim Road
  • Highway 138
  • Crux Fermentation Science (Bend)
  • Sam Bond’s Garage (Eugene)
  • Caspian Cafe (Eugene)
  • The Painted Lady (McMinnville)
  • Ritter’s Housemade Foods (Salem)
  • Oregon Country Fair (July)
  • International Pinot Noir Celebration (July)
  • Wooden Shoe Tulip Festival (April/March)
  • Tigard Festival of Balloons (June)
  • Bend Brew Festival (August)

If you need more recommendations on where to stay on your road trip, check out these cottages in Oregon .

crater lake in the summer oregon road trip

A new country, a new contract, a new piece of plastic – booooring. Instead, buy an eSIM!

An eSIM works just like an app: you buy it, you download it, and BOOM! You’re connected the minute you land. It’s that easy.

Is your phone eSIM ready? Read about how e-Sims work or click below to see one of the top eSIM providers on the market and  ditch the plastic .

A visit to Eastern Oregon will be a wholly unique experience compared to the Western portion of the state. Deciduous rainforests and beaches are swapped for desert-scapes and hazy mountains. If you wanted to see a side of Oregon that few are even aware, this is the one.

There are lots of things to do in Eastern Oregon. Smith Rock offers some of the best climbing in the country while the Wallowas (AKA the Oregon Alps) offer some of the best skiing and hiking in Colorado . Steens Mountain and the Alvord Desert are two of the greatest hidden gems on the West Coast and are known only to adventurous Oregonians.

The culture is also distinct from the rest of the state. Cowboys, whiskey guzzlers, social pariahs; all of these are the types of people you’ll see in Eastern Oregon.

map of oregon travel itinerary

  • Painted Hills
  • Steens Mountains
  • Hell’s Canyon
  • Dreamer’s Lodge  (John Day)
  • Eagle Cap Chalets  (Joseph)
  • Rory and Ryan Inn  (Burns)
  • Brewery tours in Bend
  • Snowboarding at Mt Bachelor
  • Hiking in Wallowas
  • Desert scenery
  • Cowboys in Pendleton
  • Steens Mountain Road
  • Scenic Lakes Byway
  • Deschutes Brewing (Bend)
  • McKay Cottage (Bend)
  • Roosters Country Kitchen (Pendleton)
  • Arrowhead Chocolates (Joseph)
  • Sisters Folk Festival (September)
  • Deschutes County Fair (August)
  • Pendleton Whiskey Music Fest (July)

steens mountain oregon

This the best road trip in Oregon – hands-down. Hell, this is one of the best drives in the USA ! You see everything and then some! The coast, the Cascades, the deserts of Eastern Oregon; all of these areas will be available to you with this itinerary.

In addition to the grand majority of the locations listed above, you will also have more time in Southern Oregon. This region is one of the most neglected parts of the state, which is unfair considering what it offers. The river rafting is epic, Ashland is one of the most charming cities you’ve never heard of, and the wine is arguably even better than that of the Willamette Valley.

So if you have time to kill and want to see the best of Oregon, look no further than this route. Oregon is beautiful and this is the best way to see it.

oregon road trip map itinerary 14 days

  • Eastern Oregon
  • Timberline Lodge
  • Traveler’s House  (Portland)
  • The Ashland Hostel
  • Columbia Hotel  (Ashland)
  • Everywhere else mentioned prior
  • Skiing at Mt Hood
  • Climbing at Smith Rock
  • Rafting in Southern Oregon
  • Chilling in Ashland
  • Wine and beer tours
  • Seafood on the coast
  • Hiking in the Wallowas
  • Growler’s Taproom (Portland)
  • Shalom Y’all (Portland)
  • Cartopia (Portland)
  • Brother’s Restaurant (Ashland)
  • Cafe Broder (Portland
  • Everything else mentioned in this guide
  • Ashland Shakespeare Festival (February)
  • Portland Brewer’s Festival (July)
  • Portland Rose Festival and Parade (May/June)
  • Portland Waterfront Blue’s Festival (July)
  • Pickathon (August)
  • Portland MFNW (August)

multnomah falls winter landscape oregon road trip

Below is a list of the best road trip stops in Oregon. Study them well and decide which ones you like the most.

Road Trip to Portland

The City of Roses. Little Beirut. Rip City. Bridgetown. Stumptown. Call it what you will but few names can actually capture the intangible flavor and uniqueness that Portland excludes in abundance.

For years, Portland was a city of obscurity, full of eccentrics and abject people. For residents, this anonymity was an ideal situation that allowed them to cultivate their weirdness. Portland has only been “discovered” in recent years by the rest of the world and has since developed into a full-on tourist destination.

Portland is not a big city by American standards. There are no large attractions in Portland like a Hollywood Sign or Liberty Bell. Life is simpler (and better) in Portland because people care mostly about good food, good beer, and good health (both physically and spiritually). For these reasons, the best things to do in Portland are to just eat, drink, and go for a walk.

portland oregon and mt hood at dusk from pittock mansion

The best districts in Portland to walk around are definitely the Alphabet District , the Pearl, Alberta Arts , Hawthorne , and Laurelhurst . Other neighborhoods like Belmont, Mississippi, Division, and Chinatown are also worth visiting. On either side of the Willamette River are the Eastbank Esplanade and Tom McCall Waterfront , which are both great places to wander around.

A hike through the lush Forest Park makes for a lovely day. Inside and on the outskirts of the large park are some of Portland’s best attractions like Pittock Mansion , the Rose Gardens , and Japanese Gardens .

If there were must-see landmarks in Portland then they’d probably the bridges. Portlandians are in love with their bridges and take great pride in them. St. John’s Bridge is a crowd favorite as is the iron Hawthorne Bridge.

I’d go into more detail on the city, and talk about the many restaurants and bars, but, unfortunately, there is not enough time and space available in this guide. That’s what the our Portland Budget Travel guide is for – blessings!

  And the  coolest places in Portland to go .

  Craft a killer  Portland travel itinerary .

  Read about the  coolest hostels in Portland .

  And book a killer  Airbnb Portland apartment .

Road Trip through the Columbia River Gorge

With endless outdoor opportunities, the much loved Columbia River Gorge is like a playground for adults! Those looking for the best hikes near Portland should head directly to this scenic area. Also, there are some excellent breweries nearby offering crucial post-hike beers.

Starting in Troutdale and driving along the  Historic Columbia River Highway , you’ll first arrive at the Portland Women’s Forum , which has one of the most iconic views of the Gorge. You’ll see the Vista House perched on the walls of the gorge in the distance as well as the Columbia River .

From there you can continue on to picturesque Laurotell Falls and Bridal Veil Falls (see if you can find the elusive Upper Bridal Veil Fall ). Nearby Angel’s Rest is a very popular sunset hike for locals as well.

columbia river gorge from womens forum viewpoint

The next stop is Multnomah Falls, which is arguably the most spectacular waterfall in Oregon. This near-perfect waterfall drops over 500 ft amidst verdant foliage and is one of the most photographed places in Oregon. In front of the falls is an equally photogenic bridge, which makes the scene look like Rivendell.

Beyond Multnomah Falls, you’ll pass by many other superlative portions of the Gorge, notably Oneonta Gorge and Eagle Creek . These are some of the most beautiful places in Oregon as well as the most crowded. Note that this part of the Gorge was damaged recently by a wildfire and that some trails may be closed.

Past Eagle Creek is Cascade Locks, home to the historical Bridge of the Gods, which is where the PCT crosses into Washington. Further along is the Hood River, which is one of the coolest towns in Oregon. Here are, hands-down, some of the best breweries in Oregon in addition to some killer windsurfing and gorgeous views of Mt Hood and Mt Adams.

Road Trip to Mt Hood

Oregon’s pride and joy, the image that most Oregonians can recall from their earliest memories, is Mt Hood. For outdoor enthusiasts and mountain lovers, Mt Hood will be the crowning achievement on their road trip in Oregon.

Getting to Mt Hood is very easy as one of the states main arteries ( Highway 26 ) runs literally right next to it. The drive is gorgeous and a little perilous if you’re visiting Mt Hood in the winter.

If your car is not able to drive in the snow, which is very common beyond December, you can still catch a local shuttle in Sandy to the main alpine settlements: Government Camp and Timberline , the latter of which is famous for appearing in Stanley Kubrik’s The Shining .

Along 26 are several stops that you should absolutely make time for. Trillium Lake and Mirror Lake are local favorites, however, it’s also one of the most famous hikes in the USA , so the trails can be quite crowded.

mt hood pink sunset trillium lake snow roaming ralph photography

There are several awesome spots on the eastern and northern flanks of Mt Hood that can be accessed by several forest roads. Cloud Cap , Tamanawas Falls , and Lost Lake are great places to check out.

If you’re a skier, then Mt Hood is unquestionably one of the best places in Oregon to visit in the winter. The skiing here is world-class and runs come in many forms, from tended to the backcountry. If you’re visiting Oregon in the summer, no worries; Timberline Lodge has the longest ski season in the country and is open 365 days a year.

Mt Hood is one of the most climbed glaciated mountains on the planet, second only to Mt Fuji. It is a great introductory peak for beginners and requires only a long day to summit. You will still need the proper adventure equipment to climb in as well as current condition reports.

Oregon Coast Road Trip

The Oregon Coast is not the typical kind of beach getaway – it’s not warm, it’s not very comfortable, and it’s not at all like those tropical postcards.

oRainy, rugged, and utterly romantic, the Oregon Coast is a marvel in its own way. If you’re travelling the USA for the adventure and appreciate a harsher beauty(or possibly like to wear both sandals and sweaters at the same time), you will instantly fall in love with this place.

The Coast is long and nearly 100% accessible via the Oregon Coast Highway 101 . A road trip on this highway will give you tons of opportunities to experience the local attractions. The Oregon Coast can roughly be divided into three parts (North, Central, and South) and between the three, there are, honestly, too many things to see and do.

oregon coast sunset at indian beach oregon coast road trip roaming ralph photography

Starting north you have the top weekend getaways for Portlandians – Astoria, Seaside, Cannon Beach, and Manzanita. Astoria is mostly famous for being the setting for Steven Spielberg’s The Goonies.

Seaside is a cute town popular with families and is a bit touristy. Cannon Beach is equally as touristy but hosts the stunning Haystack Rock.

Manzanita is the most laidback of the bunch and is aw great base for day trips to Oswald West State Park and Neahkahnie Mountain , both of which offer some of the best Oregon Coast hikes.

Moving south we head past Tillamook , the cheese capital of Oregon, and past Cape Kiwanda, one of my favorite places in Oregon, before arriving in Newport , famous for the highly-regarded Oregon Coast Aquarium . Beyond Newport is ultra-rugged Cape Perpetua , home to the Devil’s Churn, Thor’s Well, and Sea Lion Caves.

After Perpetua, we drive to Florence and the epic Oregon Sand Dunes , which originally inspired Frank Herbert to write the sci-fi masterpiece, Dune . Quad biking on the dunes is one of the most popular things to do on the Oregon Coast, though there are plenty of other places to go for a nice walk.

Saving the best for last, we wrap our Oregon Coast road trip in the south. The stretch between Bandon and Brookings is superlative with state parks like Face Rock, Samuel H. Boardman, and Pistol River all providing amazing settings. Some of the best hikes on the Oregon Coast are also around Boardman.

Willamette Valley Road Trip

The Willamette Valley is the breadbasket of Oregon and the source of much of its delicious produce. It also hosts some of the most respected wineries in the USA, which produce some of the finest Pinots in the entire world, not to mention a number of interesting towns and natural attractions.

The Willamette Valley runs for about 150 miles from Portland south to Eugene . The largest highway in Oregon, Interstate 5 , runs through the Willamette Valley meaning you can travel by car to California .

I5 itself doesn’t really have a lot of great views and the drive itself is pretty boring. Deviate slightly from I5 and there’s lots more though.

There are over 500 wineries spread throughout the Willamette Valley. The greatest concentration of wineries is around Highway 18 near McMinnville, Salem, and Newberg . You could easily spend an entire day touring these vineyards and trying some of the best wine in the country but please remember to drive safely.

willamette valley winery and countryside oregon road trip

To the west of the Willamette Valley, you’ll the see the Cascade Range rising. The Cascades, running all the way from Washington to California, are like the geographic spine of the state and heavily influence the weather.

Hidden inside of the Cascades are some more great waterfalls, which make for great day hikes close to Portland.

Silver Falls State Park is one of the most popular places to visit in Oregon because it offers great scenery and easy trails. Nearby is the much more intimate albeit difficult Abiqua Falls , which has become a local favorite.

Penetrate even deeper into the Cascades and you’ll find hidden gems like Olallie Lake, Bagby Hot Springs, Jefferson Park, Marion Falls, and Three Fingered Jack.

Eugene is worth dropping by if you have a moment. Eugene was once considered the “hippie capital” of Oregon though it’s more gentrified now. You can still get a taste of the counterculture in the bluesy Whitaker District.

Road Trip to Bend

Located on the other side of the Cascades in the High Oregon Desert, Bend is, in a lot of ways, like a foil to Portland. Bend is smaller, more rural, more politically conservative, and even more laid back than “big city” Portland.

Bend still has that quintessential Oregon charm though and ultimately makes for an awesome stop on any Oregon road trip route.

You’ll have to cross the Cascades in order to arrive in Bend. You can cross the Cascades via several passes and each offers their own set of attractions. I personally enjoy driving along Highway 20/126 because I have a chance to visit some of my favorite places in Oregon including Koosah Falls, Clear Lake, Tamolitch Falls, Proxy Falls, and Linton Falls . Note that only the larger highways like 26 may be open in winter.

Bend mostly gets attention for the surrounding landscape, which you’ll be introduced to on the drive in. The city itself is really cool though and actually a really fun place in Oregon to hang in, so it’s definitely worth staying in Bend for a couple nights. If you need ideas for places to stay in Bend, consider checking out one of the incredible vacation rentals . The local breweries, like Deschutes and Crux , are some of the finest in the state and the food ain’t bad either.

People usually head outdoors immediately upon arriving in Bend. Around the city are some of the best mountain biking, skiing, climbing, and hiking in Oregon, making the area a paradise for outdoors people.

smith rock near end oregon road trip roaming ralph photography

Nearby Mt Bachelor is one of the best places to visit in Oregon in winter as the snow is legendary. North of Bend is the holy Smith Rock , which is often considered the birthplace of American rock climbing. East is endless sagebrush.

I definitely suggest driving on the Cascades Lakes Byway in the summer. You can visit local favorites like Tumalo Falls and Sparks Lake , all the while being afforded views of the Three Sisters . South Sister is a popular and relatively easy climb.

Road Trip to Crater Lake

Oregon only has one national park but it is easily one of the most stunning parks in the USA . Crater Lake is a marvel, an enormous body of water held high in the air on top of a collapsed volcano. The water is one of the deepest shades of blue that you will ever see and, officially, some of the clearest. There’s simply nothing else like it in the world.

Crater Lake is located a couple hours south of Bend in the Cascade Mountains. There are several entrances to the park but only one, Munson Valley via Highway 62 , is open (sometimes) in the winter. You’ll have to pay to enter the park though rates change depending on the time of year (summer: $25 winter: $15).

There is a lot to do at Crater Lake, though most people just stand there and stare in awe at it. You can hike, climb to one of the many surrounding peaks, descend down to the lake’s edge for a very cold swim, or simply drive around the rim in the summer on the Rim Road.

crater lake sunset roaming ralph photography

Several times in the year the road is closed to vehicular traffic so that bikers and pedestrians may enjoy the park without being disturbed, which is a really nice touch.

Though there is more to do in the summer, the best time of year to visit Crater Lake is in the winter. During this time, there are very few people, tons of snow, and just a powerful stillness to the place. The silence in the winter is almost total and you’ll be shocked, maybe even scared at how serene it is.

You can, of course, camp at Crater Lake though campgrounds can fill really quick. If you strike out camping, the nearest large town is Klamath Falls and it has plenty of lodging.

An Eastern Oregon road trip is a must for anyone who wants to get the full Oregonian experience. Some of the USA’s most beautiful places are found in this part of the state and anyone interested in a more rugged adventure will enjoy Eastern Oregon very much.

A lot of people often imagine Oregon covered in trees and being rained on 24/7; few realize that almost two-thirds of the state is actually a mix of desert terrain and stark mountains.

Lying on the other side of the Cascades, Eastern Oregon is, contrary to the common image, arid, hot, and sometimes bitterly cold. This austere landscape is gorgeous though and only solidifies Oregon as one of the most geographically diverse states in the USA.

painted hills viewpoint sunset oregon road trip roaming ralph photography

The most popular place in Eastern Oregon is probably the kaleidoscopic Painted Hills , located in the John Day Fossil Beds . These hills are a geologic wonder and famous for their bright colors.

Surrounding the John Day area are the Ochoco, Malheur, and Umatilla forests as well as the Blue Mountains and Strawberry Mountains . Fun fact: the Blue Mountains are home to the world’s largest organism – a 2400-year-old fungus that covers over 2,000 acres.

In the far northeastern corner of the state are the Wallowa Mountains aka “The Alps of Oregon.” The Wallowas are an outdoor wonderland that offer great skiing opportunities and some of the best hikes in Oregon.

Most of the Wallowa Mountains fall within the Eagle Cap Wilderness though local townships like Joseph and Enterprise are worth visiting as well.

Nearby to the Wallowas is the historically significant Snake River and Hell’s Canyon , the deepest canyon in the entire United States.

There are many more hidden parts in Eastern Oregon that are really out in the middle of nowhere. To learn more about some of these remote locations among others, refer to the section below where we talk about secret Oregon.

how to travel to oregon

Wanna know how to pack like a pro? Well for a start you need the right gear….

These are packing cubes for the globetrotters and compression sacks for the  real adventurers – these babies are a traveller’s best kept secret. They organise yo’ packing and minimise volume too so you can pack MORE.

Or, y’know… you can stick to just chucking it all in your backpack…

Off The Beaten Path Oregon Road Trip Ideas

Oregon has so many hidden treasures for you to discover! To see something different, start with these relatively unknown locations, which are among the most uniques places to visit in Oregon.

1. Steens Mountains

The epitome of off-the-beaten-path in Oregon; these mountains are located in the far southeastern corner of the state and it takes a real journey to get here. Drive to the top of the mountains via the astounding Steens Mountain Road .

Be on the lookout for wild horses and, in the autumn, the golden aspens. On the other side of the Steens is the Alvord Desert – a surreal playa that is popular among both artists and off-roaders who like to go for joy rides.

2. Owyhee Canyonlands

One of the last untouched desert frontiers in America, full of hoodoos, stone towers, and delicate ravines. The Owyhee Canyonlands are often compared to the national parks and landscapes of Utah  albeit not as extensive.

Popular among hikers, rock climbers, and river rafters though not many people actually make it out this far due to rough and remote roads. Definitely one of the most beautiful and unique places to visit in Oregon.

3. Southern Oregon Road Trip

Though not exactly hidden, Southern Oregon often receives far less attention than the rest of the state. People usually visit to attend the famous Shakespeare Festival in charming Ashland or when passing through on a road trip from California, but there is a lot more happening than most are aware of.

The Rogue Valley has a burgeoning wine and beer scene that will soon rival the Willamette Valley. In terms of natural attractions, there is the Rogue River with its world-class rapids as well as the rugged Siskiyou Mountains and Oregon Caves , all of which make for great adventures.

lounging in the alvord desert with an umbrella eastern oregon road trip

Oregon Roadside Attractions

Americans have a weird affinity to the strange landmarks that are usually found out in the middle of nowhere. The roadside attractions in Oregon have become so admired that many people go on a trip just see them!

Below is a list of some of the most interesting roadside attractions in Oregon. Did we mention that a lot of these stops are among the best cheap things to do in Oregon as well?

  • Peace Candle of the World (Scappoose) – A former silo that was filled with wax and painted red to resemble a giant candle. Promotes world peace.
  • Enchanted Forest (Salem) – An amusement park filled with fairytale-themed rides and attractions. Whimsical and a little creepy.
  • The Oregon Vortex (Gold Hill) – Place where the laws of physics are purportedly non-existent due to paranormal activity.
  • Short Bridge Ghost Town (Short Bridge) – A seemingly derelict town that is actually a very well designed prop.
  • Octopus Tree (Tillamook) – An old spruce tree that came to be shaped like an octopus by unknown means.
  • Prehistoric Gardens (Port Orford) – A series of lifesize dinosaur recreations in the coastal rainforest. Intended to look like a prehistoric zoo.
  • Peterson Rock Garden (Redmond) – An estate full intricate statues and structures made from rocks and stones.
  • Oregon Corndog (Rockaway Beach) – Home to the world’s largest (artificial) corn dog. There’s also a bucking mechanical corn dog ride complete with a saddle.
  • Evergreen Aviation and Space Museum (McMinnville) – Holy ground for anyone interest in aviation. Hosts a large collection of planes, most importantly the Spruce Goose, one of the largest planes ever designed.
  • Oregon State Hospital Museum of Mental Health (Salem) – A real mental institution that was used for filming One Flew Over the Cuckoo’s Nest. Now displays important artifacts from the movie as well as archaic therapeutic techniques.

octopus tree oregon roadside attraction

Oregon Scenic Drives

Everywhere you look in Oregon, there’s beauty; much of it can be seen from the seat of your car! Those who want a glimpse of the state’s splendor from behind the wheel should definitely check out these scenic drives in Oregon.

  • Highway 101 – A road trip on Oregon Highway 101 is a great way to experience the best of the Oregon Coast. Most of the Oregon coast’s top attractions are within a stone’s throw from the highway as well. Highlights include the views from the slope of Neahkahnie Mountain, driving past the Oregon Dunes , and seeing the sea stacks of Bandon and/or Cannon Beach . This highway also makes for a natural transition when road tripping from California as the 101 runs all the way up the West Coast to Washington .
  • Interstate 84 – Drive through one of Oregon’s greatest points of pride: the Columbia River Gorge. With high walls and dense woods, the Gorge is like something out of Scandinavia. Aside from being gorgeous by itself, the Gorge has lots of hiking opportunities as well as some of the best waterfalls in Oregon.
  • Highway 138 – One of my favorite scenic drives in Oregon. Depart from Crater Lake and head northwest through the Cascade Range. Along the way, you’ll have the opportunity to visit some of the prettiest and most unique places in Oregon, including Mt. Thielsen (aka the Lightning Bolt) and Toketee Falls . 138 eventually enters the Umpqua River Valley, which is equally remarkable.
  • Highway 26 – A great commute that affords road trippers glimpses of the tableau that is the Oregonian landscape. On this scenic drive through Oregon, you’ll have the chance to experience the state’s amazing geographic diversity. Start on the coast (Cannon Beach) and drive east through the city of Portland, the alpine forests at the base of Mt. Hood, and then down to the Oregon High Desert. 26 goes all the way to Boise, Idaho but the Painted Hills are a great place to stop.

rowena crest road trip oregon

Why Visit this Part of the World

Oregon is one of the brightest and quirkiest places in all of the USA. It is a spectacular state that provides everything that makes for an awesome road trip: great food, gorgeous natural attractions, engaging people, and best of all, an easygoing culture that loves to enjoy itself.

Due to its relative isolation, Oregon has always been a hideaway for the abject in society, which has shaped both its history and demographgics for better or worse .

In short, many people – the eccentric, unaccepted, burnt-out, adventurous sorts – who felt confined in conventional American life all fled to the farthest corner of the US, that is the Pacific Northwest . The result of this migration is now an established culture that champions the strange and alternative.

portland oregon old town sign

Oregonians are very proud of their eccentricities. You’ll often see people in the cities of Portland and Eugene doing, saying, and wearing whatever they want, sometimes to a bombastic level.

Libertarianism and separatism are very popular concepts in Oregon, both among urban and rural centers. Regardless of politics though, Oregonians are very outspoken people.

And why shouldn’t they be outspoken? Oregon has some of the most fantastic landscapes in the USA, a mostly forward-thinking society, and a people that really give a shit. Quality, ecologically-friendly products are of the utmost importance here and social progressivism is often at the forefront of people’s lives here.

There are very few places as interesting or as enthralling as Oregon. Between the hugely varied landscapes and the larger-than-life personalities, this is a state that grips you and doesn’t let go. It plants a seed and takes root in everyone’s mind and everyone has a hard time ending an Oregon road trip.

Getting Insured

Traveling without insurance would be risky so do consider getting good backpacker insurance sorted before you head off on an adventure.

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

how to travel to oregon

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

Top Tips for Broke Backpackers

Below is a list of Oregon road trip ideas for saving money. Try and practice these as much as possible.

  • Rent an economy car: Prices can be as low as $25/day depending on the time of year and how far in advance you reserve. Economy cars are also more fuel efficient so you’ll save on fuel. Use apps like ViaMichelin to find cheap gas, which, seriously, always ends up being one of the most surprising and costly expenses on a road trip.
  • Use vehicle relocation services: These brilliant services offer huge discounts to people on the condition they get a vehicle to a certain place at a certain time. No joke, you can rent a car sometimes for as low as $1/day! Availability is very limited though, so keep a watchful eye on the sites. Check immova and Cruise America to start with.
  • Sleep overnight in an empty lot: Though not technically legal in Oregon, people sleep in parking lots all the time. Make sure the lot is safe by asking around. Walmarts are reportedly good places to park overnight as they allow overnight parking.
  • Camp: Unless you want to fork out big bucks for a lodge, pack the car with your camping essentials . Campgrounds are way less expensive and sometimes even free.
  • Cook your own food: Eating out can be very expensive in Oregon. Cook your own food as much as possible to save – I recommend bringing a portable backpacking stove. Otherwise, have a fancy night out at a food cart.
  • Do free shit: There are lots of free things to do in Oregon! From hiking to laying on the beach to going to the local monuments; all of these things cost you nill. You can get started with this awesome guide to free activities in Portland from OregonLive. Be sure to keep your ear to the ground for all things free in Oregon.
  • Pack a travel water bottle: It’s good for your wallet and the environment.

people playing on the oregon coast roaming ralph photography

Sometimes you need a roof over your head and your own shower to clean all that grime away from camping. Luckily, there are a whole range of accommodation types in Oregon catered to all sorts of travelers.

It might be a good road trip idea in Oregon to stay at a lodge once or twice for a recharge. Sticking to a budget while not staying in a dump will still require a bit of research.

There are plenty of budget hotels and motels in Oregon but they suffer from a drab and uninspired design that is endemic to most cheap American lodging.

portland oregon at night city lights

You can check into a cheap hotel in Oregon for a night, and will often have to, but don’t expect much. At more than $60/night minimum, staying in these cheap hotels can start to feel like a waste very quickly.

Although the USA’s hostel scene is lacking outside the major backpacking destinations, you can find hostels in Oregon that are affordable and fun.

AirBnBs in Oregon are often cheaper and far more intimate than generic hotels. There are some really crazy AirBnB rentals out there as well! I’ve seen yurts, teepees, tree houses, renovated barn houses, and much more listed for rent in Oregon.

These would certainly be among the best places to stay in Oregon when visiting.

To save the most money on your road trip through Oregon, consider sticking to hostels and campgrounds. Hostels in Oregon are quirky and full of character not to mention the most affordable form of accommodation.

If you’re feeling lucky, you could also try your hand at finding a host with Couchsurfing! Lots of people use this though so competition is quite high in Oregon.

Best Places to Stay in Oregon on a Budget

Camping in oregon.

Camping is absolutely one of the best ways to sleep on a road trip through Oregon because

  • It’s cheap and…

There’s nothing better than a night outdoors with a car full of goodies, a roaring fire, and a good pint of camp whiskey. Americans love it, Oregonians especially love it, and so should you!

There are campgrounds everywhere in Oregon and in all sorts of varieties. There are standard sites, primitive sites, RV parks, glamping, something called “treetop camping” and many, many more types that just get more and more ridiculous. You can even stay the night in a fire lookout , which has to be one of the coolest places to stay in Oregon.

camping on an oregon road trip

You can use this search engine to find a campground in Oregon . Be sure to keep your eye an AirBnB as well – there are lots of interesting private camps listed.

Campgrounds in Oregon offer a range of amenities and at a range of prices. Most facilities will require a small fee to be paid, which goes toward keeping the grounds tidy and clean.

You can sometimes pay online but most of the time there will be a form at the actual site that you need complete on your own. Even though registrations from these are not always checked, please be respectful and pay the nominal fee for your stay.

If you intend on staying at a campground near of the more famous attractions in Oregon, like the Painted Hills, Smith Rock or Crater Lake, then you definitely consider reserving a space ahead, especially in the summer months. Campsites can fill up very quickly in Oregon.

If there appears to be no space leftover at your prospective campsite, there may still be walk-up sites available. Get to the grounds as early as possible to snag these spaces.

Camping in Oregon – Gear Checklist

Camping is one of the best ways to experience the USA, and Oregon has some of the finest camping in the whole country. You could sleep in your car or an RV while road tripping in Oregon, but sleeping outside under the stars is way more fun.

Having a good-quality camping tent  will keep you comfortable on those chilly nights and give you lots of flexibility when it comes to finding a place to sleep.

Here are some other essentials that we recommend if you plan on camping out…

Pacsafe belt

Travel Security Belt

This is a regular looking belt with a concealed pocket on the inside – you can hide up to twenty notes inside and wear it through airport scanners without it setting them off.

sea to summit towel

Microfiber Towel

Hostel towels are scummy and take forever to dry. Microfibre towels dry quickly, are compact, lightweight, and can be used as a blanket or yoga mat if need be.

Gifts for backpackers

Petzl Actik Core Headlamp

A decent head torch could save your life. If you want to explore caves, unlit temples, or simply find your way to the bathroom during a blackout, a headtorch is a must.


‘Monopoly Deal’

Forget about Poker! Monopoly Deal is the single best travel card game that we have ever played. Works with 2-5 players and guarantees happy days.

Mesh Laundry Bag Nomatic

Hanging Laundry Bag

Trust us, this is an absolute game changer. Super compact, a hanging mesh laundry bag stops your dirty clothes from stinking, you don’t know how much you need one of these… so just get it, thank us later.

For plenty more inspiration on what to pack, check out my full road trip packing list .

backpacker drinking using grayl geopress filter bottle

Drink water from ANYWHERE. The Grayl Geopress is the worlds leading filtered water bottle protecting you from all manner of waterborne nasties.

Single-use plastic bottles are a MASSIVE threat to marine life. Be a part of the solution and travel with a filter water bottle. Save money and the environment!

We’ve tested the Geopress  rigorously  from the icy heights of Pakistan to the tropical jungles of Bali, and can confirm: it’s the best water bottle you’ll ever buy!

Free Camping in Oregon

Those on a road trip in Oregon should totally take advantage of the many free campgrounds spread throughout the state. Note that electricity, bathrooms, and running water are not guaranteed at any of these. Also be aware that many free campgrounds in Oregon may require a 4×4 vehicle to reach.

Refer below for a list of some of our favorite free campgrounds in Oregon or this website for a complete archive of free campgrounds.

mt jefferson eastern oregon as seen from lookout mountain roaming ralph

Books to Read during your Oregon Road Trip

These are some of my favorite travel reads and books set in Oregon. Read one or two and you may have some great road trips ideas for Oregon…

  • One Flew Over the Cuckoo’s Nest – One of Ken Kesey’s most famous novels, thanks in part to the film of the same name. Paints a picture of mental health and conformity through the lens of a man who’s just too full of life.
  • Sometimes a Great Notion – Ken Kesey is a literary demigod in Oregon and this is arguably his greatest novel. A tale of a hardheaded logging family that goes on strike, leading the town to drama and tragedy.
  • The River Why – A quintessential American coming-of-age tale, both for the protagonist and the nation the book represents. Set in Portland and the Oregon Coastal Range.
  • Night Dogs – Vietnam War vet deals with violence in the streets and in himself. An excellent if not authentic crime novel.
  • The Lathe of Heaven – A man wakes up one day to discover that his dreams can affect reality itself. A novel exploring human creation and destruction. Set in Portland, which was the ultimate home of the author, sci-fi legend Ursula K Guin.
  • Dies the Fire – All electronics are rendered useless by a magnetic storm, resulting in humanity’s return to the Dark Ages. Brutality, desperation, and sword fights in Portland follow.
  • Lonely Planet: Washington, Oregon, and the Pacific Northwest – It’s sometimes worth traveling with a guidebook.

Renting a car is the most popular way of getting around Oregon. There are a myriad of car rental agencies here that offer varying deals and varying models.

To find the best rental car deal in the USA, use search engines that compare the prices from individual companies. We personally like using rentalcars.com as they’ve never failed to give us a great price.

You can also rent an RV or campervan and travel by way of vanlife , which means you don’t have to worry about packing camping gear. You will have to empty and refill the various wascampete and water tanks though, which will require a visit to the proper facilities. RVs also cost more to rent, use more gas, and demand higher prices at campgrounds.

Make sure you also purchase a RentalCover.com policy to cover your rental vehicle against any common damages such as tires, windscreens, theft, and more at a fraction of the price you would pay at the rental desk.

renting an rv in oregon roads

We suggest booking a campervan with Outdoorsy as they usually have a good selection and good prices. Better yet, Broke Backpackers also get a $40 discount with Outdoorsy! Just use the coupon code “BACKPACKER” when checking out.

The roads in Oregon are generally very good and a sedan or economy car should deliver you to most of Oregon’s top destinations. Only in the most remote portions of the state and the Cascades, will the roads be so bad that you need 4×4 or at least high clearance.

If you’re on a road trip in Oregon during the winter and want to go to the mountains, you will definitely need all-wheel or 4-wheel drive.

Tips for Saving Money on Car Rentals in the US

  • We mentioned before that you can reach out to vehicle relocation services, like immova and Cruise America , as a way of saving heaps of cash on rentals. Pursue these as best you can as they can save you a lot of money. Don’t get your hopes up too much though, as availability is always limited.
  • Car insurance isn’t always mandatory in the USA but is highly encouraged. This being said, you don’t necessarily have to buy car insurance from the company you’re renting from. Purchase a RentalCover.com policy to cover your vehicle against any common damages such as tires, windscreens, theft, and more at a fraction of the price you would pay at the rental desk.
  • Many credit card companies offer free car insurance if you book the car with the proper card. Call your credit card company for more information regarding terms and conditions.

oregon scenic drive in winter

Best Time to Visit Oregon

The best time to visit Oregon really depends on what you want to do. With lots of activities year round, you could go on a road trip in Oregon and always have something to do. Drinking beer is, of course, something that happens 365 days of the year.

There are several different climates in Oregon. Generally speaking, everything west of the Cascade Mountains is maritime e.g. there’s a lot more rain and mild temperatures. East of the Cascades is much drier and prone to extreme temperature shifts, which is a characteristic of the high desert.

Precipitation occurs almost always in the winter months regardless of location.

  • Summer is a great time to visit Oregon because the skies are almost always clear and rainfall is sporadic. There are lots of festivals during this time of the year and most Oregonians spend their free time outdoors. What little rain does fall in the summer is usually the result of occasional storms, which sometimes come in the form of thunderstorms. Thunderstorms often cause forest fires, which have become more common in recent years due to increasing summer temperatures and decreasing rainfall.
  • Spring and autumn are lovely seasons to visit Oregon but are somewhat brief. Summer usually goes into September and winter often feels very long (November-March).
  • Winters in Western Oregon are notoriously dreary as rain falls almost every day and the skies are almost always overcast. Being the tortured souls that they are, Oregonians love to be homebodies and stay warm with a beer at this time.

Luckily, the Cascades and parts of Eastern Oregon receive plenty of snowfall in the winter, giving winter athletes plenty of opportunities. In fact, Oregon has some of the best slopes on the West Coast.

portland oregon with rare snow oregon road trip roaming ralph photography

Things go wrong on the road ALL THE TIME. Be prepared for what life throws at you.

Buy an AMK Travel Medical Kit before you head out on your next adventure – don’t be daft!

Food in Oregon

Oregon is often ranked as one of the top foodie states in the country by several major publications; more often than naught, it’s #1. Thanks to a thriving farm-to-table scene and a population with a real culinary passion, Oregon has, seriously, some of the best food that you’ll ever eat.

Nearly every part of Oregon offers some amazing local product. To the east is grade-A cattle; to the west are the sublime bounties of the sea; and in the middle is the Willamette Valley, a hugely prosperous agricultural area.

When on a road trip in Oregon, there are so many ways to satiate your appetite. You can visit one of the many authentic farmers’ markets, swing by a roadside diner, book a table at a eclectic restaurant or eat at a food cart.

For those on a budget road trip in Oregon, I highly recommend eating at the small hole-in-the-wall joints and food trucks to save to money.

food carts in portland oregon sunny day

Hands down, the best food is found at the many food carts , for which Oregon is famous for. The food here is affordable, inventive, sometimes revolutionary, and always delicious.

Food carts are often labors of love, which means the food is extraordinarily cared for. If given the choice, I will always choose a food cart over a restaurant.

Like the anonymous food carts, the mom-and-pop restaurants found in bumfuck nowhere are also among the best things in Oregon. Simple as they may be in offerings, the ambiance and loving meals they provide are one of a kind.

I can think of many places that are so good they warrant road trips themselves. The gigantic burgers of Helvetia Tavern or the soothing ice cream of K & R Drive In are certainly worthy, if not sweet memories for me.

Get your Buzz On

Whether it’s because of the demand for alcohol during those depressing winter months or because the region produces some of the finest hops, grapes, and other botanicals for making beverages, makes no difference; Oregon loves to produce and consume booze in all of its forms.

Oregon makes some of the best wine, beer, and spirits in the USA and that is a fact that locals will defend with a fiery passion. (Go Pinot Noir, not California Cab.)

Agricultural epicenters like Hood River, the Willamette Valley, McMinnville, and Medford consistently produce the best booze in the state. Amongst these regions are dozens if not hundreds of wineries, distilleries, and breweries that offer countless alcoholic varieties.

Throw in the fact that many of these sites are located in gorgeous, bucolic settings and you have some of the most fun places to stay in Oregon.

If you had to choose one place to sample local wares or go party for that matter, it’d definitely be Portland. You cannot throw a rock in this city and not hit a bar; they’re simply everywhere.

taps in a growler refill store oregon beers

Nearly every type of bar as well: dives, speakeasies, country haunts, beer halls, urban wineries, clubs, and many more. Strip clubs are particularly well represented in Portland, so much so that the city actually has the highest concentration per capita in the country beating out both Orlando and Las Vegas.

No piece about getting buzzed in Oregon would be complete without talking about the marijuana, which is 100% legal in the state. Like alcohol consumption, you must simply be over a certain age (21) and only smoke it in certain places like on your property or away from businesses. You can buy weed a local dispensary , which only requires you to bring an ID and cash.

Being a Responsible Backpacker in Oregon

Remember to be a respectful camper while on your Oregon road trip. Depart from the grounds at a decent hour, follow leave no trace principles, and be very, very aware of fire bans. Forest fires are an enormous problem in Oregon and are often caused by reckless campers.

Oregonians are also very conscious of the environment and like to take care of it, as should you.

Reduce your plastic footprint: Perhaps the best thing you can do for our planet is to make sure you do NOT add to the plastic problem all over the world. Don’t buy one-use water bottles, the plastic ends up in a landfill or in the ocean.

I know it can be hard, but do your best to use the least amount of plastic water bottles that you can. Refill the ones that you do buy! Use a Grayl Geopress . Refill at your hostel/guest house! There are plenty of ways to reduce plastic!!!

Pack a  tough and cool travel water bottle . You’ll use it every single day whether you are traveling or not! Help save the planet, and pick up a water bottle here.

Check out our post on how to be a responsible backpacker.

forest fire in oregon

Make Money Online Whilst Traveling in Oregon

Want to stay in the USA longer? Worried that you don’t have enough cash for a longer Oregon road trip? One idea is to make money while traveling!

Teaching English online is a great way to earn a consistent income—from anywhere in the world with a good internet connection. Depending on your qualifications (or your motivation to obtain qualifications like a TEFL certificate) you can teach English remotely from your laptop, save some cash for your next adventure, and make a positive impact on the world by improving another person’s language skills!

It’s a win-win! Check out this detailed article for everything you need to know to start  teaching English online .

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sunset over mt jefferson from timberline lodge oregon roaming ralph

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I came upon this site searching for travel points,budgeting, anything Oregon and you hit it right on the button. This is the best well written and organized site I’ve read. I bookmarked it. Thank you so much.

Stumbled upon your awesome Oregon site while looking for things to see here in the great state of Oregon when the COVID-19 quarantine is lifted. I’ve only lived here for four years, but have been coming here all my life to visit family, so I’m familiar with a lot of the state. Thank you for such a comprehensive and thorough site about travel in Oregon.

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The Perfect Oregon Road Trip Itinerary – 7 or 10 days

Last updated on June 9th, 2024 at 12:35 pm

Oregon (pronounced “Ore-gun”, not “Ore-gone”!) is often overshadowed by its extremely popular neighboring state of California in the US. But if you are looking for a road less traveled then you have to take an Oregon road trip. In this blog post, we will share our detailed itinerary including what to see, do, and where to stay.

Below is a map of the route we took on this trip, click here to go to Google Maps. We drove across the state in a clockwise direction but you can do the same in an anti-clockwise direction as well. If you remember we did a similar 7-day road trip in Iceland and trust me when I say that our Oregon road trip was just as adventurous. Don’t forget to check out our post on waterfalls near Portland for more incredible inspiration.

FUN FACT: Oregon is the only other state in the US after New Jersey to have assistants at gas stations to fill gas in your car.

How Many Days Do You Need for an Oregon Road Trip?

We were able to make this a total of the 10-day trip including travel time. If you follow our Oregon itinerary you will have plenty of time to go on hikes, take wine tours, and relax on this road trip.

You can easily make this a 7-day road trip and we’ll tell you how in the modified itinerary below. However, if you have less than 7-days then I suggest visiting only Portland, Columbia River Gorge, Mt. Hood region, & Cannon Beach from the itinerary below.

Disclaimer: This post contains affiliate links.

how to travel to oregon

Related Read: SF to LA – An ultimate west coast road trip guide

Starting point 

We flew into Portland and spend 2 days in the city before starting our road trip. TIP: You do not need a car in Portland city so save yourselves some cash by renting a car the day you hit the road.

Portland would be our recommendation as a starting point for all those who are flying into Oregon. For those who are driving from the South i.e. California, the best starting point for you would be either the coast or Crater lake in this loop.

Oregon Road Trip Itinerary

Below is our detailed itinerary is broken out by each day. If you want to do a 7-day road trip then we have listed where it makes the most sense to skip things.

Day 1 & 2 – Portland

After you land in Portland spend 2 days in this funky city. We not only explored the city landmarks but in reality spend the entire weekend food binging in Portland. TIP: If you want to make this a 7-day road trip then spend just 1 day in Portland.

We will be writing a separate post on what to do on a weekend in Portland. But to highlight a few things –

  • Eat your heart out in the food capital on the west coast. From food trucks to delicious worldwide cuisines all around town you’re going to return with some additional baggage on your body.
  • Check out the largest bookstore in the world – Powell’s Bookstore
  • Must eat doughnuts (try both Bluestar & Vodoo doughnuts to give your own verdict no matter what the locals say)
  • Take a walking city tour or a Segway tour to learn more about the city
  • Check out the Japanese Garden

ACCOMMODATION: It usually nice if you stay in either downtown or the pearl district so you’re walking distance away from all the things –

  • Hilton Portland Downtown or the Hampton Inn Pearl District
  • The Bidwell Marriott Portland or the Courtyard Marriott City Center

More Places to Stay in Portland, Oregon

Harlow Hotel

Inn at Northrup Station

aerial view of Portland city in Oregon

Day 3 – Columbia River Gorge Waterfalls & wineries

Fasten your seatbelts and drive to the Columbia River Gorge which is only 30 minutes away from Portland. If you start driving early in the morning, you’ll easily be able to cover all the stopovers mentioned below in that order. For more details, read our in-depth blog post on Columbia Gorge road trip .

  • Portland Women’s Forum vista point (has the best sunrise view if there are no wildfire smoke)
  • Latourell Falls (add a short 2.4 mile hike here)
  • Multnomah Falls
  • Bridal Veil Falls (add a short 1.2 mile hike here)
  • Starvation Creek Falls
  • Wineries tour in Mt. Hood/Gorge

ACCOMMODATION: Spend the night in White Salmon, WA or Hood River, OR

Find fun things to do in Oregon during your road trip!

Panoramic view of columbia river gorge from Portland Women's Forum

Day 4 – Explore Mt. Hood Region

We spent 2 nights in Mt. Hood region which gave us the time to not only explore but also relax in the most gorgeous setting. There are a ton of outdoor activities to do here so spending only 1 day would be an injustice to this region. We have broken down the activities by each day for you –

  • Explore Hood River town which is known as the world’s kite surfing capital, perhaps indulge in some water activity or grab lunch here
  • The Gorge White House makes for a great stop for Apple cider tasting and fresh fruit & flower farm
  • If you happen to visit in spring don’t forget to check out the “ fruit loop ” trails for spring blossoming trees .
  • Drive to the historic Timberline Lodge and either take the chair lift to get to the summit or if you are up for an adventure there are tons of hiking trails behind the lodge. We did a section of the zigzag overlook trail which starts at the lodge parking area. Ask the lodge visitor center for more info on trails. Enjoy a nice early dinner or a cup of coffee with a view.
  • If you are not up for visiting the lodge then consider hiking the Mirror Lake loop trail that afternoon. We skipped the mirror lake loop.
  • Return to Government Camp for dinner unless you are staying back at Timberline Lodge.

A couple walking the trail to Mt. Hood mountain which is behind the Timberline lodge

ACCOMMODATION: Spend the night in Mt. Hood region. We stayed in a gorgeous farmhouse surrounded by apple & pear orchards booked through Airbnb . Your other best option is to stay at the historic  Timberline Lodge or hotels in Government Camp , a small town in Mt. Hood region.

how to travel to oregon

Day 5 – Explore Mt. Hood Region

Here’s what to do on your second day in Mt. Hood region –

  • Hit the Tamanawas Falls hiking trail in the morning (alternatively, you can do the Mirror Lake loop). Tamanawas trail is amazing, take our word for it.
  • Have your lunch at Tamanawas Falls. Pack your lunch with you so you can eat with the waterfall views at the end of the hike.
  • After lunch head to Trillium Lake in the afternoon. Walk along the lake trail or rent a kayak and enjoy the serene Mt Hood view from the water. TIP: Book your kayak rental in Govt Camp as there are no rental facilities at Trillium lake. The rental company will bring your kayak to the lake area. Don’t miss the sunset at Lake Trillium!  TIP: Bring mosquito spray, there are like a thousand of them here. You can also rent campgrounds at Trillium lake if you want to camp in this area.

ACCOMMODATION: We stayed back at the same farmhouse Airbnb with the perfect view of Mt. Hood. Your other best option is to stay at the historic  Timberline Lodge or hotels in Government Camp , a small town in Mt. Hood region.

A girl walking through wooden bridge over a river on a hike to tamanawas falls in Oregon

Day 6 – Smith Rock State Park, Painted Hills & 3 Sisters

As you drive south from Mt. Hood, take a day to explore the desert region of Oregon. You’d be surprised to know that a big part of Oregon is, in fact, desert land. What was really fascinating to us was that our families in India instantly knew about Oregon out of all the places. They were the ones to tell us about Rajneeshpuram.  FACT: Rajneeshpuram (from ‘Wild Wild Country’ series on Netflix) was not too far from this part of Oregon.

TIP: For a 7-day Oregon road trip, skip this section and head straight to Crater Lake from Mt. Hood.

  • Stop at Smith Rock State Park as you drive south from Mt. Hood region. and enjoy the gorgeous scenery.
  • Drive about 2 hours east to see the Painted Hills which are in the deep end of the Oregonian desert.
  • Reach Bend and head to Summit Park for a great view of the 3 Sisters volcano peaks .
  • If you want to get a better view of 3 sisters then drive 30 mins from Bend to Dutchman Flat Sno Park in Deschutes National Forest.

ACCOMMODATION: Spend the night in Bend, OR .

Where to Stay in Bend, Oregon

Element Bend

Campfire Hotel

Holiday Inn Express & Suites

colorful hills on the dessert side of eastern Oregon in USA

Day 7 – Crater Lake National Park

Crater Lake National Park is about 2 hours away from Bend or about 4 hours from Govt Camp. If you leave early in the morning, you can reach Crater Lake just in time to drive around the rim and see the following viewpoints & sneak in one easy hike.

Pick and choose your favorite spots to see in Crater Lake National Park , below are a few that we recommend –

  • Sinnott Memorial Outlook at Rim Visitor Center
  • Sun Notch (0.8 miles easy hike with views of Phantom Ship)
  • Phantom ship overlook
  • Discovery Point (2 miles)
  • Watchman Peak (1.6 miles moderate steep hike)
  • Pumice castle overlook,
  • Cloudcap overlook,
  • Vidae Falls
  • Pinnacles Overlook.

ACCOMMODATION: Spend the night in Crater Lake Lodge or campgrounds in the park . If you don’t get a reservation in either of these then consider staying in Fort Klamath or Chemult or Chiloquin which are small towns near Crater Lake. TIP: If you stay at Crater Lake Lodge, then don’t miss the splendid sunset from the lobby’s back patio.

View of crater lake blocked from the thick smoke cover of wildfires in the neighboring region of the National Park

PLEASE NOTE:   The Crater Lake itinerary was a part of our original plan until west coast wildfires & smoke completely ruined the experience. When we arrived at Crater Lake National Park, it became really difficult to breathe without inhaling the fumes. Not to mention, the visibility of the Lake was near zero. We had booked a campground for the night but for good reasons we decided to turn around. As a backup plan, we headed to spend more time on the Oregon coast. PRO   TIP: Watch out for wildfire and smoke reports in Oregon before you head here!

Day 8 – Umpqua National Forest & drive to Eugene

Next morning stop by the Crater Lake vista points that you might’ve missed on the previous day. On your way to the coast of Oregon, you must take a pitstop at Umpqua National Forest for a bonus waterfall & hidden hot springs.

  • Drive around Crater Lake in the morning to cover any missed vista points from the previous day.
  • Hike the  Toketee Waterfall trail in Umpqua National Forest as you exit Crater Lake. It’s an easy 0.8 miles round trip hike to the gorgeous waterfalls as you can see in our photos.
  • If you enjoy natural hot springs , then as you exit from Toketee waterfalls take a left and head to Umpqua Hot Springs . There is a $5/vehicle charge to park at the hot springs. Clothing is not enforced here so consider yourself forewarned. In full disclosure, we did not visit the hot springs due to a lack of time.
  • Drive to Eugene from Toketee Falls should take around 2.30 hrs.

ACCOMMODATION: Spend the night in Eugene, OR .

Where to Stay in Eugene, Oregon

Comfort Suites Eugene

Maverick Hotel

Graduate Eugene

toketee falls overlook in Oregon with lush green vegetation around it

Day 9:  Oregon Coast road trip

The next morning we headed to Florence from Eugene where we started our Oregon coast drive. The coastal drive takes you on Highway 101 which, in fact, is a continuation of California’s coast to Oregon’s.

Given that we just had one day set aside for this Oregon coast road trip, we only stopped at the vista points mentioned below in bold. We’ve listed some additional awesome pit stops along the way if you have more time.

  • Drive past Florence 
  • Heceta Head Lighthouse  Scenic Viewpoint (There is a B&B at this lighthouse now) or stop at Sea Lion vista point to see the lighthouse from a distance.
  • Cape Perpetua Overlook (Thor’s Well is another stop before turning right to Cape Perpetua overlook)
  • Yachats (stop by for a drink or early lunch)
  • Newport (If you skip Yachats then stop here for lunch)
  • Devil’s punchbowl and Otter Rock
  • Tillamook (stop by at the cheese factory or the Tillamook ice-creamery)
  • Cannon Beach, get here before sunset to watch the magic unfold

ACCOMMODATION: Spend the night in Cannon Beach, OR .

A girl standing at the vista point of Oregon Coastal view

Day 10: Lewis & Clark National Park OR Evergreen Aviation Museum

We took a red-eye back to the east coast since we wanted to squeeze every second of our last day. TIP: For a 7-day Oregon road trip, skip this part and fly out on your last day.

  • We visited the Evergreen Aviation & Space Museum in the morning but you can choose to visit the Lewis & Clark National Park near Cannon Beach to get an insight into expeditions that were an integral part of US history.
  • Head back to Portland to grab an early dinner before heading out to the airport for an evening flight.

Aircraft Museum in Oregon dispalying airplanes from US airforce and navy

Phew, another long guide, isn’t it? But there is so much to see & do here that you have to plan it right and we’ve to give all the right info to do so. And by the way, if Oregon wasn’t on your list, we sure hope it is now!

If you liked this extensive Oregon road trip planning guide then don’t forget to share it along with family & friends.

More on Travel in the United States:

  • America’s favorite road trip – the Blue Ridge Parkway
  • Bucket List Arizona Road Trip – The perfect long weekend 4-day itinerary
  • Best places to see fall colors in New Hampshire – A Roadtrip through New England
  • Ultimate SF to LA Road trip – Best stops along California’s Pacific Coast Highway

best Oregon road trip itinerary

Happy Traveling!

Related Posts

Portland Waterfalls & Wineries – Exploring Columbia River Gorge, Oregon

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23 comments on “ the perfect oregon road trip itinerary – 7 or 10 days ”.

Such a detailed guide. Thanks for sharing! Perhaps this fall my family and I will go to the Oregon. Awesome photos!

Thanks Michael. Hopefully the fires will be in control by then and the smoke out of OR skies. This year the wildfires have been terrible for Oregon.

Wow you really packed a lot in to tour trip. As someone who lives in Oregon, this is a great post. Come back soon!

We would love to!!! 😀

Wow! Mind blowing and eye catching photography. All places are just awesome. Hope to trip to those places in the near future. Stunning! You must (please) take me there when I visit. Thanks for sharing such a beautiful place.

You are most welcome and hope you visit Oregon someday 🙂

We did a Northern California road trip in June last year and did a tiny bit of Oregon so that we could try some of the wineries up there. I wish we’d done more of Oregon because it looks amazing and I’m filing your post for our next trip!

There’s always a next time 🙂

I’ve never visited the northwest USA but I really have to get there asap, this road trip looks amazing! 🙂

Yeah the Pacific Northwest is truly magical 🙂

Wow, great itinerary! I hope to come back to USA next year and was just looking into California and neighboring states for potential road trip ideas. Oregon looks an idea place to visit! Love the nature and national parks

Oh yes definitely visit OR if you are coming to CA, you will love it! 🙂

Oregon is such a beautiful state, I can’t wait to spend more time there. This looks like a really good way to see a lot of the state in one well, a great itinerary. I live in Vancouver Canada so this is such a doable trip for me

Oh yeah, definitely easily doable from Vancouver. I believe there is an easy train ride from Seattle to Portland, wonder if there is a train from Vancouver to Portland as well?!

I love a good road trip! Thanks for sharing these great places in Oregon 🙂

Most welcome! There’s nothing like sharing cool places to do a great road trip. 😀

We did a similar trip a few years ago, but looks like we missed the Umpqua National Forest. Oh well! Looks like we just need to head back.☺️ Thanks for the post!

You’ve got to leave something out to return back to such amazing places right?! 😉

I had no idea Oregon was this beautiful! I love the suggestion of seeing the state through a road trip, definitely saving for later 🙂

Yeah, this is one of the perfect States to visit in one road trip 🙂

There is obviously plenty to do in Oregon. My personal goals for almost any trip is to do lots of hiking and visit lots of breweries and wineries. I didn’t know that you could have your gas filled by station attendants there. I think I might plan a trip there for that alone. It would be so cool!

It’s great to learn that you should stay downtown when going on a trip to Portland. My wife and I are looking to travel to Oregon soon and we were wondering where we should stay at in the state. I’ll be sure to let my wife know that we can stay in downtown Portland.

Oh yes, Portland is so close to a lot of nature in Oregon. However, if you want to do a road trip around the entire State then as mentioned above you might have to pick other cities for overnight stay esp when going down south or east.

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Hello from Gaurav & Richa! An adventurous couple who did NOT quit their corporate jobs to travel the world. On the contrary, we're all about balancing that work-travel life. Our goal is to explore as much as we can in our short vacations and yes, we do go to great lengths to find unique experiences and great food to share with you all. Learn more About Us .

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Oregon is for Adventure

Your Ultimate Oregon Road Trip—1 Week to 1 Month Oregon Itinerary

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We can’t lie, writing up this ultimate itinerary for an Oregon road trip was HARD.

We couldn’t stop, we kept writing and writing, and next thing you know, we came out with this monster Oregon itinerary that could last you around a MONTH. Yes, an entire month around Oregon.

As epic as that would be, we know that not everyone has 30 days to traverse our massive, stunning, and truly adventurous state .

With that said, we weren’t going to deprive you of choices! So, welcome, this just may one of the longest and craziest posts on road-tripping Oregon out there.

Don’t get intimidated; we laid everything out very easily for you to pick and choose and personally curate your own legendary Oregon road trip.

Fill up your gas, grab your supplies, and head on out!

Table of Contents

Your Ultimate Oregon Road Trip Itinerary

Ecola state park – 1 day, arch cape – 1 day, cape meares – 1 day, sand lake recreational area – 1 day, lincoln city –  1 day, depoe bay – 1 day, yaquina head – 1 day, cape perpetua – 1 day, sea lion caves – 1 day, shore acres state park – 1 day, samuel h. boardman state scenic corridor – 1 day, where to stay on the oregon coast, mount hood – 2 days, silver falls state park – 1 day, columbia river gorge – 1 day, where to stay near portland, deschutes river – 1 day, umpqua national forest – 1 day, smith rock state park – 1 day, cascade lakes scenic byway – 1 day, three sisters wilderness – 1-2 days, newberry crater national volcanic monument – 1 day, crater lake – 1 day, where to stay in central oregon, wallowa mountains – 2 days, sumpter – 1 day, mitchell – 1-2 days, strawberry mountains – 1 day, umatilla national forest – 1 day, owyhee canyonlands – 1-2 days, steens mountain – 1-2 days, hart mountain – 1 day, summer lake – 1 day, where to stay in eastern oregon, an oregon road trip itinerary, tips for your oregon road trip, a legendary oregon coast road trip—35 stops & 3 itineraries, 29 awesome things to do on an eastern oregon road trip, 19+ adventurous things to do on a washington road trip, 21+ adventurous things to do on a northern california road trip, 25 day trips from portland, oregon + road trip ideas.

For the sake of ease, we’ve sliced up Oregon into four sections. The Coast , Central , Near Portland , and then East Oregon .

We know this split isn’t an accurate representation of how Oregon is divided, but we think a good chunk of people reading this may not be from Oregon and, therefore, can digest the vastness of the state a bit easier this way.

Of course, as per usual, we also offer you a handy little map because visuals are ALWAYS better when planning out a road trip, always.

how to travel to oregon

Below you’re going to read about some of our favorite highlights from each section of Oregon, and each section will need at least a week to ride through and experience. You may not be able to hit up every highlight we have here, but we had to give you some choices.

We’ve also included the number of days next to each spot. Do note, this is the absolutely MINIMUM amount of time you’d need. Most will state one or two days, and we mean an entire day or two.

This will just give you a taste of the area, or if it’s small enough, a single day may really be all you need.

Also note this is not included driving. Again, it’s a full day of exploring, hiking, rock climbing, out on the lake with your sport of choice, etc… Please add in driving days as needed.

As we like to mention here often, particularly from visitors to the USA, our country is freakin huge, dudes! Like, mega massive. So please plan accordingly.

Driving around the USA, and yes, that means Oregon too, requires more time than you think. Always add on an hour or so to the estimation Google Maps gives you to be safe.

We’ve also added in tons of additional links through this post which give you a deeper dive into a lot of the places and areas mentioned here so click those for more info.

Anyway, get your travel pants on, snacks stocked, and let’s get this Oregon road trip rolling! Right?

✋ HOLD UP! Don’t Forget…

You need some wheels! It’s nearly impossible to get around the USA and check out the best adventures without a car! Here are our top recommendations…

🚗 Rent a car

If you don’t have your own, renting a car is your best bet!

👉 Find Deals on Cars and SUVs

🚐 Rent a home on wheels

For the more adventurous, rent a van or RV and ditch the hotel.

👉 Find The Best Van For Your Trip

Don’t Forget This!

A lot of the best adventures around Oregon will require a Northwest Pass. You can easily get one delivered straight to your door. Grab it now before you leave !

how to travel to oregon

Oregon Coast Road Trip Itinerary

The rugged Oregon coastline is one of those places that feels like you’re living in a dream. Stretching for over 360-miles against the wild Pacific Ocean, the Oregon Coast is loaded with awe-inspiring natural scenery and vibrant communities.

Places on the best Oregon Coast road trip

From its serene beaches to towering sea stacks, each section of the coast will keep you on the edge of your seat during your Oregon road trip.

Sandy beaches, craggy cliffs, scenic viewpoints, lush forests, alluring tide pools, shipwrecks, rolling sand dunes, and monstrous waves are all accessible just off the highway. What more could you want for a life-changing Oregon itinerary?

Have your camera ready and explore the picturesque coastline that has captured the hearts of Oregon lovers everywhere!

  • Explore the never-ending hiking trails through its tranquil forests like the Clatsop Loop and Crescent trails.
  • Capture a breathtaking panorama at one of Oregon’s most famous viewpoints. From atop the cliffside, you have the perfect angle of towering rock formations rising out of the ocean.
  • Head to Indian Beach to spot tide pools and have a relaxing picnic while you listen to the waves crash against the shore.

READ MORE: Your Guide to Ecola State Park on the Oregon Coast

Don't forget to stop at Ecola State Park on your Oregon road trip.

  • Experience blissful solitude while feeling the sand between your toes on this pristine shoreline.
  • Explore the enchanting caves, gorgeous waterfall and shallow tide pools of Hug Point State Park .
  • Get a brilliant bird’s eye view of the Pacific Ocean, long stretches of the coastline and the coastal town of Manzanita at the Neahkahnie Viewpoint.

Add Arch Cape Beach to your Oregon itinerary.

  • Add a detour along the Three Capes Scenic Route to your Oregon itinerary for a sensational drive down the Tillamook coastline. The journey takes you to Cape Lookout and Cape Kiwanda for miraculous views of verdant forests and sand dunes.
  • Go bird watching to see colonies of nesting murres and other beautiful avian species.
  • Wander inside the Cape Meares Lighthouse for a thrilling view on the cliffside roughly 200-feet above the ocean.

RELATED: Three Capes Scenic Route on the Oregon Coast

  • Go off-roading through sand dunes in between the crashing waves of the Pacific and a coniferous forest.
  • Spend the night camping at this enormous lake of sand and witness a dreamy sunrise against the ocean.
  • Spend the night at one of the most scenic Oregon coast towns by camping at Devil’s Lake near downtown Lincoln City . The lake offers a wide range of outdoor activities such as fishing, kayaking, and hiking.
  • Enjoy a day on the water at Siletz Bay by kayaking, boating or fishing on its tranquil shores.
  • Hike the God’s Thumb via the Knoll, one of the most breathtaking Oregon Coast hikes . The end of the trail features a peculiar basalt formation shaped like a thumb offering sensational views of the coastline.
  • Check out the interesting statue of Abraham Lincoln and waltz through the town’s Historical Museum.

READ MORE: Your Guide to the God’s Thumb Hike Near Lincoln City

  • Stop by the Whale Watching Capital of the Oregon Coast during this Oregon road trip to search for majestic gray whales.
  • Just south of the whale hotspot, you’ll find the roaring power of the Devil’s Punchbowl. This enormous bowl was created by collapsed sea caves and gives you a glimpse of the ocean’s power with its ferocious waves.

Depoe Bay on the Oregon coast road trip

  • Tour the Yaquina Head Lighthouse, the tallest and most historic lighthouse in Oregon. Tickets to the lighthouse are on a limited basis but the panoramic views of the structure perched along the scenic bluffs are some of the best on the entire Oregon coast.
  • Hike the rocky shoreline beneath the lighthouse to spot whales, seals, eagles and beguiling tide pools.
  • Drive to the highest Oregon coast viewpoint accessible by car and stand in awe of the hair-raising vista overlooking the horizon. You’ll be standing 800-feet above the crashing waves of the Pacific Ocean and this stop on your Oregon itinerary will make your heart skip a beat.
  • Marvel at the geologic formations of Thor’s Well and Devil’s Churn. Thor’s Well is a seemingly bottomless pit sucking waves into its grasp and Devil’s Churn will overwhelm you with the force of tenacious waves pounding a rocky inlet.

Hillside of the Cape Perpetua on an Oregon road trip.

RELATED: 9 Things to Do in Cape Perpetua, Oregon

  • Ride the elevator to the depths of the largest sea caves in the United States. Keep in mind that this includes a fee of $14.
  • Spot adorable sea lions lounging inside the massive cave system. If your Oregon road trip is during the winter, then there is a great chance you’ll see hundreds of these amazing creatures.
  • Head to the nearby Heceta Head Lighthouse for a remarkable view standing atop a rocky cliff.
  • Stand at the park’s scenic viewpoint and witness thunderous waves pounding the jagged rock formations on the coastline.
  • Wander the grounds of a former mansion to smell the radiant flora of rose gardens and a Japanese-style garden.
  • Walk along the shores of Simpson Beach and relax at its isolated cove.

Foam at cliffs of Shore Acres State Park for your Oregon itinerary.

  • Explore the miles of beautiful coastal trails the Samuel H. Boardman State Scenic Corridor has to offer. The Lone Ranch South Trail is an easy trek offering breathtaking seaside vistas and the Whales Head Beach Trail meanders to one of the most peaceful beaches in the corridor.
  • Hike to the Natural Bridges for spectacular views of geologic structures and spruce-tree forests.
  • Enjoy the serenity of Secret Beach and gaze at the towering rock formations nestled along the shore.
  • Before continuing your Oregon road trip, peek through the forest and watch a gorgeous sunset at Arch Rock.

Samuel H. Boardman ― A great stop on your Oregon road trip.

Southern Oregon Coast: 13 Epic Stops—Bandon to Brookings!

17 Breathtaking Oregon Coast Hikes

11 Most Scenic Oregon Coast Towns (And What to Do There!)

17 Cool Oregon Coast Camping Spots To Stay At

→ If you don’t have a lot of time, do this Oregon Coast day trip from Portland to see the best of the coast with a local.

Recommended Places:

  • Adorable Seaside Cottage
  • Happy Camp Beachfront Cabin
  • Captain’s Quarters

Campgrounds: Wright’s for Camping | Devil’s Lake State Recreation Area | Harris Beach State Recreation Area Campground

Near Portland, Oregon Road Trip Itinerary

We love Portland , naturally. But we love the places on the outside of Portland way more.

Cascading waterfalls galore, a cornucopia of excellent hikes, and the majestic Mount Hood just on the outskirts of the city make Portland a playground for Oregon adventurers.

After you’re done stuffing your face with Voodoo donuts and taking the iconic “Portland is weird” sign selfie, then get out and do something in nature!

Dry Creek Falls in it's entire splendor

The furthest you’ll drive from Portland to anything in this section is only about two hours one way. You’ll be gobsmacked by the things to do just outside the concrete jungle of Portland.

  • Enjoy spectacular views of Oregon’s tallest mountain from all angles by embarking on many awesome Mount Hood hikes . Some of the best hikes include the Tom Dick and Harry Trail and Mirror Lake Loop , Lost Lake, Tamanawas Falls , and the Trillium Lake Loop and they all give you glorious vistas of Oregon’s most famous peak.
  • Summit the craggy pinnacle and have the exhilarating feeling of standing on the roof of Oregon.
  • If you have a snow-filled Oregon itinerary, experience Mount Hood in winter by skiing or snowboarding down its slopes. Just be aware of possible road closures in the area around the mountain during winter.

Hiker looking up at Tamanawas Falls in Oregon

→ If you don’t have a lot of time, do this Mount Hood Day Trip from Portland to see the best of the area.
  • Hike the Trail of Ten Falls to experience one of the most beautiful hikes near Portland. The 7.6-mile loop passes ten alluring waterfalls and is considered one of Oregon’s natural wonders.
  • Hit the park’s backcountry trails for mountain biking and horseback riding adventures.
  • Spend the night at the campground and listen to the soothing sounds of the waterfalls before continuing your Oregon road trip.
  • Capture the perfect snapshot of Oregon’s most famous waterfall in all her glory—Multnomah Falls
  • Discover more cascading waterfalls in the Columbia River Gorge by hiking the Wahkeena-Multnomah Loop. This invigorating trek takes you through lush vegetation, volcanic cliffs and far away from the crowds.

A stop at the Vista House on your Oregon road trip is a must.

17 of the Best Places for Camping Near Portland

19+ Awesome Hikes Near Portland to Escape the Bustle

What to Do At Mount Hood in Winter

A Guide to The Columbia River Gorge

→ If you don’t have a lot of time, do this highly rated half-day tour from Portland to see the best waterfalls in the Columbia River Gorge.
  • Tiny House With Lofted Views of the Forest
  • Peaceful Garden Cottage
  • Tiny Forest Cabin

Campgrounds: Beaver Campground | The Vintages Trailer Resort | Oxbow Regional Park 

Central Oregon Road Trip Itinerary

When it comes to jaw-dropping natural scenery, it’s impossible to replicate the magic that central Oregon presents. There’s a reason why many of the state’s most iconic sights are in this dynamic region.

From the majestic Cascade peaks to the tumbling waterfalls of the Columbia River Gorge , Central Oregon has it all.

South Sister is an epic hike in Oregon

This portion of your Oregon road trip transports you to several of the state’s tallest mountains, evergreen forests, crystalline lakes, and mysterious craters. The biggest challenge will be narrowing down your Oregon itinerary to fit your schedule.

Central Oregon’s diversity is simply unmatched and traveling down its scenic byways will show off its splendor at every turn.

If you’re looking to experience Oregon at its absolute finest, central Oregon has got you covered!

  • Climb into a raft and float down the Deschutes River for an afternoon of total relaxation.
  • Enjoy more exciting activities by the river like kayaking, fishing or even take a crack at surfing .
  • Hike the Deschutes River South Canyon Trail or the Deschutes River Trail Loop for a delightful stroll by the river.

If you're looking for adventurous things to do in Sunriver, be sure to check out the Deschutes River trail.

  • Camp in the tranquil forest and hike through pine trees, wildflowers and dense vegetation to reach many mesmerizing waterfalls. The Toketee Falls Trail, Watson Falls Trail and Lemolo Falls Trail are among the scenic paths in Umpqua National Forest .
  • Venture down the Twin Lakes Trail for sensational views of dazzling lakes and find the perfect spot for a picnic.
  • Soak in the terraced pools of the Umpqua Hot Springs and watch the peaceful flow of the Umpqua River.
  • Kayak on the shimmering waters of Diamond Lake as the ‘lightning rod’ Mount Thielsen towers above you. For an action-packed expedition to include on your Oregon road trip, get your adrenaline pumping on the Mount Thielsen hike to reach the summit of the jagged peak.

Add Umpqua National Forest to your Oregon itinerary.

  • Hike along the Crooked River and gaze at the craggy pinnacles rising high into the sky.
  • Test your endurance by climbing Misery Ridge and watch rock climbers test their wits at the oddly shaped Monkey Face.
  • Learn how to rock climb yourself since this stop on your Oregon itinerary is the premier location in the state for the sport.
  • Marvel at golden eagles, rattlesnakes, otters and other beautiful wildlife that call these sharp canyons home.

Don't miss Monkey Face during your Oregon road trip.

  • Visit the sparkling lakes decorating this famous driving route such as Todd Lake, Sparks Lake and Elk Lake . This 66-mile highway takes you from the vibrant city of Bend to some of the most popular getaways in central Oregon.
  • Stand in awe of the snow-capped Cascade peaks overlooking the alpine lakes lining the byway. Mount Bachelor , Broken Top Mountain and South Sister are a few of the iconic mountaintops in perfect sight.
  • Enjoy an abundance of outdoor activities by the lakes such as fishing, hiking, mountain biking and paddling.
  • You have countless camping options to include in your Oregon road trip for an extended stay near the byway.

Don't forget to add Sparks Lake to your Oregon itinerary.

  • Gear up for one of the ultimate challenges on this Oregon road trip by tackling the South Sister Trail . This 12.2-mile trek takes you to the peak of Oregon’s third-highest mountain and rewards you with jaw-dropping vistas of the nearby peaks.
  • Take on another daring expedition by trekking the Broken Top Trail to No Name Lake and Bend Glacier. This thrilling hike will take you through subalpine forest and provide a close encounter with Broken Top’s serrated pinnacles.
  • If you have time, hike part of the Three Sisters Loop to marvel at the area’s volcanic landscapes.

RELATED: Your Guide to Hiking South Sister in Bend, Oregon

  • Admire the otherworldly geologic landscapes and the remnants of powerful volcanic blasts from thousands of years ago at Newberry National Volcanic Monument .
  • Hop on your mountain bike and ride around the Newberry caldera using the rim trail.
  • Hike the Paulina Peak Trail to experience one of the best Oregon hikes and possibly the most awe-inspiring vista in central Oregon. The views here give you 360-degree views of Paulina Lake, the Big Obsidian Flow and other peaks of the Oregon Cascades.

Paulina Peak is a cool place to stop on your Oregon road trip.

READ MORE: Your Guide to Newberry National Volcanic Monument

  • Include the Rim Drive on your Oregon road trip to conquer the 33-mile loop that circles the caldera rim.
  • Hike the Garfield Peak Trail for incredible scenery overlooking the deep-blue hues of the lake and the surrounding Cascade peaks. You’ll have a spectacular view of Phantom Ship, Wizard Island, and other beautiful landmarks.
  • Head to Cleetwood Cove for an interesting vantage of the lake from inside the caldera.

Crater Lake is another beautiful place to stop on your Oregon road trip.

A Guide to Smith Rock State Park’s Hikes, Misery Ridge Trail & More

  • An Adventurer’s Guide to Things to Do in Bend, Oregon

The Tamolitch Blue Pool Hike + Sahalie and Koosah Falls

  • Cozy Sunriver Cabin
  • Hummingbird Cottage
  • Tall Pines A-Frame

Campgrounds: Elk Lake Campground | Jasper Point Campground | Redmond/Central Oregon KOA

Eastern Oregon Road Trip Itinerary

Very few people are in the loop of the majestic scenery decorating the eastern half of Oregon. And it’s a shame that this section of the state doesn’t receive the same hype as its coast and Cascade brethren.

Sparkling lakes, snow-capped mountaintops, mesmerizing deserts, craggy gorges, verdant forests, striking canyons, rejuvenating hot springs and some of the best stargazing on the planet.

how to travel to oregon

With this much jaw-dropping natural beauty, it’s hard to fathom that this is the least discovered region of Oregon. Maybe it’s best to keep it that way to preserve this wild canvas of untouched terrain.

It may sound cliché to wander off the beaten path, but that is exactly the type of adventure eastern Oregon provides on your Oregon road trip.

  • Explore the rugged terrain of the Wallowa Lake State Park by trekking the Hurricane Creek Trail or para-glide above the park for a once-in-a-lifetime experience.
  • Swim in the pristine waters of Wallowa Lake surrounded by dense forests and rugged peaks. Its crystalline waters are a beautiful spot for snorkeling, or you can sunbathe on the sandy shores for a tan.
  • Ride the Wallowa Lake Tramway for unbelievable mountain vistas.
  • Trek the Mirror Lake to Eagle Cap Trail to reach the summit of Eagle Cap. Enjoy the sensational views of alpine lakes, beautiful forests and glaciated valleys.
  • Grab your paddle and steer around jagged boulders in the exhilarating class III and IV rapids of Eagle Creek.

Hurricane Creek Trail at Wallowa Lake State Park should be added to your Oregon itinerary.

  • Dress up like Wild West characters at the charming Sumpter Stockade Motel.
  • Learn about Oregon’s rich gold mining history with a visit to the Sumpter Valley Dredge .
  • Spend an exhilarating day riding around on an ATV before hopping back on the highway.

View of Sumpter Train Station on your Oregon road trip.

→ While in Sumpter, head to nearby Baker City to do some stargazing and wine tasting on this fantastic tour .
  • Hike through the Ochoco National Forest for remarkable images of lush forests, bewildering geologic formations and vibrant wildlife. Its tranquil waterways are the perfect outlet for a fishing or boating excursion.
  • Discover the otherworldly beauty of the Painted Hills , one of Oregon’s greatest natural treasures. The layered bands of yellow, red, orange and gold make the perfect stop on your Oregon itinerary to marvel at the state’s alien-like landscapes.
  • Explore the hiking trails less-visited around the John Day Fossil Beds area to study Oregon’s ancient history. Sheep Rock and the Clarno Unit are both a must for geology lovers.

Don't forget to make a stop at the Painted Hills on your Oregon road trip.

  • Unleash your adventurous spirit by hiking through the less-traveled Strawberry Mountain Wilderness. This nature lover’s playground is teeming with alpine lakes, sharp peaks, blooming wildflowers and an abundance of wildlife.
  • Reach the peak of Strawberry Mountain for one of the most liberating summits on your Oregon road trip. The heart-racing vistas hear make you feel like you’re on top of the world.
  • Unwind in the great outdoors at the crystal clear waters of Strawberry Lake. This is an ideal camping spot for your Oregon itinerary with its lush forests, rugged mountains and quality fishing.

Strawberry Mountains are a great place to add to your Oregon itinerary.

  • Spend the night at Jubilee Lake Campground for another beautiful night underneath the stars during your Oregon road trip. Jubilee Lake is a peaceful hideout deep in the forest and a wonderful spot to escape the scorching temperatures of summer.
  • Enjoy a tranquil ride down the class II rapids of the Grande Ronde River and gaze at the steep canyons rising above you.
  • Watch for deer, bighorn sheep, eagles and other wildlife (including rattlers) on the roughly 30-mile Wenaha River Trail. The meandering river, towering cliffs and tranquil forests make this a fantastic backcountry adventure to add to your Oregon itinerary.
  • Experience one of Oregon’s most exciting whitewater rafting excursions on the Owyhee River. The class III and IV rapids snake between basalt columns and red-rock cliffs creating an unbelievable ride.
  • Explore some of Oregon’s most isolated hiking trails through the Owyhee Canyons and marvel at the sheer-canyon walls soaring above you.
  • Make the Owyhee Canyonlands another one of your camping sites on your Oregon itinerary for a stellar night of stargazing.

The Pillars of Rome for your Oregon road trip.

  • Push your adrenaline to the max by driving the 60-mile Steens Mountain Loop, one of the most thrilling routes to add on your Oregon road trip. This scenic route will leave you speechless with its contrasting landscapes of glacial gorges and barren deserts while taking you to elevations of nearly 10,000-feet.
  • Capture a breathtaking panorama on the Wildhorse Lake Trail. The views of the glaciated valley and steep canyons offer one of the top vistas you’ll see on this Oregon road trip.
  • Camp in the Alvord Desert to experience complete solitude in the Oregon wilderness. Make sure to visit Alvord Hot Springs to soak any aching muscles before hitting the road again.

Camping in Alvord Desert is a fun thing to do on your Oregon road trip.

  • Wash off the dust from Oregon’s extensive desert by soaking in the relaxing Hart Mountain Hot Springs . Camping is free at the hot springs so make sure to arrive early if this is an overnight stay on your Oregon itinerary.
  • Wander the hiking trails of the National Antelope Refuge and spot a plethora of wildlife in their natural habitat.
  • Jump on your dirt bike or motorcycle to ride the desolate dirt trails cutting through the landscape.

The road to Hart Mountain is another great spot to add to your Oregon itinerary.

  • Go bird watching in the wetlands of the lake and marvel at the area’s geothermal wonders.
  • Gaze at the sensational mountain scenery while you soak in the soothing pools at the Summer Lake Hot Springs.
  • Drive the car out to Fort Rock for an enchanting sunset at this puzzling volcanic landmark.

Relax at the Summer Lake Hot Springs after a long day on your Oregon road trip.


Exploring the Owyhee Canyonlands: Hiking, Rafting, & Camping

A Guide to Hart Mountain Hot Springs & What to Do in the Area

A Comprehensive Guide to Visiting Wallowa Lake State Park—Adventures and Camping

7 Awesome Things To Do in Sumpter, Oregon

  • Rich’s Camp Cabin
  • Eagle Cap Chalets
  • Dreamers Lodge

Campgrounds: Wallowa Lake State Park | Strawberry Campground | Jubilee Lake Campground

how to travel to oregon


Tried and tested gear that we use around Oregon and the PNW!

Hiking and Camping

  • Water Bottle Filter  
  • Camping Stove
  • Camping Cook Set
  • Light 2-Person Tent
  • Car Trash Bin
  • Car Power Inverter
  • Road Trip Duffel Bag
  • Northwest Pass

Clothing Gear

  • Hiking Socks – Men’s / Women’s
  • Rain Jacket – Men’s / Women’s
  • Hiking Backpack – Men’s / Women’s

Car Rental:

  • Car Rental – Check here for deals
  • Outdoorsy – For Vans, RV, etc

It’s safe to say all the above is just scratching the surface of what you can see on an Oregon road trip! With that said, everything mentioned above would take about a month to actually experience. Yep, a whole goddamn month!

Catch these gorgeous views on your Oregon road trip.

Oregon is not a small state and it takes a long time to traverse.

I’d encourage you to check out our more specific Oregon road trips depending on the region you’re most interested in.

  • 37 of the Best Oregon Hikes You’ve Got to Check Out

Each area mentioned above deserves at least a week of exploring. And when we say a week, we mean a week of actual exploring!

The driving can take up a really large chunk of the day so we’d advise you to tack on an extra few days on top of the week to account for driving or rest days.

Extending your road trip to our neighbors? Check these posts out!

  • 19 Adventurous Things to Do on a Washington Road Trip
  • 21 Adventurous Things to Do on a Northern California Road Trip
  • If you’re looking to save a buck, download Gas Buddy App. As a rule of thumb, always fill up at the bigger towns when you can. The smaller towns often cost more, and if you pay by card, you may have a transaction fee on top of it.
  • I’ll say it once more just in case, Oregon is not small! It will take you longer than you think to get places. I know my fellow Americans will get it but if you’re a visitor, our country and our states are insanely big. I can’t stress it enough, it will take you longer than you think.
  • If you plan on visiting many of the places on this list, just get a parks pass instead of paying $5 randomly here and there for parking. The pass is $30 and you can display it and forget it.
  • Bring food! Having to find food, particularly for breakfast and lunch, will eat up a considerable chunk of your day. Don’t waste hours on eating. Have snacks, sandwiches, and other quick things to munch on throughout the day and then save eating out for dinner.
  • As far as budgeting goes, you can do this Oregon road trip on a modest budget. Many state parks have campgrounds that range from $15 to $25 per night. Check out these Oregon campgrounds .
  • If you’re here in the peak season (summer months) campsites and hotels get booked out so make sure to book sooner rather than later.
  • Be careful driving at night, particularly on the lonely roads. Animals like to come out and play. It’s best to keep your driving during daylight hours.
  • If you’re coming to Oregon in winter , or even just before/after, be aware of road closures .
  • For car rentals, we always check here .

More Road Trips

how to travel to oregon

We hope this helped you plan some fun road trips in Oregon! Be sure to check out our other posts on road trips .

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I've been perpetually traveling and living around the world for years but it's hard to beat Oregon and the PNW. After years of road-tripping the area, I guess you can say I know it pretty well! When I'm not writing guides for you, you can catch me somewhere petting a dog, attempting to surf, hiking a volcano, or stuffing my face with bread and cheese.

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how to travel to oregon


The State of Oregon is home to some of the most diverse landscape and scenic views in the entire United States. A beautiful coastline, over 360 State Parks, and home to some of the top rated breweries and restaurants in the nation, you will never run out of things to do while you’re here. Here at Visit Oregon, we’re passionate about those we get to share our great state with. We are your one stop shop for what to do, what to see, and where to stay. We may be biased, but we’d like to think Oregon has it all – come visit us and make memories to last a lifetime.

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The Ultimate Oregon Road Trip: Itinerary Inspiration and Must-See Stops

last Updated: May 17, 2021 bend cannon beach crater lake mt hood oregon portland road trip

FYI: Affiliate links may be sprinkled throughout the awesome, free content you see below. I’ll receive a small commission when you purchase from my links (at no extra cost to you), which I’ll totally blow on adult things like boba tea and avocado toast. As always, thanks for the support.

Are you ready to be blown away by shimmering lakes, snowy mountain tops, and enough craft beer to last a lifetime? Get ready for an Oregon road trip, my Pacific-Northwest-craving friends. Sharing tons of details below to get you started planning your trip to the Oregon coast and beyond!

Just last year I had never visited Oregon before. Yeah, yeah, shame on me (I kiiinda recently moved to the west coast so you’ll cut me some slack, yea?) ;p I visited for the first time last year, and let’s just say I’m a tad obsessed. I had heard Portland was kinda cool, and after one look at Crater Lake I knew I had to make it there sooner than later. Alas, my first few trips to Oregon were planned, and I’ve now found myself in the state 3 times within a ~6 month period (something that just NEVER happens).

Heading to Oregon and wondering what all the things to do in Crater Lake are?! Click through for the best hikes, best viewpoints, where to stay, and what to eat - exactly what you need to plan your own visit to Crater Lake!

So without further ado, I’m sharing my ideal Oregon road trip, from the quirkiness that is Portland south to the dazzling still water of Crater Lake and west to the allure that is the stunning Oregon coast.

Oregon Road Trip Itinerary Overview

  • Stop 1: Portland (2-3 days)
  • Stop 2: Columbia River Gorge/Multnomah Falls (1 day)
  • Stop 3: Mt. Hood (1 day)
  • Stop 4:  Silver Falls State Park (1 day)
  • Stop 5: Smith Rock State Park (½-1 day) 
  • Stop 6:  Painted Hills (½ day)
  • Stop 7: Bend (1-2 days)
  • Stop 8: Crater Lake (1-2 days)
  • Stop 9: Ashland (1 day)
  • Stop 10: Coos Bay / Southern Oregon Coast (1 day)
  • Stop 11: Newport, Tillamook, and Cannon Beach (1-2 days)
  • END: Portland

Over the course of the road trip, expect to drive approximately 24 hours (round trip) and around 1000 miles. You’ll notice on the map below that I haven’t included the drive from Portland to Silver Falls State Park (that’ll add another 2 hours or so to the time listed on the map), as well as the 1.5 hour drive back to Portland from Cannon Beach (limits of technology). In order to complete this Oregon road trip in a timely manner (a week to 10 days or so), you’ll be driving almost every day, with some being longer driving days than others. Plan accordingly and bring snacks! The time in the car doesn’t have to be absolutely horrible. :p

→ Read next: Top Tips for Long Car Trips // Long Road Trip Essentials

Planning an Oregon road trip? This post has everything you need, from where to stop, where to sleep, and top things to do in each place!

When to Visit Oregon

Like the rest of the Pacific Northwest, Oregon experiences four seasons. To be completely transparent (and as noted above), I visited these different spots in the state on a few different occasions. I visited Portland in early June, Crater Lake in early September, and Bend in the snowy winter months. Oregon is spectacular year round, but if you’re on the hunt for some sunshine and minimal precipitation, I’d recommend planning your Oregon road trip between the months of April and September.

The best month for visiting the Oregon Coast is typically September, as the summer months are usually pretty foggy. It’ll be the wettest throughout the state between November and March, and the warmest between June and September. The roads around Crater Lake typically don’t fully open to cars until July, so keep this in mind if you’re visiting prior!

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

If you have the luxury of picking exactly when to take your Oregon road trip, choose September! The weather is glorious – little to no rain, clear coastlines, and warm weather. Just like my home state of California, Oregon typically experiences an Indian Summer, which lasts until early-mid October.

Getting to Oregon (and Portland in particular)

First things first, if you’re not a resident of Oregon, you’ll of course need to get yourself there! Since PDX is a major international airport, it’s wise to start your Oregon road trip in Portland, as you’ll be able to find decently priced tickets from throughout the US, highly dependent on the airport you’re departing from. For reference, from SFO (San Francisco), I commonly see round trip tickets to PDX (Portland) for under $200, and many times under $150.

New Yorkers can fly to Portland for roughly $300 if bought far enough in advance. I swear by Skyscanner and Google Flights whenever searching for tickets, and more often times than not, find the cheapest prices on one of them. The ability to track prices (and get email notifications when the price drops) is top notch and one of my favorite features. Take advantage of Skyscanner , you guys, they’re seriously the best.

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

quirky coffee shops everywhere you go in Portland – this one’s in a converted school bus!

If you’ll be following this complete Oregon road trip itinerary you’ll be doing a full loop from Portland, hence the need for round trip tickets from PDX. If you’re coming from Northern California and don’t mind doing a bit of extra driving, you can start this road trip from wherever you see fit (Crater Lake is roughly 7-8 hours from San Francisco, and the southern Oregon Coast – Coos Bay – is about 9 hours). Just remember that you’ll need to head back to your original destination. 🙂

Since this is in fact a road trip , you’ll need a vehicle to get you from place to place! Worth mentioning so you don’t forget to account for the cost of a rental car when following this Oregon road trip! And since you’ll be returning the car in the same place you picked it up, no need for pesky extra drop-off fees. I commonly use this booking site when searching for low-cost car rental options, and like Skyscanner , frequently find great deals on there!

I like to search  via this site in order to compare rental companies to see who has the best price.

How Long Should This Oregon Road Trip Take?

In all honesty, that’s a kinda hard question to answer, as the duration of the trip highly depends on your interests and how long you wanna stay in each place. I’d say a week if you’re picking and choosing a few stops to 2 and a half weeks if you wanna see and do mostly everything on this Oregon itinerary at a leisurely pace.

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

Now let’s get this Oregon road trip under way!

The Complete Oregon Road Trip Itinerary

Stop #1: start in portland (2-3 days).

Portland, Oregon is best known for its delectable donuts, snobby coffee culture, orgasmic food, and, of course, for being weird. It is in their slogan after all! Two to three days in the city will give you enough time to see all the highlights, as well as eat to your heart’s content. It’s the best place to start your Oregon road trip since renting a car will be easy peasy if you’re flying into PDX.

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

With two days in Portland, you can easily fit in these activities:

  • Pittock Mansion: Looking for spectacular views of the entire city? You’ll find those here at Pittock Mansion. Note that while the view is free to admire, a ticket is required to tour the mansion grounds.

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

  • International Rose Test Garden (located within Washington Park): What’s better than rows and rows of sweet-smelling roses? Hint: not much. The garden boasts over 10,000 of the pretty things, in every color combination imaginable (over 650 varieties)! Wander around for a half hour or so, and be sure to actually stop and smell the roses (yes, pun intended). Make sure you visit when the roses are in bloom (April through October, although June is the peak season). FYI – Entrance to the garden is free, but you’ll need to pay a few bucks for parking.

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

  • Powell’s City of Books: Book lovers, rejoice! You can easily spend hours (and hours) exploring Powell’s flagship store – you’ll even need a map (which they happily supply). Be warned: this place is HUGE huge (like, multiple floors with rooms opening into rooms opening into rooms, etc etc). It actually takes up an entire city block and then some. If you can’t find what you’re looking for, you’re just not looking hard enough – they have EVERYTHING imaginable and then some (new, used, rare, and even out-of-print books). I was like a kid in a candy store…

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

  • Keep Portland Weird Sign: Right across from Voodoo Donuts you’ll find this quick photo spot → don’t miss this iconic mural! The sign itself is just a wall in a parking lot, but just go, be weird, and take your picture. The actual address is 350 W Burnside St in case you can’t find it (it’s right behind Dante’s).

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

  • Tilikum Crossing: Have more time and looking for a scenic leisurely walk over the river? Head to Tilikum Crossing, also known as the “bridge of the people”, a .35 mile pedestrian, bike, and light rail bridge with unparalleled views of the Willamette River. Smart, right? Why don’t more cities have this (bridges that ban cars that is)? You can easily do this walk back and forth in under an hour. I reckon it’d be even more dramatic and scenic at night with all the city lights shining down on the river! Be sure to look out for the submarine near OSMI!

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

→ Read Next: 3 Perfect Days in Portland

Where (and what) to eat in Portland (my favorites):

  • Pok Pok: order the Vietnamese fish sauce wings
  • Blue Star Donuts: just do it, more than once (calories don’t count on vacation)
  • Coffee at Stumptown: grab some at the airport if you don’t have time
  • Salt and Straw ice cream: try some of their wacky flavors, changing all the time!
  • Abyssinian Kitchen: some of the tastiest Ethiopian food around
  • Katchka (Russian): try the herring under a fur coat, Siberian dumplings, lamb with rice, and cauliflower schnitzel (all super tasty)
  • Pine State Biscuits: I’m drooling just thinking about my breakfast
  • Fried Egg, I’m in Love: the best egg sandwiches in Portland, in my opinion
  • Tov Coffee: located in a converted school bus; get “the mint thing”, it’s orgasmic
  • Voodoo Donut: a Portland must-stop, even if everyone says Blue Star is better

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

Sleep: Portland (I’ve been lucky enough to stay with friends/family when visiting the area, but I’ve heard fantastic things about Ace Hotel Portland , Jupiter Hotel , Kimpton Hotel Monaco , and Stay Pineapple at Hotel Rose . Browse all hotels in Portland here .

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

Stop #2: Multnomah Falls and the Columbia River Gorge (1 day)

Distance: 30 miles to Multnomah Falls | Driving time: 45 minutes + driving through the Gorge

It’s time to grab those wheels (hint: car rental) and make our way towards our first official stop on this Oregon road trip, Multnomah Falls!

Being the tallest waterfall in all of Oregon state, a stop at Multnomah Falls really should be on any Oregon road trip itinerary, no matter how long or short. Looking up at the 600+ foot tall roaring cascade of icy water is awe-inspiring to say the least! It’s actually the most visited natural recreation site in the Pacific Northwest (whoaaa Nelly), so be prepared to share the views with 34,534 of your closest Portland-loving friends if you come after 10am. Visit before 9am and you’ll have the place almost to yourselves, season dependent.

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

Once Multnomah Falls is outta the way (and as noted earlier, head here early due to the crowds that arrive by 9/10am), continue on your waterfall-finding journey – there’s dozens upon dozens (!!!) of them in the Columbia River Gorge. The Gorge is essentially a canyon of the Columbia River, stretching more than 80 miles and up to 4,000 feet deep, and is kinda a divide between Washington and Oregon. With stunning vistas and enough waterfalls to last a lifetime, you’ll want to carve out at least half a day to explore.

Note that trails close on occasion due to wildfires, so you’ll want to make sure access is available before you set off on any hike. I’ve heard Horsetail Falls, Latourell Falls (it’s a few minutes before Multnomah, but go afterwards to beat the rush at Multnomah), and Wahkeena Falls are spectacular – but all were closed during my June 2018 visit due to the horrific fire in 2017.   Check for possible trail closures here .

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

Note that it’s about 45 minutes from Multnomah Falls to the town of Hood River, which is a good place to base yourself for the night. If you’re exploring other waterfalls in the Gorge, you’ll be even closer to Hood River.

Sleep: Hood River (Check out the Hampton Inn & Suites Hood River and the Best Western Plus Hood River – both great options). Browse all hotels near Hood River here.

Stop #3: Hood River and Mt. Hood (1 day)

Psst – if you’re really pressed for time you can combine stop #2 and #3 into one long day. It’s definitely doable, it’ll just be a little rushed. Do note that if you plan on doing some hiking, you’ll probably wanna split up the days, but your call! I visited everything in one day, but wasn’t able to do all the hiking I wanted due to the trail closures as mentioned above.

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

Distance: 47 miles to Timberline Lodge | Driving time: 1hr

Next up, Hood River, but first, a short pit stop at Rowena Crest . Sure, it’s about 25 minutes outta the way, but most definitely worth it for that instashot (I’m sure you’ve seen it somewhere – haha)! So what is it about this place that makes it rather popular?! Yes, it’s technically just a bend in the road but the surrounding scenery makes it a worthwhile stop.

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

This iconic horseshoe curve is actually one of the most photographed roads in all of Oregon! It does get pretty windy up here, so if you’re planning on taking that insta-photo, please be extra extra careful! Note that you’ll need to hoist yourself up and over the railing if you want more than just shoes in your shot (I was too much of a chicken to do so).

On your way to Mt. Hood, you’ll most likely wanna stop in Hood River for some lunch. My suggestion – Solstice Wood Fire Cafe for, you guessed it, some wood-fired pizza. Stretch those legs and go for a walk along the Hood River Waterfront for some great views of the area as well!

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

Additional pit stop: Hood River Lavender Farm ! An absolute must-stop for anyone who’s even a little bit lavender obsessed. Not only can you wander around the whole place smelling the sweet smells, but for $5, you can pick your own lavender to tie up and bring home! The place was smaller than I had expected, but there’s tons and tons of lavender bushes so it doesn’t even matter. Be extra careful when picking, as there’s lots of bees!

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

Be sure to look inside the gift shop for lavender jams/jellies, soaps, etc. If you come on a clear day you can even see Mt. Hood in the distance! FYI: Lavender picking season is from April/May to November, with peak bloom being July-August.

Wanna brag to your friends about finding the best views of Mt. Hood? Head to Trillium Lake , where the mountain literally reflects in the water and creates the most peaceful setting. What’s better than a mountain reflection in a jazzy blue lake? Not much! On a clear day, you’ll find Mt. Hood perfectly reflected in the water. Worth the short photo stop for sure! You can also walk around the lake for additional views as well, but we wanted to make it back by dinner so skipped the almost-2-mile loop trail. I want to visit during sunrise or sunset next time!

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

End this long day at Timberline , a mountain lodge right at the base of Mt. Hood, where you can watch the skiers summer ski and grab a bite to eat (if you’re so inclined). You of course can spend the night here if you’re planning on actually using the mountain for skiing or snowboarding (be sure to make reservations in advance), but we were just observers for the day.

Sleep in Mt Hood : Timberline Lodge if you’re feelin’ fancy, or check out Best Western Mt. Hood Inn or Collins Lake Resort for budget options in the area.

Stop #4 ( optional ): Silver Falls State Park (1 day)

(adds an extra 2-3 hours of driving time)

Distance : 94 miles to Silver Falls State Park | Driving time : 2hr plus traffic

→ Note that it’s more than possible to visit Silver Falls State Park as a day trip from Portland, so if you wanna do that and tack on a day to your Portland stop, feel free! → That’s what I did! It’s actually only about 1 hour, 15 minutes south of Portland, so if you prefer staying in the city and switching hotels one less time, a day trip to Silver Falls from Portland may be your best bet!

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

If the waterfall at Multnomah wasn’t enough for you, or you’re just a waterfall fanatic like myself, make the 2-3 hour detour to Silver Falls State Park. (Psst – I actually found the waterfall at Silver Falls State Park even more spectacular than those on the Columbia River Gorge). There are numerous trails available, with the easiest of them leading to the most impressive waterfall in the park – South Falls. You can even go behind some of them! Definitely reminded me of the some of the waterfalls I saw in Iceland!

If you’re looking for a longer hike, trek the entire 9 miles and you’ll be rewarded with 10 waterfalls (yes, 10!). Where else can you see 10 waterfalls on one hike?! We hiked about 3 miles or so and saw two waterfalls.

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

People actually call it the “crown jewel” of the Oregon State Parks system – you’ll quickly understand why after your first visit! I mean, who doesn’t appreciate a leisurely walk the rainforest (Oregon’s only one actually!)

Sleep : Browse all hotels near Silver Falls State Park here.

Stop #5: Smith Rock State Park (½ – 1 day)

Drive: 3 hours to Smith Rock State Park from Silver Falls State Park -or- 2 hours from Timberline

Located roughly 30 minutes north of Bend (next up on this Oregon road trip itinerary) in central Oregon’s High Desert (riiiight off the highway I might add), this is a spot you’d be absolutely mistaken to miss, no matter the weather. With scenic views of deep river canyons and ample hiking opportunities, Smith Rock is any outdoor-lovers dream. If you’re up for a workout on tons of switchbacks, head up to Misery Ridge for dramatic views of the entire canyon and nearby rock formations. This spot is a mecca for rock climbers, and even if you don’t subject yourself to Misery Ridge (it is called Misery Ridge for a reason), you can still spot them from the canyon floor.

Things to do in Bend, Oregon: A Wintery Guide to the City and Surrounding Areas (including where to stay, how to get around, where to eat, and lots more!)

we visited in winter, hence the reason we’re bundling up (obv)

Psst: if you’re an alpaca fanatic like I am (guilty!), be sure to check out Crescent Moon Ranch located in Terrebonne (right near Smith Rock State Park). make sure to head into the visitor’s lounge to pick up some alpaca food to feed the little guys and check out all the goods made from their soft, luxurious fleece. Wool sweaters, wool socks, wool stuffed animals, and oh so much more – it’s all there.

Sleep: near Smith Rock ( Sleep Inn & Suites Redmond and Best Western Plus Rama Inn are viable options) or in the areas of Mitchell / Prineville near the Painted Hills (depends if you wanna do more driving today)

Stop #6 ( optional ): Painted Hills and surrounding areas (1 day)

This minor detour to Painted Hills will take you roughly an hour and 45 minutes outta the way, but hey, you might as well see a lot of the state on this Oregon road trip. And plus, it’s one of the Seven Wonders of Oregon, so you kinda gotta see it.

The Painted Hills are just that – full of hills of a whole myriad of different colored soils, including yellows, golds, blacks, and reds. Top Tip: these different colors are best viewed in the late afternoon (the claystones appear different dependent on light and moisture).

But don’t leave just yet – the Painted Hills are just one of three units that make up the John Day Fossil Beds. You’ll find mars-like landscapes at the Clarno Unit, and fossils of plants and animals at the Sheep Rock Unit (which make up 55 million years of evolution with a giant collection of 40,000 fossils). And no, I didn’t exaggerate those numbers. It’s the real deal over in these parts! All of these three units have short trails to dramatic viewpoints of colorful rock formations – you could easily spend all day here. Note that the three units are roughly 1 hour away from each other, so you’ll need to account for some extra driving should you want to visit two or all three.

→ Important: If you’re staying after dark to watch the sunset (highly recommended), be extra careful when driving to your accommodations at night. There’s lots of wildlife out and about near the roads (deer, elk, etc).

Note that today’s kinda a lot of driving if you decide to see Smith Rock and the Painted Hills in one day, so you may want to consider sleeping in Mitchell near the Painted Hills (30 min drive) and driving to Bend the next morning. If you wanna get a head start the drive to Bend, sleep in Prineville (roughly 1 hr, 15 minutes from the Painted Hills and on the way to Bend).

Sleep : Bend at LOGE Entrada Bend (where I stayed and brand spankin-new) or The Oxford Hotel (another top-notch option recommended by a couple we met on our Craft Beverage Tour).   Browse all hotels in Bend here . (or Mitchell / Prineville near the Painted Hills)

Stop #7: Bend (2-3 days)

Drive: 2 hours to Bend from the Painted Hills

Located between the snow-covered peaks of the Cascade Mountains and the high desert plateaus of Central Oregon, Bend really has it all, and then some. Because of its prime location for outdoor activities (think hiking, biking, river sports, etc), you’ll find a ton of sporty enthusiasts living the rugged lifestyle.

Bend is basically an adults playground. And the town is super cute, too, with a whole slew of mouthwatering restaurants and cafes to indulge in!

Things to do in Bend, Oregon: A Wintery Guide to the City and Surrounding Areas (including where to stay, how to get around, where to eat, and lots more!)

As noted above, we visited Bend in it’s snowy winter months , and have yet to experience the area in all it’s warm-weather summer-glory. We fully enjoyed our time in Bend covered in snow, and went snowshoeing, took a craft beverage tour, and ate everything in sight (for real).

However, since I have a feeling you’ll be planning this Oregon road trip for a warmer month, I’ve compiled some of the best things to do in Bend sans piles and piles of snow. I have a few friends and cousins who frequent the area quite often (they’re Bend-obsessed), so I got some recommendations from them for you to enjoy.

Since Bend is sooo well known for its craft beers, you can’t leave town without taking part in the fun for at least a little while. The city is actually known as Beer Town USA, and has more breweries per capita than any other city in Oregon. Craft beverage tours like the Bend Ale Trail or the Local Pour Tour with Wanderlust Tours are especially popular to sample local sips.

Things to do in Bend, Oregon: A Wintery Guide to the City and Surrounding Areas (including where to stay, how to get around, where to eat, and lots more!)

We loved the mixture of the Local Pour Tour, visiting a local cidery, kombucha tap room, a whisky distillery, and of course a brewery. There’s even a non-alcoholic beer brewed for pups! Crazy, right?! They do love their beer over in Bend! If you’re a beer fanatic as well, you may want to schedule your trip to Bend during one of it’s many annual beer celebrations, including Central Oregon Beer Week, Bend BrewFest, or Bend Oktoberfest (among many, many more).

Things to do in Bend, Oregon: A Wintery Guide to the City and Surrounding Areas (including where to stay, how to get around, where to eat, and lots more!)

Alternatively, simply wander around the Old Mill District and Downtown Bend, which have tons of places to eat, stroll, or shop.

Outdoor lovers will also find tons to do here. During the summer, book a kayaking or canoeing expedition on the Cascade Lakes or the Deschutes River with Wanderlust Tours, who we actually went snowshoeing with in the winter and LOVED!

You can also enjoy the outdoors on foot or by bike, and you’ll see tons of people out on the trails on warm, sunny days. The Pilot Butte Trail is a popular hiking trail in Bend that takes you to the top of an extinct volcano (yup, I said volcano alright), with thrilling views of the surrounding Cascade Mountains nearby. It’s a beautiful, scenic trail for beginners and seasoned hikers alike. For bikers, you can’t beat the Deschutes River Trail, which extends over 12 miles and borders the Deschutes River, winding through canyons and beautiful green forests along the way.

Things to do in Bend, Oregon: A Wintery Guide to the City and Surrounding Areas (including where to stay, how to get around, where to eat, and lots more!)

what you can expect Bend to look like in the winter (that snow, swoon)

And if you’re looking to amp up your photography skills, book yourself a private lesson with Toni from Bend Photo Tours. She was oh so patient with me and answered all my silly (and quite embarrassing) questions without batting an eye. Next time I’m there I’m hoping the weather conditions are sufficient for some night-sky photography!

→ Read Next: A Snowy Weekend Trip to Bend, Oregon

Sleep: Bend at LOGE Entrada Bend (where I stayed and brand spankin-new) or The Oxford Hotel (another top-notch option recommended by a couple we met on our Craft Beverage Tour).   Browse all hotels in Bend here .

Stop #8: Crater Lake National Park (2 days)

Drive: 2 hours, 30 minutes to Crater Lake National Park from Bend

Crater Lake National Park has got to be one of the most mesmerizing places I’ve been to date, and thankfully, it’s up next on this Oregon road trip. With its calm dazzling blue waters, scenic highways, and super starry night skies, you can be sure you’ll never forget your visit to Crater Lake. And that’s a promise!

Heading to Oregon and wondering what all the things to do in Crater Lake are?! Click through for the best hikes, best viewpoints, where to stay, and what to eat - exactly what you need to plan your own visit to Crater Lake!

Some quick facts:

  • Crater Lake is currently the 10th-deepest lake in the world, with a maximum depth of almost 600 meters (1,949 feet). It’s also the deepest lake in the USA!
  • The magnificent intense blue color of Crater Lake is primarily due to it’s great, great depth, and remarkable clarity. The waters stay so clear since the lake has no other bodies of water flowing into it, meaning little-to-no pollution!  

Heading to Oregon and wondering what all the things to do in Crater Lake are?! Click through for the best hikes, best viewpoints, where to stay, and what to eat - exactly what you need to plan your own visit to Crater Lake!

We spent most of our time hiking, but there’s lot more to do at the National Park if hiking isn’t your jam. Revel in the views from Rim Drive’s multitude of lookout points, get some fancy drinks and/or a dessert at Crater Lake Lodge, take a boat cruise to Wizard Island, and even go for a swim (if you dare to step foot in the chilly waters)!

Heading to Oregon and wondering what all the things to do in Crater Lake are?! Click through for the best hikes, best viewpoints, where to stay, and what to eat - exactly what you need to plan your own visit to Crater Lake!

Although the park is open every single day of the year, many of the park’s roads, trails, and facilities are closed seasonally due to snow, which usually do not reopen until summer (June/July). If you want to ensure you’ll be able to drive around the perimeter of the lake (Rim Drive), schedule your trip for late July, August, or September. These also happen to be the most popular times to visit Crater Lake, but don’t fret – the park is rather large so you’ll still be able to find your own spots of peace and solitude.  

Heading to Oregon and wondering what all the things to do in Crater Lake are?! Click through for the best hikes, best viewpoints, where to stay, and what to eat - exactly what you need to plan your own visit to Crater Lake!

Sleep : Melita’s Crater Lake Lodge nearby Crater Lake (or you can head right to Ashland if you prefer). Browse all hotels near Crater Lake National Park here.

Stop #9: Ashland (1 day) – OPTIONAL

Drive: 2 hours to Ashland from Crater Lake National Park

Get one last look at Crater Lake, then hit the road; it’s time to make our way to Ashland, one of southern Oregon’s hot spots and loved by all.

Ashland is a classic Pacific Northwest hippie town with a love for nature, beer, and admittedly, all things weird. Here, you can find a very alternative vibe, with tons of green, vegan health shops, locally-brewed beers, and tons of places where you can get in touch with the quirky and downright strange personality of the place.

It’s not everywhere that you can watch Shakespeare, drink Sriracha flavored beer, and go to a paranormal activity hotspot in just one day. But in Ashland, you can do all this and more! Told you it was weird.

Speaking of Shakespeare, The Oregon Shakespeare Festival (OSF) is a must-see here, with regular shows at the Green Show, a performance venue and courtyard that’s frequented by visitors and locals alike. But if you’re not a fan of Shakespeare himself (say what?!), you can see other productions the group puts on, like Hairspray and Alice in Wonderland. The OSF shows usually happen during the summer, and if you choose to go to a classic Shakespeare show, don’t miss the ones at the Allen Elizabethan Theatre.

Aside from Shakespeare, there are tons of other weird and wacky things to do in Ashland. Beer lovers can find the strangest and most unique beers at the Caldera Brewing Tap House, a local favorite that made waves with its Sriracha Stout beer. You can also visit the Oregon Vortex, which is a weirdly spiritual spot known for paranormal activity and other strange happenings located about 30 minutes from town. And of course, don’t forget to enjoy the beautiful nature in the area, especially in the fall, when the leaves turn all kinds of beautiful colors.

Technically , if you wanna save a bit of driving and don’t have all the time in the world, you may choose to cut Ashland out of your Oregon itinerary. Your call, but I think it’s worth at least a day or so.

Sleep: Bard’s Inn Ashland . Browse all hotels in Ashland here.

Stop #10: Coos Bay // Southern Oregon Coast (1-2 days)

Drive: 3 hours, 15 minutes from Ashland to Coos Bay

It’s finally time to get this Oregon coast road trip itinerary underway! The drive from Ashland and Crater Lake will essentially take the same amount of time, so there’s no absolute NEED to visit Ashland if you’re pressed on time.  If you’re coming from either one, you have two options – the long way (~5 hour drive with more exploration of the southern Oregon coast), or the shorter way (3 and a half hours cutting straight to Coos Bay from Ashland/Crater Lake). I suggest opting for the short route as in my opinion, you won’t be missing out on too much by skipping the southern coast below (as Coos Bay is one of most scenic areas on the Oregon Coast)– but obviously, your choice!

San Francisco to Seattle Road Trip Itinerary: COMPLETE road trip with all stops, where to stay, and top things to do from San Francisco to Seattle (national parks, stunning lakes, best wine, etc)!

Coos Bay is home to the Cape Arago Beach Loop, which is where I’d spend the rest of the day.

On this driving/exploring/sightseeing loop, you’ll venture into three Oregon State Parks, watch a ton of seals and sea lions play, as well as stop at numerous breathtaking vantage points. The drive is not super long, but you’ll definitely want the better portion of the day to stop and soak it all in!

A few must-see stops: 1) Bastendorff Beach (say goodbye to crowds and hello to oh so much natural beauty), 2) Sunset Bay State Park (those towering sea cliffs sure are something, especially with the beautiful sandy beaches and amazing tide pool explorations), 3) Cape Arago Lighthouse Viewpoint (you unfortunately can’t view the inside but you can get fantastic views from here), 4) Shore Acres State Park and Botanical Gardens (tons and tons of blooms), 5) Simpson Beach (look out for the migrating whales and hundreds of seals and sea lions), 6) Shell Island (breeding and rest areas for seabirds and Marine mammals), and finally 7) Cape Arago State Park.

Sleep in Coos Bay : Browse all hotels near Coos Bay here.

Stop #11: Newport, Tillamook, and Cannon Beach (2 days)

Next up on this Oregon coast road trip → making the way back up north to Cannon Beach!

Prepare yourself as today’s primarily a driving day, but don’t worry, there’s tons of scenic stops along the way. Think scenic seaside towns, sand dunes, spectacular lighthouses, and cheese! Yes, cheese! Because who isn’t fascinated by cheese?

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

Sure, California’s Highway One surely steals the show when it comes to coastal road trips, but Oregon’s coast is one for the bucket list as well! With quiet seaside coves, bustling beach towns, and secluded hideaways, you won’t want to miss the beauty that is Oregon.

A few recommended stops between Coos Bay and Cannon Beach, where we’ll be ending the drive today. If you’re not pressed on time you can easily spread these activities/stops out over two days.

  • Oregon Dunes National Recreation Area: Wind-sculpted sand dunes for days (literally, miles and miles and miles). This NRA is actually one of the largest expanses of temperate coastal sand dunes in the world, so yea, I wasn’t kidding when I said Oregon’s coastline is on par with California’s .  You can even take a buggy or ATV tour of the dunes!
  • Haceta Head Lighthouse : The first of numerous lighthouses on our list, and this one just happens to be the brightest light on the Oregon coast and most photographed in the whole state. To say it’s simply stunning is a huge understatement.
  • Cape Perpetua: Don’t miss the Spouting Horn, an exploding salt water geyser, and Thor’s Well, a gaping pit with violent waves crashing in every direction that ultimately fall into a hole, just as weird and wonderful as it sounds.
  • Nye Beach: The perfect stop for a late lunch, depending on how much exploring/sand-duning you did earlier. This is also a great place to spend the night if you’ll be splitting the drive from Coos Bay to Cannon Beach into two days.
  • Yaquina Head Light: Being the tallest lighthouse on the Oregon Coast, you can’t miss this towering beauty
  • Devils Punchbowl State Reserve: This is a popular whale watching site and displays an intriguing geology. Also, as the name suggests, there’s a hollow rock formation shaped like a huge punch bowl. Better yet, go at sunset if you want to see something spectacular.
  • Tillamook Cheese Factory: Who could resist some fine, fine creamy cheese samples? Not I, that’s for sure! If you’re not familiar with the brand, Tillamook is a leading cheese provider in the area, who aims to connect farmers with everyday food lovers (hi!) with cheese and ice cream. Don’t miss the tour.
  • Cannon Beach: Phew, made it (finally)! HAYSTACK ROCK, enough said.

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

Finally, the last official stop on this Oregon coast road trip, the one and only Cannon Beach. Here at Cannon Beach, you’ll find the famous and ever-so-popular Haystack Rock (it’s a sight to be seen).

No matter where you stand, you’ll see it (I promise), as it towers 235 feet over the beach. If you can, plan your visit during low tide so you’re able to walk right up to Haystack Rock to search for sea creatures (crabs, sea anemone, mussels, and snails). Check here to see when the tide is at its lowest. Check out Pelican Brewing Company should you get hungry (the fish tacos were absolutely bomb).

Sleep: Hallmark Resort and Spa Cannon Beach or Surfsand Resort if you’re feeling fancy, or Hidden Villa Cottages for a less expensive room. Note that many of the hotels are quite expensive in Cannon Beach, so expect to pay at least $250 a night or so.

Thankfully, you’ve only got about an hour and a half drive west back to the city of Portland to complete this full Oregon road trip. Choose to drive back after your first night in Cannon Beach, or the morning after your second.

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

End: Portland → Phew, you made it back! Grab some Stumptown Coffee on your way home!

Are you visiting the state soon? What are you most excited about on this Oregon road trip itinerary!?

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April 5, 2024 at 8:41 am

Sharp photos! Bend is definitely vibrant in the summer. You should make the trip. Be sure to check out Galveston and the oldmill district =)

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how to travel to oregon

The Complete Oregon Road Trip Itinerary (50 Stops & 4 Unique Routes!)

Post Summary: The Ultimate Oregon Road Trip Itinerary According To A PNW Local

Oregon. That magical spot in the corner of the United States where roaring waterfalls, epic coastlines, and mysteries in the forest all thrive next to each other. 

It’s an incredible place that requires the guidance of PNW experts (that’s us!) to divulge all the best stops in the state. We’ve been exploring Oregon for years , so you can count on us to provide well-rounded tips to give you the best experience!

In this post, we’re sharing the most epic Oregon road trip route , including our favorite stops and custom trips of 2-weeks, 10-days, and 1-week to cater to your specific needs. Scroll all the way to the bottom to find a free Oregon road trip itinerary download , too!

Okay, enough talking, let’s get exploring!

how to travel to oregon

The Ultimate Oregon Road Trip Itinerary (Exactly Where To Find The Best Spots!)

First of all, where is oregon.

Oregon is located in a region called the Pacific Northwest , which is located in the northwest corner of the contiguous United States.

Fixed between its northern neighbor, Washington , and its southern neighbor, Northern California , Oregon is a unique mix of giant redwood trees, raging waterfalls, high desert, and beautiful coastal wilderness.

It’s got a little bit of everything , which is why taking an Oregon road trip will probably be the most incredible thing you will do this year!

Here’s a little bit about Oregon to start…

Oregon is broken down into seven distinct regions, each with its own unique spin on Oregon culture and iconic destinations . Here’s a breakdown of what you might expect from each:

  • The Oregon Coast: 363 miles of accessible beaches, historic lighthouses, sea stacks, and gorgeous little Oregon beach towns . 
  • Central Oregon: A High Desert escape including popular spots like Sisters, Bend, and Smith Rock State Park . 
  • Eastern Oregon : Lonely vast desert with incredible geological features scattered across the area. Known for the Alvord Desert, Pendleton, and the Painted Hills. 
  • Portland Region: The urban center for creatives, makers, and foodies. Known for its epic food culture, bridges, and accessibility to nature.
  • Mt. Hood & The Columbia River Gorge: Home to the highest mountain in Oregon (Mt Hood), and some of the most famous Oregon waterfalls like Multnomah Falls. 
  • Southern Oregon: Home to Crater Lake National Park, this region also boasts adventurous caves, gorgeous forests, and hidden hot springs (Umpqua Hot Springs). 
  • The Willamette Valley: Known for its amazing wine, tulips, and orchards, this farming community is a hub for a perfect weekend getaway.

how to travel to oregon

Great…So Where Do I Start My Oregon Road Trip?

The easiest place to start your Oregon road trip is in Portland . This is the biggest city, where you will find the most options for car rentals, flights into the state ( Portland International Airport – PDX ), and stores to pick up any last-minute supplies.

Our Oregon road trip itinerary has you starting in Portland and heading east, but you can always fit the route to suit your own needs and desires! Keep scrolling to see all the stops so you can make your decision.

How Do I Get Around On My Oregon Road Trip?

Emily Mandagie driving the Oregon Coast Highway 101

The easiest way to get around on an Oregon trip is to drive in a car . It’s unreasonable to believe that you can fly from place to place. The biggest major airport is in Portland (PDX) and the rest are smaller local airports.

It’s easiest to get around Oregon in a car , and we highly suggest this mode of transportation! If you are hoping to do some camping along the way, we recommend checking out the company Outdoorsy to rent a campervan . It’s like having your transportation AND accommodations all in one place.

Outdoorsy does local recreational vehicle rentals (kind of like Airbnb but for cars!) so you can travel around Oregon in style with a cool vintage VW bus or cute teardrop trailer!

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Where Do I Stay During My Oregon Road Trip?

The good thing about Oregon road trips is that they are completely customizable! You can stay at some of the coolest lodges and hotels in Oregon, explore backcountry roads for camping, or do a little mix of both!

Finding Epic Campsites in Oregon: There are so many amazing campsites in Oregon that the topic requires its own blog post! However, one of our most coveted tools for finding the best camping spots is through The Dyrt . The Dyrt is a campground finding app , and one of the best ones we’ve used! It’s got great reviews with photos, offline maps, road trip routing tools, and more! Our readers get to try it free for 30-days by using our code Mandagies !

Our favorite lodges & resorts in Oregon: Some amazing accommodations stand out among the others, and we think that some of these places deserve their own recognition! Here are some of our favorite lodges in Oregon that we recommend checking out!

FivePine Lodge – Sisters, OR (Central) Bay Point Landing – Coos Bay, OR (Southern Coast) Headlands Lodge – Pacific City, OR (Northern Coast) The Independence Hotel – Willamette Valley (Northwest/Central ORegon)

how to travel to oregon

The Mega Oregon Road Trip Itinerary (All The Best Stop In Oregon)

This two week Oregon road trip will bring you to all the best spots!

Stop 1: Portland, Oregon

Before departing the city, spend some time visiting Portland’s coolest locations! Some of the most popular outdoor places to visit in the city include the Portland Rose Garden, Washington Park, the Pittock Mansion (with its view of the city!), and Forest Park.

Grab a bite to eat at one of the several food truck communities around town. Click here to locate all the food truck pods around Portland!

From here, make sure to stock up with snacks at your favorite grocery store, fill up with gas, and hit the road!

how to travel to oregon

Stop 2: Columbia River Gorge Scenic Byway

Begin your Oregon road trip in Portland and head to Interstate 84 East to start your Columbia River Gorge Scenic Drive . This is a great start to any Oregon road trip itinerary for its iconic stops like Multnomah Falls, Latourell Falls, and Bridal Veil Falls. 

If you want to go hiking in this area, consider Wahclella Falls Trail (only 1.9-miles long) or Munra Point Trail for incredible panoramic views.

To spend more time checking out cool waterfalls in Oregon , consider taking the Historic Columbia River Highway (that parallels I-84), which provides easy access to many of them. Don’t forget to drive a little farther than Hood River to check out Rowena Crest , that famous hairpin road!

Note: The Eagle Creek Fire of 2017 devastated much of this area, and hikes/waterfall trails are slowly opening after restoration efforts. Click here to be updated on real-time trail openings in the Columbia River Gorge . 

Extra Stops Between Portland and Hood River:

  • Vista House – A museum, observatory, and rest stop
  • Bridge of the Gods – Many of the Pacific Crest Trail Hikers cross here!
  • Beacon Rock State Park (on the Washington side)
  • More than 25 Columbia River Gorge waterfalls to see!

how to travel to oregon

Stop 3: Hood River, Oregon

Hood River, Oregon is the perfect place to stay after a day of planning fun things to do in the Columbia River Gorge ! Placed conveniently on the river’s edge, there is easy access to Mount Hood directly south, water activities like windsurfing , and Washington waterfalls right across the river in the Gifford-Pinchot National Forest to the north.

If you want a little more adventure, consider crossing the toll bridge ($2) to Washington and venturing on nearby trails to Falls Creek Falls , Panther Creek Falls, or Lower Lewis Falls.

Cool Places To Stay in Hood River, Oregon

Modern Townhome in White Salmon, WA (just across the river) MtAdamsView in Hood River (TONS of gorge and mountain views, sleeps 6) Best Western Plus in Hood River (great value, free breakfast)

how to travel to oregon

Stop 4: Mount Hood

Route your Oregon road trip from the river’s edge to the mountains, more specifically to all the cool things to do in Mount Hood !

Watch a sunrise at  Trillium Lake – one of the easiest lakes to reach on Mount Hood. On a clear day, you will be able to see the reflection of the picturesque Mount Hood beautifully framed in the distance! Other Mount Hood lakes include Frog Lake,  Lost Lake,  and  Mirror Lake –  each with their own unique reflection of the mountain. 

If you are interested in discovering some cool hiking trails around Mout Hood, consider  Ramona Falls trail. This gorgeous horsetail falls is hidden deep in the forest, but the payoff is huge once you see it with your own eyes. Care for a short waterfall hike for your Portland day trip? Consider  Tamanawas Falls , an easy 3.3-mile trail with a gorgeous view!

Want to challenge yourself? Here are some other longer hikes in the Mount Hood area.

  • Tom Dick and Harry  (9 miles out and back)
  • Bald Mountain  (6 miles out and back)
  • McNeil Point Trail  (9.6 miles out and back)

how to travel to oregon

Stop 5: The Painted Hills

After stopping at Mount Hood (overnight or just for a day trip) take the 3.5-hour drive from Mount Hood to the Painted Hills to catch a gorgeous sunset in the Oregon desert. 

The Painted Hills gets its name from the exposed layers of colorful soil that are revealed in the rolling hills of the John Day Fossil Beds . Make sure to stay on the boardwalks as you explore the Painted Hills. The hills are extremely fragile!

In the morning, return to the John Day Fossil Bed units and see the Painted Hills as the sun rises! This is a gorgeous time of day in the hills, and you’ll likely get it all to yourself in the early hours of the morning. 

Need a place to sleep? Consider these nearby campgrounds (or click here to discover FREE campsites nearby too! )

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Stop 6: Smith Rock State Park

From the Painted Hills through the Ochoco National Forest , take the 1.5-hour drive to Smith Rock State Park . Smith Rock is a hub for climbers , but there are several other things to do here, including hiking, biking, and taking photos!

To stretch your legs on this Oregon road trip, take the short but *very* steep Misery Ridge Trail . This 0.68-mile trail climbs 600 feet giving even the most experienced hiker a run for their money! The views at the top are worth it though, especially during sunrise or sunset!

Emily Mandagie biking in Sisters, Oregon - TheMandagies.com

Stop 7: Bend, Oregon

The city of Bend is an excellent stop on any good Oregon road trip! It’s an outdoor-loving town that connects Western Oregon and Eastern Oregon, making it a great pit stop to pick up last-minute gear, groceries, and maybe even tune ups for your car.

For a little relaxation from the road, grab a beer in town at any of the iconic stops on the Bend Ale Trail . If you are visiting in the summertime, floating the Deschutes River is a popular activity on a hot day. Make sure to bring your PFDs, water sandals, and a garbage bag!

In the morning, grab breakfast in Bend at The Sparrow Bakery, (their ocean rolls are famous!), and some to-go coffee at Spoken Moto and make some fun stops around Bend on your way south. Lava Island Falls and Lava River Cave are both easy and accessible places to see along your Oregon road trip route going out of town.

More adventures near Bend, Oregon

  • Hiking to Tumalo Falls (6.5 miles out-and-back)
  • Go backpacking in the Three Sisters Wilderness
  • Take a road trip detour on the Cascades Lake Highway

Read More: How to Spend 4 Days In Bend, Oregon

Eastern Oregon Road Trip Route - Leslie Gulch Stop

Oregon Road Trip Bonus Route – Eastern Oregon!

Psst…want to spend a lot more time in Eastern Oregon? Check out our Eastern Oregon Road Trip route right here !

From Bend, you have the option of extending your Oregon Road trip going east , or continue south and west towards the coast! Either option is great, it really just depends on how much time you have.

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Stop 8: Oregon Waterfalls

The drive from Bend to Crater Lake National Park is pretty short, about 1.5 hours. This gives you plenty of time to make some fun stops along the way , most notably, to waterfalls in Oregon !

For longer Oregon waterfall hikes, make your way west on Highway 58 for a fun hike at Salt Creek Falls and Diamond Creek Falls . Continue your drive south and divert north on Highway 138 for a stop at Watson Falls before making your way to the Crater Lake North Entrance. 

More Oregon Waterfalls Near The Area:

  • Proxy Falls (Highway 242 – North of Bend)
  • Chush Falls (Near Sisters, Oregon)
  • Dillon Falls
  • Benham Falls

Stop 9: Crater Lake National Park

Crater Lake National Park is one of the most iconic stops on an Oregon road trip, and the ONLY national park stop in the state. Spend sunset capturing the iconic Wizard Island on Crater Lake, and top it off by spending the night at the historic Crater Lake Lodge .

In the morning, spend an entire day hiking around Crater Lake on Watchman Peak Trail, Cleetwood Cove Trail, or Cloudcap Overlook.

At Crater Lake , you can spend the morning driving the Rim Drive , which takes about 2 hours to go all the way around. Hike to Plaikni Falls in the afternoon and in the evening watch the sunset at Garfield Peak or Sinnott Memorial Observation Station.

Emily Mandagie sitting in Hart Mountain Hot Springs in Eastern Oregon

Bonus Oregon Road Trip Stop: Oregon Hot Springs

Now, this is the part of your road trip route in Oregon where you can choose where you’d like to spend your time! You can opt to continue driving east to explore some of the famous Eastern Oregon hot springs . 

If you decided to check out some hot springs in Oregon , we highly suggest booking an overnight stay (Summer Lakes Hot Springs and Crystal Crane have lodging available!) or bringing your camping gear to find some free camping nearby . 

Here are some Oregon hot springs you should be checking out on this leg of your Oregon road trip itinerary:

  • Crystal Crane Hot Springs – Hot spring pond and private soaking tubs
  • Summer Lakes Hot Springs – Communal bathhouse
  • Hart Mountain Hot Springs – Structured underground pool and open springs, both natural
  • Have an extra day? Drive farther east and check out Alvord Hot Springs , and Willow Creek Hot Springs !

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Stop 10: Umpqua National Forest

Another iconic destination on your Oregon road trip is an adventure in Umpqua National Forest . You’ve probably seen pictures of those cliffside hot springs pools, or the rushing waterfall flanked by towering basalt cliffs. Well, these places are Umpqua Hot Springs and Toketee Falls !

Both places are easy to reach, each with a short hike to the final destination. Come with a national forest pass to hang in your car’s rearview mirror. You can pick one up at the Diamond Lake Ranger Station nearby if you need one. See the difference between Pacific Northwest forest passes here to find the correct one.

Leave No Trace Notes: Umpqua Hot Springs is notorious for garbage . Please pack out your trash, and consider taking other garbage with you, too. Hiking to the base of Toketee Falls is prohibited , no matter how many pictures you see of people doing so. It is possible to get cited for climbing down to the bottom, so don’t risk it!

Best Beaches on the Southern Oregon Coast - Natural Bridges

Stop 11: Southern Oregon Coast

Finally, the first ocean stop on your Oregon road trip!

The Southern Oregon Coast is arguably the most beautiful area of an Oregon road trip. If you love seaside cliffs, hidden coves, and gorgeous beaches, this is the place for you!

Spend some time exploring the 12 miles of protected coastline at Samuel H. Boardman Scenic Corridor . This part of your road trip in Oregon will take an entire day, between stops, viewpoints, and even a hike to a place called Secret Beach .

Finally, end your day in Gold Beach for the evening. Here, you can find tons of amenities, hotels, and beach rentals for a quiet and relaxing evening. Make sure to stop at our favorite beach, Myers Creek Beach to enjoy a beautiful Oregon coast picnic to end the day!

Read More: The 25 best beaches in Oregon (From North to South!)

how to travel to oregon

Stop 12: Central Oregon Coast

Central Oregon is full of adventurous destinations and unique curiosities. If you like thrills, try renting an ATV to ride across the Oregon Dunes, stretching 40 miles across the coastline.

You can also check out incredible places like Cape Perpetua , which is filled with churning coves, sea spouts, and lots of tide pools along the Oregon Coast .

Devil’s Punchbowl State Natural Area is another great place to explore, with a giant sea cave and surfing opportunities!

In the evening, splurge to go glamping and one of Coos Bay’s coolest spots – Bay Point Landing ! This luxury camping resort has plenty of pull-in sites for RVs and trailers. You can also rent a standalone cabin , airstream , or renovated RV of your own to enjoy upscale camping. The grounds have amenities like a pool, lounge room, upscale bathrooms, and a cute camp store.

Downtown Eugene 20x21 Mural Project - TheMandagies.com

Stop 13: Eugene, Oregon

If you wanted to go inland to explore the Cascade Mountains, this is the part of your Oregon road trip to make that decision! Drive away from the Oregon coast to go inland to Eugene, Oregon, and explore this upbeat college town.

But before leaving the coast, consider stopping by Heceta Head Lighthouse and Cape Perpetua for one last adventure by the water. The lighthouse can be seen up close with a short hike, which is incredible at sunrise and sunset!

Cape Perpetua is best explored during low tide, where you can access the many tide pools and curiosities that dot the shore. If you do come during high tide, don’t fret! You can see the waves push up through Thor’s Well for a dramatic display, and the Devil’s Churn to watch the waves crash around this small cove. 

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Stop 14: Willamette National Forest

Heading inland from Eugene, there are a ton of beautiful places to see in the Willamette National Forest . The first stop is Terwilliger Hot Springs (often called Cougar Hot Springs) for a lovely natural soak. Keep driving to choose a waterfall adventure – Proxy Falls , Sahalie and Koosah Falls , The Blue Pool , and Tamolitch Falls .

You’ll want to spend at least a full day in this area (or even go camping overnight!) because the trails here are packed with adventure! Keep driving on Highway 126 as it continues on Highway 22 north to Silver Falls State Park and Salem, Oregon to continue on your epic Oregon road trip.

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Stop 15: Salem and The Willamette Valley

If you like good food, you’re going to love this stop on your Oregon road trip. The Willamette Valley is full of wineries, farms, and beautiful vineyards! There are lots of options to enjoy farm-to-table dinners, wine tastings, and all-day experiences. Consider staying nearby at the Independence Hotel .

For a little adventure, head to Silver Falls State Park where you can hike the Trail of Ten Falls . This Oregon hike is exactly what its name entails – ten beautiful falls in an 8.7-mile trail. Come enjoy this condensed version of many iconic Oregon waterfalls all in one place!

how to travel to oregon

Stop 16: Northern Oregon Coast

Refueling in Salem, it’s time to get back to the coast! The final stops on your Oregon road trip include classic North Oregon Coast stops and beautiful Oregon beach towns , hikes, and plenty of dreamy overlooks.

Beginning in Cape Kiwanda , spend the day hiking up the sand dunes to watch the dory boats dock onshore and paragliders sail down to the beach. Make sure to stop and eat lunch at Pelican Brewing . They have incredible beer and pub food, with an outdoor patio overlooking Pacific City’s own Haystack Rock.

Continuing north to another iconic “Haystack Rock” (arguably the most popular one too) Cannon Beach is the best place to grab a coffee and take a walk along the beach. During low tide, you can get close to the rock and spot puffins in their natural habitat!

how to travel to oregon

If you want a little more adventure in your day, drive up to Ecola State Park to hike Crescent Beach Trail , the trail to Indian Sands, or Tillamook Rock Lighthouse Viewpoint. These lush Oregon Coast hikes are sure to leave you breathless!

Stay either at the Headlands Lodge in Pacific City , Oregon Coast Modern Cabin in Manzanita , or affordable hotels in Cannon Beach !

Peter Iredale Shipwrek at Fort Stevens State Park

Stop 17: Finish Your Oregon Road Trip Back to Portland, Oregon 

On your way back to Portland to finish your Oregon road trip, you can take the short way on Highway 26, or the long way through Astoria, Oregon, and heading back to the city on Highway 30.

The detour through Astoria won’t disappoint! Filled with great restaurants, antique and vintage shops, and lots of history, it’s a perfect final stop on the Oregon coast road trip section of your drive.

For outdoorsy activities, stop by Fort Steven’s State Park to check out the historic military installation, as well as the famous Peter Iredale shipwreck . For hiking, stay close to town and check out the Cathedral Tree Trail and the Astoria Column .

And you’ve done it! You’ve completed the coolest Oregon road trip to see all the best highlights, hikes, and iconic locations in the state.

how to travel to oregon

Oregon Road Trip Itinerary Examples

Below, we’re sharing some Oregon road trip itinerary examples to help you customize it exactly to fit your needs. For even more resources, we created this road trip itinerary in Oregon to print out and take on your journey!

(We’re running some email maintenance – this download will be back soon!)

Two Week Oregon Road Trip

See the detailed breakdown of our two-week Oregon road trip itinerary above!

10 Day Oregon Road Trip

You can see a lot with 10 days in Oregon! This route is a compressed version of our two-week road trip, with just a little less time in each spot but plenty of stops for an epic and interesting route!

  • Day 1: Portland to Hood River
  • Day 2: Hood River to Bend, Oregon
  • Day 3: Bend, Oregon to Crater Lake National Park
  • Day 4: Crater Lake to Umpqua National Forest
  • Day 5: Umpqua National Forest to Samuel H. Boardman
  • Day 6: Samuel H. Boardman to Coos Bay
  • Day 7: Coos Bay to Eugene, Oregon
  • Day 8: Eugene, Oregon to Salem, Oregon
  • Day 9: Salem, Oregon to Cannon Beach
  • Day 10: Cannon Beach to Portland, Oregon

One Week Oregon Road Trip

One week for an Oregon road trip will introduce you to Oregon’s vast and diverse landscape! From Crater Lake to Bend, Coos Bay to Cannon Beach, this route will bring you to some of the best of Oregon photography locations. 

  • Day 1: Portland to Hood River
  • Day 2: Hood River to Bend, Oregon
  • Day 3: Bend, Oregon to Crater Lake National Park
  • Day 4: Crater Lake to Samuel H. Boardman
  • Day 5: Samuel H. Boardman to Coos Bay
  • Day 6: Coos Bay to Cannon Beach
  • Day 7: Cannon Beach to Portland, OR

5 Day Oregon Road Trip

With 5 days in Oregon, you can see the highlights! This quick trip averages about 3-4 hours of driving per day, and takes you through mountains, by waterfalls, and meets up with some of the most scenic views along the Oregon Coast.

  • Day 1: Portland to Bend
  • Day 2: Bend to Eugene
  • Day 3: Eugene to Samuel H. Boardman
  • Day 4: Samuel H. Boardman to Yachats
  • Day 5: Yachats to Portland

Have you ever experienced an Oregon road trip? What Oregon itinerary is your favorite? Tell us in the comments below!

how to travel to oregon

Amazing! I know nothing about traveling all over the country, what a wonderful looking place to explore.

I’m really glad you liked our Oregon road trip route! I hope you et a change to travel across this beautiful state!

The Van Escape

The Epic Oregon Road Trip Itinerary

This Oregon Road Trip Itinerary will help you live an epic and fabulous adventure through this glorious Pacific Northwest state. Mountains, waterfalls, river gorges, dense forests, a fairy-tale coast, wineries, hot springs, wonderful cities, ghost towns, and the USA’s deepest lake. Oregon impresses with its attractiveness and variety of landscapes. We show you must-see stops and things to do. Oregon is also a picture-perfect state, so we tell you the best photo spots to catch its wild natural beauty. We give you also hints on where to stay and what to pack. So, check our Epic Oregon Road Trip Itinerary with lots of tips and photos to prepare for an adventure.

oregon road trip itinerary: photo collage with stunning scenery

Oregon Road Trip Itinerary – Introduction

We fell in love with Oregon on our first visit and have been to it several times. We admire this state because of its incredible beauty and variety. Moreover, we love to photograph waterfalls, mountains, covered bridges, and original architecture in Oregon.

My partner Chris and I developed this itinerary based on our experiences and insights. We show you the places you should not miss during the Oregon Road Trip. All photos presented in this article we took during our several Oregon road trips.

How many days do I need for the Oregon Road Trip?

Oregon is beautiful, so the longer the road trip you plan, the better. Our itinerary includes a 10-day Oregon road trip that begins and ends in Portland . A 10-day Oregon road trip will allow you to enjoy this state, see its greatest attractions, and take great photos.

But at the end of this article, you will find tips on what to add to your itinerary if you have 14 days . We also tell you how to shorten this plan if you only have 7 days to travel and want to see as many places in Oregon as possible.

Below, you will find our plan at a glance. Later, each day is described in detail with the itineraries, road suggestions, driving time, the most interesting stops, and attractions. We assure you that you fall in love with this state after seeing these places and want to return to Oregon.

The Epic Oregon Road Trip Itinerary Overview

Day 1. Arriving at Portland and exploring Portland. Day 2 . Driving to Mount Hood and hiking in the Mount Hood area. Day 3. Sightseeing of Shaniko Ghost Town and driving to Sisters. Day 4. Exploring Sisters and Bend – Willamette National Forest area. Day 5. Driving to Crater Lake National Park and Umpqua National Forest. Day 6. Exploring Crater Lake National Park. Day 7. Driving to Oregon Coast and Oregon Coast Road Trip. Day 8. Oregon Coast Rod Trip – exploring Oregon Coast. Day 9. Exploring Oregon Coast and return to Portland. Day 10. Exploring Portland and Columbia River Gorge/Multnomah Falls.

Crater lake national park in Oregon.

What Should You Know About Oregon Before You Go On A Road Trip?

  • Oregon is a state where you  refuel your car without leaving it . At the gas station, you are served by a gas station employee . Refueling by yourself in Oregon carries a fine of up to $500. It’s similar only in New Jersey. It is worth remembering this when planning your Oregon road trip. This rule does not only apply to motorcyclists.
  • There is  no sales tax in Oregon . Therefore, it is a state worth visiting, if only for shopping. Oregon is one of only five states (alongside New Hampshire, Montana, Delaware, and Alaska) where the price you see on the product is what you pay at the checkout. So, it’s worth shopping in Oregon. The best shopping in Portland.

What is the best time for Oregon Road Trip?

Oregon is attractive all year round. It all depends on your favorite outdoor activities and the way you travel. But this Oregon road trip itinerary is fully usable during the summer and fall months from May to the end of October.

Some of the recommended places to visit are inaccessible in winter due to closed roads. However, we tell you which roads are closed in winter so that you can also adapt your itinerary to the winter months.

Summer and Fall are also the best months for all our suggested activities. Pleasant weather enables longer hikes in the fresh air. The days are also long, so you will see more places and drive longer distances.

However, most tourists will certainly be in the high season in July and August. Therefore, if you are going during these months, we suggest that you start your sightseeing in the morning to avoid the crowds.

Oregon Road Trip Map

Please, take a paper map for your Oregon road trip. You will need it. Believe us, very often, there is no phone coverage, and you must use the traditional map. We love modern apps, but they have become useless in places like mountains, deep forests, and challenging hikes. So, a paper map is best when no cell service exists.

We use Benchmark Oregon Road & Recreation Atlas . It is very informative and detailed. Thanks to this atlas, our trips were more interesting, as we could quickly learn what was nearby and plan our route. It’s also a useful alternative to GPS maps when traveling.

Where to stay during the Oregon Road Trip?

It all depends on your needs, travel style, and budget. We traveled both by car and slept in lodges/hotels and by an RV, and stayed at campsites. Therefore,  we recommend specific lodging options for each day of the trip—only those we checked and were satisfied with—hotels and RV campgrounds for each location .

But no matter what you decide,  book your accommodation well in advance .

If you plan camping in Oregon, check our Car Camping Checklist.

What to pack for the Oregon Road Trip?

Our journey leads through the mountains, dense forests, waterfalls, hot springs, and heavenly beaches, so you should pack properly. Oregon’s climate is temperate but fairly humid, with frequent rainfall. The humidity is felt in the mountains and forests, so always be ready for rain.

Please check our detailed  Day Hiking Packing List  to see what to pack for hiking trails.

Furthermore, check our  Road Trip Packing List Essentials  to make your Oregon Road Trip safe and comfortable.

stunning Mt Hood and city of Portland view from the hill.

Day 1 Oregon Road Trip Itinerary: Arriving in Portland and exploring Portland

Arriving in portland.

Our Oregon road trip begins in the capital of the state – Portland. The city has an international airport, so it’s the most convenient way to get there. You can rent a car from the rental located at the airport.

Lodging in Portland

For this Oregon road trip itinerary, we recommend you book 2 nights in Portland – the first and the last . Of course, you can modify the plan to your needs.

During our few trips, we stayed in the  Courtyard by Marriott Portland City Center . We really enjoyed staying here. Our room was clean, and it had a lot of space, the service was great.

We also stayed in the  Mark Spencer Hotel , which is fabulous, in the city’s heart. But check below on the Deals finder the best offers.

During the last trip with the motorhome, we stopped at Portland Fairview RV Park .

Sightseeing Portland

Portland is a delightful city, so we’ve put together a detailed Portland Itinerary . What do we suggest you see during the day after your arrival? Start from Downtown Portland and the river waterfront loop. It’s a 2.6-mile loop that runs right along the Willamette.

There are 12 fabulous bridges over the Willamette River. If you have time, visit Portland Japanese Garden and go to the Pittock Mansion situated 1,000 feet above the city.

bridges in Portland by night.

Day 2 Oregon Road Trip Itinerary: Driving to Mount Hood and hiking in the Mount Hood area

Drive to timberline lodge & mount hood.

Take US-26 W and drive to the Mount Hood area. The drive will take you about 2 hours, and it is a scenic route.

Lodging in the Mt Hood area

We suggest 1 night in the Mount Hood area in this Oregon Road Trip Itinerary.

Timberline Lodge is a historic beauty hotel near the magnificent Mount Hood. Moreover, the psychological horror “The Shining” from 1980, directed by Stanley Kubrick, was shot at the Timberline Lodge. You can check our photos from this fabulous and thrilling filming location here. If you can, stay overnight at Timberline Lodge. If the place is busy, choose one of the nearby accommodations. Nearby are Best Western Mt. Hood Inn , The Mt. Hood Oregon Resort .

Hiking in the Mount Hood area

the view of Mount Hood area from Timberline lodge.

No matter where you stay for the night, head to Timberline Lodge and see this fabulous scenery. Moreover, they have great restaurants where you can have lunch or dinner. Finally, the Timberline Lodge parking lot provides access to many trails on the flanks of Mount Hood. So, you can choose one or two hikes in Mount Hood National Forest.

  • Mountaineer Trail Loop Hike is a great hike because there is such an easy road that goes so high on the mountain. The distance is 2.7 miles. The easiest hiking opportunity is to stroll in any direction you feel like.
  • Zigzag Overlook Hike is also easy to hike. The distance is 4.4 miles. You will see the alpine areas of Mount Hood’s south side. You’ll pass alpine and subalpine meadows to reach an overlook over the deeply gouged Zigzag River Canyon, with the craggy ramparts of Mount Hood above.
  • Paradise Park from Timberline Lodge Hike is a longer but fabulous hike. The distance is 12.1 miles, and it isn’t easy. Is a classic mountain trek. In addition to the mountain vistas and wildflowers, the route passes several waterfalls and offers unique views of the high country south and west of Mount Hood.

Day 3 Oregon Road Trip Itinerary: Sightseeing of Shaniko Ghost Town and driving to Sisters

Drive to shaniko ghost town and explore it.

From Mt Hood, take OR-216 and in Maupin, take Bakeoven Road. It’s about 77 miles and 1 hour 45 minutes driving to Shaniko. You need about 2-3 hours to explore Shaniko. From 1903 Shaniko gained the nickname “Wool Capital of the World.” 

You will find an old railway station, antique items, and wooden architecture from over 100 years ago. The town has an amazing history. You can read more about it and check more our photos in our post- Shaniko Ghost Town .

historic buildling of Shaniko Hotel.

Drive to Sisters

From Shaniko, take US-97 S and OR-126 W to Sisters. It’s 84 miles and about 1 hour and 40 minutes driving.

Sisters is a fabulous town, surrounded by mountains and forests. We detailed described its attractions in post Things to do in Sisters .

We also described interesting routes in the area there. Situated in the foothills of Oregon’s Cascade Range, Sisters and Bend are perfect for holidays. Moreover, it’s a great idea to spend here also winter vacation if you like skiing.

Lodging in Sisters or Bend

We suggest 2 nights at Sisters during your Oregon Road Trip. The area is fabulous. However, it might be difficult to stay overnight in the summer. Therefore it is also worth considering the nearby Bend. It’s about 25 minutes from Sisters. It is a larger city and has a well-developed accommodation and catering base. It’s worth visiting Bend for sure.

Sisters in Oregon.

Best Western   Sisters Oregon is our favorite one. It is a small, charming Ponderosa Lodge with 48 oversized guest rooms renovated in a country theme. Tasty breakfasts and friendly service. 

If you need RV camping, the best RV park in the area is  Bend / Sisters Garden RV Resort . But you have to  book it well in advance . It’s closest to the Sisters, located in a beautiful setting, and it’s hard to get a spot, especially in high season.

Hotel rates in Bend are much more affordable than in Sisters, so consider this place for optimizing your holiday budget.

Day 4 Oregon Road Trip Itinerary: Exploring Sisters and Bend – Willamette National Forest area

We suggest you actively explore the Willamette National Forest area on this day. Below are three of our favorite hikes. They are not long, so it is possible to make them in one day. Or you can choose the ones that suit you best. Prepare some more snacks and lunch.

Sunrise or early morning hike at Sparks Lake

Sparks Lake is 49 miles and an hour’s drive from Sisters. You have to drive through Bend. So, take US-20 E to Bend and turn onto Cascade Lakes National Scenic Byway. The scenery is breathtaking. If you like sunrises – they look fabulous in this place. But you can also go there during the day for a walk. This road may be closed in winter.

Sparks Lake near Sisters during sunrise.

Proxy Falls Hike & McKenzie Pass Scenic Byway

stunning cascade of waterfall during Proxy Falls Hike.

Proxy Falls, AKA Lower Proxy Falls, is a dazzling cascade waterfall hidden in the Three Sisters Wilderness. It’s near McKenzie Pass and McKenzie River in the Willamette National Forest. From Sisters, it is only 28 miles and approximately 50 minutes drive via OR-242 W. For more photos and tips, see our Proxy Falls Hike post . The best idea is to combine this hike with The McKenzie Pass-Santiam Pass Scenic Byway. Oregon Route 242, known as a portion of the McKenzie Highway, takes you on a journey through a land of contrasts. You’ll encounter lush forests, crystal-clear lakes, and lava fields on the west side of the Cascades. Stop at the  Dee Wright Observatory . In our opinion, Route 242 is one of the most scenics, so it’s a must in Oregon Road Trip Itinerary. This road is closed in winter.

Tamolitch Blue Pool Hike

Tamolitch Falls, also known as Blue Pool due to its amazing blue color of the water, is a popular hiking spot in  Willamette National Forest , Oregon. The deep turquoise and stunning clarity of the Blue Pool make this place unforgettable. The approximate hike time is 1 hour and 30 minutes one way. From Sisters stay on US-20 West. Then turn onto OR-126 E for 10.8 miles. Turn right at a sign for Trailbridge Campground/Blue Pool. You must cross a bridge and turn right onto gravel road NF-730. After about a third of a mile, park along the right side of the road.

Agnes Stabinska, the author, admiring the view of Tamolitch Blue Pool during Oregon road trip.

Day 5 Oregon Road Trip Itinerary: Driving to Crater Lake National Park via Umpqua Hot Springs

Saok in umpqua hot springs.

From Sisters is 115 miles and 2 hours 15 minutes driving via US-97 N to Crater Lake National Park . But we suggest you take a bit off course and soak into one of Oregon’s best hot springs – Umpqua Hot Springs.

Agnes Stabinska, the author is soaking in Umpqua Hot Springs in Oregon.

So if you like hot springs, take from Sisters US-97 S and OR-138 W to get to Umpqua Hot Springs. It’s 2 hours 45 min driving (143 miles). They are located in Umpqua National Forest. This set of 7 geothermal pools sits right on the edge of a rock face, spilling 108-degree water into the North Umpqua River below. The view is breathtaking. There is a short hike to get to the hot springs. It should take you 20 minutes to get to the pools. For more photos, hike & trailhead descriptions, hot springs etiquette, you can check in our Ultimate Guide to Umpqua Hot Springs in Oregon .

Driving to Crater Lake National Park and Lodging option in the area

The Oregon road trip itinerary would not be complete without a visit to a fairy-tale volcanic Crater Lake. You are less than an hour’s drive to Crater Lake National Park from the hot springs, depending on where you are staying. Try to reach the sunset because they are spectacular above Crater Lake. It is the only national park in Oregon. Moreover, it is the deepest lake in the USA with the clearest and bluest water in America. We prepared a detailed guide to this place with tips, so read Top Things To Do in Crater Lake National Park .

If you plan your Oregon road trip in May or the beginning of June, check the weather on the NPS website . Sometimes in May, there is still a lot of snow. You can visit the park, but some roads might be closed.

Lodging option

We suggest 2 nights at the Crater Lake NP area. Crater Lake Lodge   is a historical lodge inside the Park. Unfortunately, it’s not easy to book it. It’s pretty expensive. Moreover, it’s open only from May – September, filling up guests quickly.

But Chiloquin is only 8.5 miles from Crater Lake National Park, so check accommodation there. 

If you are looking for a campground Diamond Lake Resort & RV Park  is a great place to relax. It’s only 4 miles to Crater Lake park entrance, so the location is perfect. Book in advance.

But if you plan a winter trip, 1 night in Crater Lake should be enough because some roads and trails are closed. So, 1 day for sightseeing in winter will be optimal.

Sunset at Crater Lake and Crater Lake Rim Scenic Drive

Crater Lake looks great before and just after sunset. The light is the warmest then. The water surface is flickering. The historic  Crater Lake Rim Drive is a 33-mile (53-km) long road , which offers breathtaking and panoramic vistas of the lake, forests, and meadows. Along the way, there are 30 overlooks with ample car parking, which provide opportunities to stop for views, admire it, relax, taking photos.

stunning view of Crater Lake National Park during sunset.

Day 6 Oregon Road Trip Itinerary: Exploring Crater Lake National Park

Crater lake national park during sunny day.

On this day of the Oregon Road Trip Itinerary, we focus on exploring Crater Lake National Park’s beauty. If you can do it, get up for the sunrise. The view is worth your effort. Have a picnic at one of the viewpoints. Take one or two trails. We describe 7 Best Day Hikes in Crater Lake National Park  from easy to strenuous here . It’s worth visiting Rim Village Visitor Center and Crater Lake Lodge.

Day 7 Oregon Road Trip Itinerary: Driving to Oregon Coast and Exploring Oregon Coast

From this day, we start the Oregon coast road trip itinerary. The coast of Oregon is very varied. Rocky, sandy, covered with dense forests, often shrouded in fog. Look carefully and you will see seals or sea lions basking on the rocks. Moreover, you can encounter coyotes, roe deer, and deer on the slopes of rocks and in coastal forests. As well as gulls, hawks and other birds.

Oregon Coast: sea lions basking on the rocks.

Drive to Oregon Coast

Start driving early in the morning. You have almost a 4 1/2 hours drive to the Oregon coast.

Stop at the Girardet Vineyards

If you have more time and are a wine lover, you can change the route a bit and make a short stop on the way to the coast. You can stop at Tenmile in Girardet Winery and Wine Cellar . The place is unique. You will not only taste and buy excellent wines here, but you will also meet wonderful people who create this winery with a passion.

Moreover, if you have more time for your Oregon Road Trip, consider staying in their fabulous Chardonnay Chalet at the Vineyard . The address of Girardet Winery is 895 Reston Road, Roseburg, OR 97471. From Crater Lake, drive via OR-62 W to get there. It’s 119 miles and 2 hours 30 minutes driving. They are open Wednesday-Sunday from 11 a.m. – 5 p.m., year-round. Moreover, they are RV friendly and Family & Pet Friendly.

Agnes Stabinska, the author, is with the owners of the girardet vineyards in Oregon.

Stop at the Cape Blanco Lighthouse

Cape Blanco Lighthouse is the first fabulous stop at the coast in this Oregon Road Trip itinerary. To get there directly from the Crater Lake NP, take OR-42 E and OR-138 E. It’s 205 miles and 4 hours 20 minutes driving. If you are going from Girardet Winery, take OR-42 W and US-101 S. It’s 90 miles and 2 hours of driving.

Drive to Cape Arago Lighthouse and lodging

The next stop is at Cape Arago Lighthouse. It’s 53 miles and a 1 hour 15 minutes drive from Cape Blanco. Take the US – 101 N. Cape Arago is stunning to get there. Therefore, we suggest accommodation in this area. So, Book 1 night here.

If you are traveling by RV, book an advance spot in Sunset Bay State Park .

sunset over Oregon coast.

Exploring Cape Arago

We like this place because, in a small area, you have as many as three great state parks offering stunning views of the Oregon Coast.

  • Cape Arago State Park
  • Shore Acres State Park
  • Sunset Bay State Park

So, start this afternoon and evening by visiting each of these parks and taking at least a short walk along the coast. Wait for the sunset.

sunset from state park in oregon.

Day 8 Oregon Road Trip Itinerary: Oregon Coast Rod Trip – exploring Oregon Coast

It’s another intense day exploring the Oregon coast and a lot of driving. Therefore, start your day early. Pack some snacks for the road.

Drive and stop at Umpqua River Lighthouse

The next interesting stop we suggest doing in our Oregon road trip itinerary is Umpqua River Lighthouse. It’s 45 minutes (32 miles) from Cape Arago via Cape Arago Hwy and US-101 N.

Stop at Heceta Head Lighthouse Scenic Viewpoints

From Umpqua River, take US-101 N and drive about 40 miles (55 minutes) to the next scenic viewpoint: Heceta Head Lighthouse.

Stop at Rockaway Beach

Next stop during this Oregon Coast road trip plan at Rockaway Beach. It’s 122 miles and about 2 hours and 45 minutes driving via Oregon Coast Hwy.

wildlife oregon

Sunset at Cannon Beach and lodging

Rockaway Beach is just a 40-minute drive and 26 miles from Oregon’s famous Cannon Beach. Try to get there at sunset.

We suggest booking 1 night in this beautiful area. If you are looking for something special, you can choose one of the exclusive beachfront hotels as Surfsand Resort or Hallmark Resort .

If you’re traveling in a motorhome, a great place to spend the night is Cannon Beach RV Resort . Book it in advance. A great choice is also Seaside RV Resort .

oregon wildlife

Day 9 Oregon Road Trip Itinerary: Exploring Oregon Coast and returning to Portland

This is the penultimate day of our Oregon Road Trip Itinerary. We suggest you focus on the rest of the Oregon coast. You can stay in Cannon Beach and relax on the beach. Except for Cannon Beach is worth visiting Ecola State Park and taking Clatsop Loop Trail to see Tillamook Rock Lighthouse.

Or you can continue to go north. You can drive to Lewis and Clark National Historical Park and Astoria (it’s about 40 minutes from Cannon Beach). If you decide to go through Astoria, visit Astoria Pier and Marina, Cathedral Tree Trail, and Astoria-Megler Bridge.

Moreover, you can check Goonies’ film locations. And then, from Astoria, drive via US-30 E and I-5 S and return to Portland. It’s 105 miles and 2 hours of driving.

If you have more time, you can go shopping in Portland. Remember that there is no sales tax in the state of Oregon, so it’s worth shopping here. It is much cheaper. For more things to do, you can check in our detailed 3 days in Portland Itinerary .

oregon sunset

Day 10 Oregon Road Trip Itinerary: Exploring Portland and Columbia River Gorge/Multnomah Falls

cascad of water from Multnomah Falls.

We don’t know how much time you have on the last day of your Oregon road trip, so modify it according to your needs. If you do not have too much time on day 10, transfer your visit to Multnomah Falls and Columbia River George to day 9 or 1 of the Oregon Road Trip Itinerary.

Multnomah Falls is an icon of the Pacific Northwest. So, it’s worth your visit. It’s only 40 minute drive from Portland. More photos, tips, and directions we described in a separate article about Multnomah Falls and Columbia River Gorge .

How to shorten this Oregon Road Trip Itinerary to 7 days?

If you only have 7 days for your Oregon road trip and you would like to see all the places we write about, we suggest the following solution. Book 1 instead of 2 nights in Sisters / Bend. Remove Tamolitch Blue Pool Hike from the plan. Book 1 instead of 2 nights at Crater Lake NP. Make only a scenic drive loop and stop at the park’s best viewpoints. Finally, shorten your stay on the Oregon coast.

How to extend this Oregon Road Trip Itinerary to 14 days?

If you have 14 days for your Oregon Road Trip, you can, of course, spend more time in each place we describe. Depending on your preferences, you can spend more time in the mountains or at the seaside.

Add to your Oregon Road Trip Itinerary Alvord Desert and Hot Springs

But you can also visit other interesting places . One of our favorites we suggest adding to your Oregon road trip itinerary is Alvord Desert with Alvord Desert Hot Springs and Crystal Crane Hot Springs .

If you want to see the desert and desert hot springs, adding them to your Oregon road trip itinerary is best after visiting Sisters and Bend. So, take US-20 E and OR-78 E to get there. It’s about 260 miles and 4,5 hours of driving.

Agnes Stabinska, the author, on the road to Alvord Desert.

Add to your Oregon Road Trip Itinerary Covered Bridges of Oregon

Another option is adding some covered bridges to your Oregon road trip itinerary. We have described the most beautiful Oregon-covered bridges . It’s best to add them to your Oregon Road Trip Itinerary on your way to Crater Lake NP. Detailed GPS coordinates you will in our post.

We hope this article helped you plan your Oregon Road Trip. If you like our Oregon Road Trip Itinerary, please share it! We wish you a fabulous Oregon adventure!

covered bridges in Oregoon.

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Agnes Stabinska is a writer, photographer, and co-founder of The Van Escape. She loves wildlife, landscape photography, and outdoor adventures, especially hiking, camping, and exploring U.S. national parks. Although she has traveled to many countries for almost 20 years, her favorite places are Alaska, the American Southwest, and the Pacific Northwest, which she often visits and explore with her partner, Chris. Their travel tips, itineraries, and recommendations will help you get away from it all and plan a wonderful vacation.


The only place I have done in the Pacific North West is Cape Flattery and Seattle and as an outdoor person, I got a lot to do in Washington, Montana and also Oregon. I have always dreamt of going to Oregon and try and hit up as much as I can including the Pacific Crest trail. You have giving me more ideas on your list here including those waterfalls! I might wait until my daughters have got a bit older so we can do outdoorsy stuff together. (living in the UK sucks sometimes when all the amazing nature stuff in the US is on the west coast!) 😛 

Well I guess I would have been $500 without reading this article. I’m not used to states where they fill up your gas tank for you! Ten days still doesn’t seem like long enough to see all of these sites. My gosh, the state is so beautiful especially Multnomah Falls, Crater Lake and the Hot Springs. I just want to see it all! Maybe I should move, lol.

You sure take some really good photographs. The waterfall  has given me new goals. And I would love to see Shaniko. In India, we don’t fill our own fuel, so that part is easy to handle. But the drive looks super in Oregon. 

So glad I came across this Oregon road trip itinerary! I am planning a road trip from Minnesota to the west coast for this upcoming summer and didn’t know where I should go…. Now I know, Oregon! I have been to Seattle and many spots in California, but haven’t been to any of these beautiful spots in Oregon.

I would like to visit Oregon, especially the coast and the hot springs. As of now, I prefer to stay away from Portland area. I think I read about Sister from your post before. Interesting town. So, by cross out Portland from the itinerary, 7 days will be enough for us.  

I have been wanting to visit Oregon for a while so this is a great comprehensive list of things you must see. I love all the nature and scenic views, so I’m sure a road trip is a great way to embrace that! Thank you for all the information!

I haven’t been able to do too many road trips till now except few when in Europe. This Oregon road trip certainly looks one I must do. Thanks for all the comprehensive information which would certainly help when we plan a trip there. Seeing the bridges of Oregon would be exciting too.

PNW has long been in my bucketlist! I can imagine doing it on a roadtrip with a campervan. The trails, nature and mountains that can be witnessed seem so amazing. I love your waterfall additions. This road trip will def be on our dream destinations one day.

Wow that’s interesting that in Oregon there are people to fill the fuel and doing on our own attracts a fine. Coming from India this is common but in Australia we have to do it on our own. Anyway I have never been to Oregon and this road trip definitely seems epic and the pictures look awesome. I will keep this itinerary in mind when I plan a trip in future.

Wow, what a great comprehensive guide to visiting Oregon! I’ve always wanted to visit Crater Lake and now I have even more places to add to my list. There really is something special about the Pacific Northwest, it’s such a gorgeous area.

Ooh saving this. What a fab looking itinerary. I have travelled extensively around the US but not been around Portland and Oregon yet. Keep hearing good things. May have to wait a while before returning to the States, but this trip will be high on my list!

What a great Oregon road trip itinerary! Yes, I would add more time at the vineyards, but that’s just me! I would also love to just sit out and watch the seal & sea lions! I think I would also really enjoy visiting the Crane Hot Springs Resort! 

Truly Oregon is such a pretty state. We’ve done all those you mentioned here. Perhaps more days for Bend, Painted Hills, and caves of Oregon!

Love the ghost town you mentioned and the wineries you included! so cool!

This was one very detailed itinerary for a road trip in Oregon. I don’t think I’ve seen anything that comes close to offering this level of information for a holiday idea. The photos you used are amazing as well. If I live in the US, I would definitely try this road trip out

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How to Plan the Perfect Weekend Road Trip Through Oregon

While unpaved roads and covered wagons are (thankfully) a thing of Oregon Trail past, you’ll still find bucolic wineries, charming stays, and impressive scenery worth the drive. Here’s how to see it all in a weekend.

An avid Italophile, Laura is always on the hunt for the next great travel trends, luxury hotels, best places to eat and drink, and hidden gems. Her writing has appeared in dozens of publications. She also co-wrote "New York: Hidden Bars and Restaurants," an award-winning guide to the city's speakeasy scene.

See recent posts by Laura Itzkowitz

Day 1: Portland

MORNING Start your trip in Portland, one of the Pacific Northwest’s most dynamic destinations known for its enterprising chefs, local artists, surplus of microbreweries and coffee shops, and laid-back sensibility that extends to its best hotels. The Ace is an obvious choice, though the vibe is more college dorm than chic hotel. For something a bit more grown-up but still fun, stay at the Sentinel . The grand lobby retains details from the building’s historic past, while rooms are done up in tweed and evergreen.

Explore More: See hotel details | See all Portland, OR hotels

AFTERNOON After you check in, head to Pine Street Market for lunch—it’s a collection of stalls by up-and-coming chefs and producers as well as some of Portland’s most beloved restaurants. We loved the green falafel pita at Shalom Y’all and salted caramel soft serve at Salt & Straw’s Whiz Bang Bar . Walk or bike your lunch off along the Willamette River, then head a few blocks west to check out the famous Powell’s Books (JS Tip: A tote bag from Powell’s makes a great souvenir) and quirky boutiques like Tender Loving Empire and Woonwinkel . Or visit the International Rose Test Garden , where you might feel like Alice in Wonderland frolicking around the hedges blooming with brilliantly colored and striped roses. The nearby Japanese Garden is worth a stop if you have time.

EVENING For happy hour, book a table at the Multnomah Whiskey Library , a speakeasy that looks like an old-school library except whiskey bottles line the shelves instead of books. The bartenders serve more than their fair share of Old Fashioneds, but if you ask them for a recommendation (and you should), they’ll geek out over obscure whiskey cocktail recipes. While “farm-to-table” may be a buzzword, Portland chefs take it very seriously, and there are so many standout restaurants here that you really can’t go wrong. One of our favorites is  Pok Pok , which truly lives up to the hype with its multi-flavor, Chaing Mai-style dishes and famous chicken wings. If you’re in the mood for a nightcap, head to Pépé Le Moko , the Ace Hotel’s barrel-vaulted underground cocktail lounge for an espresso Martini made with Stumptown coffee.

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Photos by Chris Hornbecker

Day 2: The Columbia Gorge and Willamette Valley

MORNING Fuel up in the early hours with Stumptown coffee and a donut. Skip the long lines at Voodoo and head straight to Blue Star Donuts , which makes creative flavors like blueberry bourbon and PB&J. Portlanders love having nature so easily accessible from the city, so do as the locals do and take a detour to see the majestic Columbia Gorge and Multnomah Falls, about 30 minutes east of Portland. A drive along the winding Columbia River Highway takes you passed several other waterfalls, some of which you can hike right up to.

AFTERNOON When you’re ready to vineyard-hop, drive 90 minutes to Carlton, your first stop in the Willamette Valley. Figuring out where to start among the region’s 500 individual wineries can be a bit daunting, but a few stand out from the pack—including Sokol Blosser . Founders Bill Blosser and Susan Sokol Blosser planted their first vines in 1971, and they’re still leaders when it comes to sustainability and organic farming. Stop by to taste their excellent Pinot Noirs and Rieslings in the modern tasting room that looks out over the surrounding valleys. After the wine tasting, you’ll need to fill your stomach. We recommend lunch at The Horse Radish, a casual café that serves great salads and sandwiches on freshly baked bread.

RELATED: 7 Gorgeous Wine Country Hotels Around the World

When you’re ready for another round, head to the Stoller Family Estate in nearby Dundee Hills. Many wineries buy grapes from other vineyards, but not Stoller. In addition to Pinot Noir, they produce Pinot Gris, Chardonnay, Riesling, and Syrah using grapes grown on their 373 acres of vineyards. Fun fact: the airy, modern tasting room runs on solar panels and features reclaimed wood from Powell’s bookstore. If you can, snag one of the Adirondack chairs on the patio for sips with a view.

EVENING Check into the award-winning Allison Inn & Spa , the Willamette Valley’s most luxurious hotel. Of course, this is Oregon, so the property isn’t just beautiful; it’s also LEED Gold-certified. Drop off your bags in one of the 85 spacious rooms and unwind with a walk around the sculpture-dotted gardens or a dip in the pool before dinner at the hotel’s restaurant Jory, where chef Sunny Jin (an alum of the French Laundry and El Bulli) whips up mouthwatering seafood and veggies grown in the property’s garden.

Explore More: See hotel details | See all Newberg, OR hotels

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Stoller Vineyard by Mike Haverkate

Day 3: The Pacific Coast

MORNING If you haven’t fully explored the Allison yet, you’ll want to spend some time there this morning—perhaps to indulge in a treatment at the renowned spa, work out in the fitness studio, or request a tour of the chef’s garden, which is dotted with rows of hazelnut trees (Oregon is the country’s largest producer of hazelnuts).

AFTERNOON Stop for a quick bite at Red Hills Market in Dundee before hitting the road. You’ll drive about two hours northwest through the Tillamook State Forest before reaching Cannon Beach on the Pacific Coast. The beach is known for its giant Haystack Rock and the quaint shingled houses lining the shore. Don’t expect to swim, though: even in summer, it can be cold, so bring a warm jacket.

RELATED: The Dreamiest Beaches to Hit Up in Fall

EVENING There aren’t a lot of hotels in town, but if you want to stay overnight, the Waves is a good option. What the place lacks in style it makes up for in location—right on the oceanfront just minutes from Cannon Beach village with easy beach access. Otherwise, make your way back to Portland on the US26 for one last night in this wild, wonderful state.

Explore More: See all Cannon Beach, OR hotels

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North America , Oregon , Western US & Canada · December 6, 2023

The Perfect 5-Day Oregon Itinerary

Oregon has so much to offer with stunning waterfalls, rugged coastlines, farm-fresh produce, forest hikes, city life, and much more. This 5-day Oregon itinerary will help you discover the best things to do in Oregon to make the most of your trip!

* Disclaimer: This post contains affiliate links. If you make a purchase through the link then we will receive a small commission at no extra cost to you. We really appreciate your support!

The Best Things to Do in Oregon in 5 Days

Best Things to Do in Oregon | 5-day Oregon itinerary | Simply Wander

Table of Contents

Arrive in portland, drive to mount hood, check into your airbnb, dinner at chicali cantina, breakfast at dragonfly cafe, drive the “waterfall highway” in the columbia river gorge, discover farm-fresh food on the hood river fruit loop drive, enjoy the views at trillium lake, dinner at mount hood village, explore portland, drive to oceanside, dinner at roseanna’s cafe, morning walk on the beach, ride e-bikes on the beach in pacific city, dinner and s’mores on the beach, visit tillamook creamery, take a ride on the oregon coast scenic railroad, drive to cannon beach.

Today will be a travel day, whether you are flying or driving into Oregon.

If you are flying, you’ll want to fly into Portland and pick up a rental car. I would recommend checking RentCars or Expedia for the best rates on rental cars.

After getting a rental car, you’ll want to drive about 50 minutes east of the city and enjoy the beauty of Mount Hood, one of Oregon’s most scenic destinations.

I would highly recommend booking a cozy cabin near Mount Hood for a few nights.

We booked this cabin in Brightwood on Airbnb and especially loved soaking in the hot tub overlooking the river.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

It was a great location close to restaurants and shops, but felt private and secluded.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

After dropping your luggage off, head to dinner at Chicali Cantina in Mount Hood Village.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

Enjoy fresh homemade guacamole and salsa and a big fat burrito on their outdoor patio.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

End the evening soaking under the stars in the hot tub while listening to the babbling sounds of the creek below.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

It’s the best way to end a long travel day!

Start your day with a hearty home-cooked meal at the nearby Dragonfly Cafe.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

Our favorites are the giant cinnamon roll, the biscuits & gravy, the steel-cut oatmeal, the french toast, and the most delicious hashbrowns.

The Columbia River Highway is the first scenic highway in the US to be designated as a National Historic Landmark.

It crosses through some of the most scenic landscapes in Oregon and is home to countless waterfalls.

Latourell Falls is the first waterfall you’ll come to and I would recommend taking the short 0.2-mile trail to the base of the falls.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

There is a longer 2.1-mile loop trail that goes up above the waterfall if you have time.

You’ll also want to stop at Bridal Veil Falls a little further up the road. Here you will find a 0.6-mile out-and-back trail leading to the base of a two-tier 120-foot waterfall.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

There is also the option to take a 0.4-mile loop trail to a scenic overlook of the Columbia River Gorge.

You definitely won’t want to miss Multnomah Falls, visiting it is one of the best things to do in Oregon.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

This 620-foot-tall waterfall is the tallest in Oregon and is the crowning jewel of the Columbia River Gorge.

Just keep in mind that timed reservations are required from the end of May until the beginning of September.

There are plenty of other waterfalls to visit in the gorge, but those are a few that you won’t want to miss!

The “Fruit Loop” is a 35-mile scenic drive in the Hood River Valley that can be accessed from the Columbia River Highway.

It will take you past farm-to-table restaurants, roadside fruit stands, wineries, orchards, and flower fields.

I would recommend stopping for lunch at The Gorge White House.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

Order their flatbread pizza or burgers that are made with ingredients grown right at the farm.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

You can also pick fresh produce or flowers in their U-pick orchards and fields.

The Hood River Lavender Farm is a great place to stop for lavender-infused products and to take photos in the summer when the lavender is in full bloom.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

Packer Orchards & Bakery is our favorite spot to pick up fresh fruit and homemade goodies like pies, cinnamon rolls, jams, cookies, and so much more!

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

As you make your way back to the Airbnb, you’ll pass by Trillium Lake.

Take the short detour through Trillium Lake Campground until you reach the Trillium Lake Dam parking lot.

Here, you will be able to see Mount Hood perfectly reflected in the water.

Best Things to Do in Oregon | 5-day Oregon itinerary | Mount Hood #simplywander

The best time to visit is early in the morning or later in the evening to capture the mirrored reflection .

In the summer, paddle board rentals are available on the beach near the dam.

There are several different dining options in Mount Hood.

I would recommend Koya Kitchen for Asian-fusion dishes served in a cozy ambiance, Brightwood Tavern for hearty burgers and pizza, Skyway Bar & Grill for smoked meats and barbecue, or Al Forno Ferruza for authentic Italian dishes.

For more details and recommendations in the area, see our guide 10 Things to do in Mount Hood, Oregon.

For this 5-day Oregon itinerary, I would highly recommend spending a few days in the mountains and a few days on the coast to take advantage of all that Oregon has to offer.

While driving from Mount Hood to the coast, stop and spend a few hours in Portland exploring the city.

Mississippi Avenue is a great walkable neighborhood with trendy shops and restaurants.

Best Things to Do in Oregon | 5-day Oregon itinerary | Portland #simplywander

Stop for brunch at Gravy and order their buttermilk biscuits that are swimming in a savory sausage gravy.

Best Things to Do in Oregon | 5-day Oregon itinerary | Portland #simplywander

The creme brulee oatmeal is almost too pretty to eat, but tastes as good as it looks!

Best Things to Do in Oregon | 5-day Oregon itinerary | Portland #simplywander

Powell’s Books is also worth a stop.

Best Things to Do in Oregon | 5-day Oregon itinerary | Portland #simplywander

It is the world’s largest new & used bookstore, there’s no place quite like it!

Best Things to Do in Oregon | 5-day Oregon itinerary | Portland #simplywander

23rd Avenue has some fun boutique shops, and be sure to stop at Salt & Straw for a scoop of their delicious hand-crafted ice cream.

Best Things to Do in Oregon | 5-day Oregon itinerary | Portland #simplywander

There are plenty of great places to stay along Oregon’s Coast, but we love Oceanside. It is a bit of a hidden gem away from the crowds.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

We stayed in this beach cottage overlooking the ocean and loved it.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

A few other options for accommodations include  The Oceanside Inn , the  Coastal Comfort , and the  Blue Moon  vacation home.

Oceanside is a small community with several restaurants and cafes within walking distance from the beach.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

Roseanna’s Cafe is a great option for fresh seafood and spectacular ocean views at sunset.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

Mornings on the coast of Oregon are often moody with heavy mist-shrouded skies and a thick fog rolling off the ocean.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

I would recommend fully embracing the quintessential Oregon weather by taking a morning walk on the beach.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

The Oceanside Beach Trail is a 0.86-mile out-and-back trail that leads along the scenic coast. This is a great beach for shelling and rockhounding, so keep your eyes peeled for sand dollars and agates.

Pacific City is one of the few places in Oregon where you can legally drive a motorized vehicle on the beach.

The miles of scenic coastline also make it one of the best places to ride an e-bike right on the beach.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

Fat tire e-bike rentals are located in town and there are several different rides that you can do.

We loved the 10-mile roundtrip ride along Bob Straud Beach to the end of the spit, it was one of our favorite things to do in Oregon!

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

McPhillips Beach is also a great place to ride and take in the stunning formations at Cape Kiwanda.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

There are also several bike paths through town where you can stop and grab a bite to eat at Grateful Bread Bakery, or a sweet treat at Pacific Coast Candy Shop.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

On the way back to your vacation rental, stop at a grocery store and pick up some ingredients for dinner and s’mores.

We stopped at Safeway in Tillamook and got ingredients for soup, salad, and garlic bread. After going and doing so much, it’s nice having a relaxing evening staying in.

You’ll also want to pick up a fire starter log and ingredients for s’mores.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

Oceanside is one of the few beaches in Oregon that allows beach fires and you’ll find several designated fire pits in the sand.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

As long as there are no fire restrictions in place, it’s such a memorable experience to roast s’mores at sunset with the ocean waves crashing in the background.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

It truly was one of our favorite things to do in Oregon.

Tillamook Cheese has a reputation for being some of the best cheese on the market!

The Tillamook Creamery is located about 20 minutes from Oceanside in the small farming community of Tillamook, Oregon.

Visitors can stop in and take a free self-guided tour to witness first-hand how the cheese is made.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

You can also sample fresh cheese, pick up some “cheesy” souvenirs, and try deep-fried cheese curds and housemade ice cream from the cafe.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

The Oregon Coast Scenic Railroad hosts a variety of scenic coastal train rides throughout the year.

In the fall, they offer leaf-peeping train rides, and there are themed holiday train rides in the winter.

During the warmer months, the scenic 30-minute train ride from Garibaldi to Rockaway Beach is a popular option.

Best Things to Do in Oregon | 5-day Oregon itinerary | Oceanside #simplywander

Once you reach Rockaway Beach, you can get out and explore the cute oceanfront town before heading back to Garibaldi. Tickets are reasonably priced and it’s a fun afternoon activity!

Cannon Beach is one of the most iconic spots in all of Oregon. It is the backdrop for many blockbuster films, including the 1980s classic, The Goonies .

Best Things to Do in Oregon | 5-day Oregon itinerary | Cannon Beach #simplywander

Cannon Beach has also earned the title of “One of the World’s Most Beautiful Places”, according to National Geographic.

It is worth making the one-hour drive from Oceanside to Cannon Beach to see the famous 235-foot Haystack Rock that Cannon Beach is famous for.

While you are there, check out the tidepools at the base of Haystack Rock, enjoy a meal with a view at Wayfarer Restaurant, and pick up some souvenirs along North Hemlock Street.

Best Things to Do in Oregon | 5-day Oregon itinerary | Cannon Beach #simplywander

For more details and recommendations in the area, see our guide 7 Things to Do in Oceanside, Oregon .

After you’re done visiting Cannon Beach, it’s time to head back and pack up for your trip home.

It’s always sad to see a trip come to an end, but hopefully this itinerary will help you discover the best things to do in Oregon so that you can make the most of your time there!

If you’re looking for more girls’ trip inspiration, see our guide 11 Best Girls’ Trip Destinations in the US !

*Click the button to download and print this guide to take with you on your trip!

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Coquille River Lighthouse on Bullards Beach

2. How Much Time Do You Need For Your Visit To Oregon?

If you’re like most travelers and only have a week or so to explore – don’t worry! A week is plenty of time to get a taste of what Oregon has to offer. If you’re able to stretch it to ten days, that’s even better! The more time you set aside, the more time to experience the best places in Oregon.

My recent trip lasted ten days and I had more than enough time to do everything I wanted to do and then some.

The best time to visit Oregon depends on what you’re looking to see and do. Early spring will give you fewer tourists and a chance to enjoy many of the stops along the coast by yourself. Hotel prices will be cheaper as well.

I’d spend at least two or three days along Oregon’s coast; a couple of days exploring some inland areas; and then the rest of your time in the Columbia River Gorge.

If you’re flying into Portland and renting a car – you’ll probably do the Columbia River Gorge area first, some inland exploring, and finish on the coast before driving back to the airport.

3. Visiting Oregon’s Coast

Much like the Pacific Coast Highway in Northern California, Oregon’s coastline doesn’t disappoint. Whether it’s raining or sunny, the massive rock formations scattered about the ocean are mesmerizing as gigantic waves crash into them again and again. You’ll find plenty of places to pull over for a closer look or to hike down to beaches. Initially I thought I would be at a disadvantage traveling north. Turns out that it really didn’t matter much at all.

One tip – stop into the state’s visitor center as you arrive in Oregon and pick up a “points of interest” checklist. You’ll have an easy one page guide to the best places in Oregon along every mile marker on Highway 101. I used this thing extensively! If this is your first time visiting Oregon – this will be a life saver!

You don’t need to drive the entire Oregon coast if you’re short on time. Let’s be honest – the rocks and beaches all pretty much start to look the same after a few days. If time is not an issue, certainly knock yourself out and see it all!

best time to visit oregon

I stopped in the towns of Gold Beach; Florence; and Coos Bay. Florence had a really cool downtown area with great local restaurants.

A Few Lodging Options:

– Wildflower Inn (Gold Beach) – Awesome spot with modern, spacious rooms.

– Mills Casino Hotel (Coos Bay) – A casino with basic hotel rooms and some dining options inside.

– Driftwood Shores Resort (Florence) – Spacious rooms with views of the ocean. The staff was super friendly and helpful.

Oregon Dune Buggy Rides

One of my favorite adventure activities along the coast was a dune buggy ride in the Oregon Dunes National Recreational Area. Sand Dunes Frontier in Florence offers a wild, thrilling ride through the dunes! (Be sure to watch my Oregon Road Trip mini-doc to see the dune buggy in action!) It’s easily located off Highway 101.

how to travel to oregon

4. A Few Hot Tips For Your First Visit To Oregon

Things to bring / have on hand.

  • Have brand new windshield wipers. I lucked out and only had a few days of rain during my visit. Odds are your luck won’t be as great. (But I hope it is!) My wipers were shot and I didn’t realize until I couldn’t see well on wet, foggy backroads and that’s not good.
  • Bring good hiking shoes with excellent tread. If you want to really explore the coastal beaches, many of them are covered in rocks which can be slippery. Most of the trails I found to be in excellent condition – but don’t do this trip in basic tennis shoes. I basically kept my hiking shoes on the entire time I was on the coast.
  • Don’t assume that because it’s spring or summer that it’s going to be warm. The weather can change in a heartbeat. Pack sweatshirts or hoodies!

Pumping Gas

It’s weird – but Oregon (in some places) requires an attendant to pump your gas for you. They passed a law recently that changes the requirement a bit but some counties can still enforce it. Just warning you so you aren’t stunned when a stranger approaches your car and asks for your credit card at the gas pump!

first visit to oregon

5. Be Sure To Visit Some Of Oregon’s Small Towns

In my quest to visit every state capitol, I had to make a pit stop in Salem. Just my luck – it was under construction. Oregon has a lot of really cool small towns and medium size cities that are worth visiting. Eugene is a fun college town and nearby is Springfield – the real hometown of “The Simpsons”! (Creator Matt Groening grew up in nearby Portland.) Bannon is a cool spot along the coast with lots of shops and places to dine. It’s not far from a couple of awesome lighthouses.

Silverton was another great small town! It’s close to South Falls – which was one of my favorite waterfall hikes. (Easy hike but the waterfall is beautiful.) It’s also home to the Oregon Gardens – a large botanical garden and resort.

how to travel to oregon

In the Columbia River Gorge area there are several neat towns to explore or use as your home base. Cascade Locks is a great spot to stay if you’re interested in waterfall hikes or biking along the river. About 20 miles to the east is the town of Hood River which has a wonderful downtown area and fun vibe to it.

I stayed at the historic Hood River Hotel which had awesome spacious rooms – almost like an apartment. This was a great base to go explore the nearby Mount Hood National Forest. There’s a toll bridge downtown that will take you directly across to the Washington side of the river as well.

how to travel to oregon

6. Don’t Miss The Columbia River Gorge Scenic Area

I have an entire post on visiting the Columbia River Gorge but the nitty gritty is this: do NOT miss this part of Oregon. It’s one of the most beautiful places in the entire country and definitely among the best places to see in Oregon. In fact, if you had to choose just one place to explore in the state – this would be it. There are countless waterfalls to view along the road and even more that can be found with a beautiful nature hike in the forest.

One of the most photographed waterfalls in the world is located here. Multnomah Falls is easy to find and requires no hiking. However, it is incredibly busy during peak tourism months. The best time to visit Oregon and sites like these is early spring or late fall when there are fewer people. You’ll want to check ahead to see if reservations are required or at least plan an early visit to beat some of the crowds.

first visit to oregon

Hopefully you’ve found at least some inspiration to plan your own Oregon road trip! If you’re looking for other recreational ideas or lodging information – you can visit Oregon’s official state tourism website – Travel Oregon .

My thanks to the Oregon State Tourism Office for helping me plan this road trip and going above and beyond to make sure it all went smoothly!

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Dang Travelers


The Perfect Oregon Road Trip Itinerary: Must See Stops and Things to Do

Oregon is a picture-perfect coastal state in the Pacific Northwest known for its astounding views, outdoor lifestyle, and wild natural beauty. It is home to one of the largest river gorges and to the deepest lake in the United States. Discover the best it has to offer with this ultimate two week Oregon road trip itinerary.

Oregon Road Trip Summary

How many days does it take to road trip Oregon? You can spend months exploring the country’s ninth-largest state, but if you don’t have that kind of time, you can cut it down anywhere from a 5 day Oregon road trip to two weeks. 

Ideally, you should plan at least a week to two weeks to truly appreciate its beauty.

Plan your road trip along this loop starting and ending in Portland, it will take you to many of the highlights.

  • Astoria, 1 night
  • Cannon Beach, 1 night
  • Newport,1 night
  • Florence, 1 night 
  • Brookings, 1 night 
  • Crater Lake National Park, 3 nights
  • Bend, 2 nights
  • The Dalles, 2 nights
  • Portland, 2 nights

Oregon Road Trip Map

how to travel to oregon

Best Time of Year 

The best time of year to plan an Oregon road trip depends on the activities you are interested in and your budget. 

Summer is the most popular season, from wine tasting to biking in pleasant temps. But, it comes with occupied rooms and a hefty price tag. No road-tripping on the fly during peak season.

Fall is met with sunny skies, crisp air, and an array of orange, yellow, and red leaves. Even though you can expect a few sprinkles, it’s a popular time for hiking, pumpkin patches, and festivals. 

The rainy and winter season between October and May triggers lower hotel costs and fewer tourists with moderate temperatures. Winter activities include skiing, tubing, sledding, hot springs, and snowmobiling. Just make sure to pack layers!

Then spring arrives with new growth and invigorating temps; it’s a good time to see wildlife and the many waterfalls throughout the state. 

When it comes to outdoor adventure, Oregon has something to offer in any month.

HOT TIP: If you want to spot migrating gray whales on the coast, plan your visit from March through May or mid-December through mid-January.

how to travel to oregon

Car Rental Tip – How to Avoid High Prices

Car rentals in Oregon – on the entire West Coast actually – are significantly higher than those in other areas of the country. When we first started researching prices, the search engines came up with $80 – $85 per day!

A tip we learned is to book offsite away from the airport and take public transportation or a Lyft to the rental company. 

Ultimately, we ended up with a Budget Rent a Car fifteen minutes from the airport and paid $29 per day with taxes and fees during peak season.


The Astoria Riverwalk is just one of the must-see things on your two week Oregon road trip!

*Disclaimer: This post contains affiliate links, if you book through our link we will receive a small commission at no additional cost to you. Thanks for supporting the blog!*

Day 1: Astoria

Once you pick up your rental car, kick off this ultimate Oregon road trip in Astoria, the oldest settlement west of the Rockies. Sitting on the banks of the Columbia River and only a few miles away from the Pacific Ocean, the small city is more like a historic fishing village with a Victorian flair.

If you’ve ever seen the 80’s coming-of-age film, The Goonies , then Astoria might look a little familiar to you. Hop on a pilgrimage around town and try to find all the locations. 

What to See & Do: Goonies Film Locations, Astoria Pier and Marina, Astoria Column, Cathedral Tree Trail, and Astoria-Megler Bridge.

Where to Eat & Drink: Coffee Girl, Buoy Beer Company, Bowpicker Fish & Chips, or Fort George Brewery.

Where to Stay: Waterfront Hotel with Indoor Pool & Free Breakfast, walking distance to all attractions

These starfish are just some of the marine wildlife we spotted on Oregon's coast.

Day 2: Cannon Beach

It’s time to hop on Highway 101, the 347-mile scenic road to discover Oregon’s beautiful and wild coastline. Cannon Beach is a short drive from Astoria so you can technically pick one or the other destination if you need to shorten your trip, but I think it deserves an overnight.

Once listed as “one of the world’s 100 most beautiful places” by National Geographic, Cannon Beach has a lot to see and do including exploring the quaint town itself.

On the Way: Fort Stevens State Park, Wreck of the Peter Iredale, Lewis and Clark National Historic Park, walk the Seaside promenade, and eat at Bell Buoy of Seaside.

What to See & Do: Ecola State Park, Cannon Beach, Clatsop Loop Trail to see Tillamook Rock Lighthouse (bring binoculars), and Haystack Rock. 

Where to Eat & Drink:  Public Coast Brewing Company, Lazy Susan Cafe, Castaways, or Pelican Brewing Company.

Where to Stay: Beachfront Lodge with Continental Breakfast or Inn with Breakfast & Garden

HOT TIP: You can see all kinds of diverse marine life on Oregon’s beaches, it’s one of the top things to do when exploring the coast. The best time to go tidepooling is one to two hours before the low tide. Check the tide times here.


If you've ever seen the movie, The Goonies, then you will recognize Haystack Rock immediately.

Day 3: Newport

There are a lot of stops along the two-and-a-half-hour drive to Newport, one of the biggest cities on the coast. From the aquarium to the glassblowing studio, there’s a lot to choose from once you get there. 

If you want to do something unique, reserve a pedal-powered quadricycle at Oregon Coast Railriders in Wheeler and go for an 11-mile jaunt through the countryside on an unused railroad track.

On the Way: Haystack Rock, Oswald West State Park, Neahkahnie Mountain Trail Viewpoint, Silver Point Interpretive Overlook, Tillamook Creamery, Cape Meares Lighthouse, Octopus Tree, Cape Lookout, Beverly Beach State Park, Cape Foulweather, Devils Punchbowl State Natural Area, and Yaquina Head Lighthouse.

What to See & Do: The Oregon Coast Aquarium, Historic Bayfront, Oregon Coast Glassworks, Hatfield Marine Science Center (it’s free with a suggested donation so you can stop in for as long as you’d like), sunset on Nye Beach, and the Farmer’s Market on Saturdays.

Where to Eat & Drink: Georgie’s Beachside Grill, Carl’s Coffee, Local Ocean Seafoods, Chowder Bowl, Rogue Ales and Spirits, or Panini Bakery.

Where to Stay: Adorable and Highly-Rated Motel with balconies and fireplaces

One of the must-see things in Newport, Oregon is Yaquina Head Lighthouse.

Day 4: Florence

Discover one of the most photographed lighthouses in the United States, go underground in a large sea cave to find grunting sea lions, and explore a quiet gem on the coast. 

Around mile marker 164 you’ll find Yachats, pronounced Yah-hots, a welcoming small village at the mouth of the Yachats River. If you have time stop in Yachats Brewing for quality beer and farm-to-table cuisine. 

You’ll spend the night situated on the banks of the Siuslaw River in the charming riverfront district of Florence. 

On the Way: South Beach State Park, Seal Rock State Recreation Site, hike the one-mile loop at Yachats Ocean Road State Park, Devil’s Churn Scenic Overlook, Cape Perpetua Lookout,  Thor’s Well, and Neptune State Scenic Viewpoint.

What to See & Do: Eat on the river, Take a Dune Buggy Tour, Florence Old Town, Hobbit Trail with the China Creek Trail, Heceta Head Lighthouse, and Sea Lion Caves. 

Where to Eat & Drink: River Roasters, Homegrown, BJ’s Ice Cream Parlor, or Waterfront Depot Restaurant.

Where to Stay: Charming Motel with a Cabin-Vibe walking distance to Old Town


The top places to visit on this Oregon travel list include Crater Lake National Park, Smith Rock State Park, the Columbia River Gorge, and so much more! Here's a perfect two week itinerary that starts and ends in Portland. #pacificnorthwest #oregon

Day 5: Brookings

After leaving Florence, you’ll travel from sandy dunes to the untamed wild section of the drive. With mountains and forest on one side and the tumultuous ocean on the other, the scenery is spectacularly dramatic. 

More than likely, the road will be uncrowded with a quiet fishing port or artsy town popping up here and there. Four of the eleven lighthouses on Oregon’s waterfront line the southern stretch and it feels like every few miles you’re running into a state park. 

Stop just six miles short of the California state line for your overnight in Brookings, the southernmost city on the coast. 

On the Way: Simpson Reef Overlook, Face Rock State Viewpoint, Sunset Bay State Park, Shore Acres State Park, Cape Arago Lighthouse, Coquille River Lighthouse, Face Rock State Scenic Viewpoint, Sisters Rock State Park, Pelican Bay Lighthouse, and Cape Blanco Lighthouse.

What to See & Do: Samuel H. Boardman State Park, Azalea Park if visiting in the spring, Port of Brookings-Harbor Marina Boardwalk, Harris Beach State Park, and Chetco Point Park

Where to Eat & Drink: The Crazy Norwegians Fish and Chips, Tasty Kate’s, Khun Thai.

Where to Stay: Comfy Beachfront Hotel with Water Views

*If you wake up early enough the next morning, drive the extra 23 miles south to Redwood National and State Park for a detour if you’re like us and love to see all the national parks.”

Garden at Shore Acres State Park on Oregon's coast.

Days 6 – 8: Crater Lake National Park

Crater Lake is one of the most magical landscapes in the United States. Many people asked if our pictures were filtered and if the lake really is that blue. And I’m here to tell you yes, it really is that blue. 

Formed in the remains of an ancient volcano, at 1,943 feet deep, it is the deepest lake in the United States and one of the top ten on earth. Excellent visibility, measured at 144 feet, along with the depth and purity contributes to the brilliant blue color.

Any southern Oregon road trip should include this stop! Plan for at least three days so you can hike, take the scenic drive, and a boat tour of the lake. 

What to See & Do: Rim Village Visitor Center, Crater Lake Rim Scenic Drive, Watchman Trail, Standard Boat Lake Cruise which includes the Cleetwood Cove Trail, Garfield Peak Trail, Crater Lake Lodge, and the Discovery Point Trail. Read about our favorite hikes here at The Best Crater Lake Hiking Trails.

Where to Eat & Drink: Pack in your own lunches, Prospect Cafe, Crater Lake Lodge, and Prospect Pizza.

Where to Sta y:   Hotel & Suites near the Park or Mountain Cabin with Balcony


Any southern Oregon road trip would not be complete without a few days at Crater Lake National Park. Crater Lake is jaw-dropping beautiful.

Days 9 – 10: Bend

If looking up real estate the first day of a visit is any indication of how impressive an area is then Bend is uber awesome. You’ll only be able to scratch the surface of all this mountain town has to offer within a few days so you’ll definitely be planning another trip back.

Situated in the foothills of Oregon’s Cascade Range, the upscale community is at the core of an outdoor playground with countless activities throughout the entire year. The attractive downtown area has a wide range of hip coffee shops, local eateries, and innovative art galleries.

On the Way: Take the Cascade Lakes National Scenic Byway and pull over at a few of the lakes with lunch or drinks at Elk Lake Restaurant. 

What to See & Do: Try a local craft brewery, Todd Lake Loop Trail, Walk around Downtown, Tumalo Falls, Old Mill District, and Smith Rock State Park.

Where to Eat & Drink: The Cafe, Crux Fermentation Project, Spork, Bangers & Brews, and Wild Rose Northern Thai Eats.

Where to Stay: Welcoming Hotel with Free Breakfast, Beautiful Views in a Great Location near the Old Mill District.

Days 11 – 12: Columbia River Gorge 

Let’s adventure into America’s largest National Scenic Area, the Columbia River Gorge. Separating Washington and Oregon, this vast meandering canyon delivers breathtaking views, gorgeous waterfalls, and endless outdoor activities.

From the historic Crown Point Vista House to the horseshoe-shaped Rowena Crest viewpoint, it is a drive that you will never forget.

On the Way: Detour to Mount Hood, Oregon’s highest mountain, and hop on the Scenic Sky Chairs for a bird’s-eye view of the surrounding mountain ranges. 

What to See & Do: Elowah Falls, Bridge of the Gods, Multnomah Falls, Latourell Falls, Crown Point, Bonneville Lock and Dam, Bridal Veil Falls, Rowena Crest, Horsetail Falls, Wahkeena Falls, Hood River, and the Vista House.

Where to Eat & Drink: Thunder Island Brewing Co, The Gorge White House, Full Sail Brewing Company, Tad’s Chicken N’ Dumplins, and Columbia Gorge Hotel.

Where to Stay: Hidden Gem of a hotel with Fantastic River Views

HOT TIP: Include the 35-mile Hood River County Fruit Loop to your itinerary for a scenic drive with charming orchards, bountiful vineyards, fruit stands, and even an alpaca ranch. 

On any visit to Oregon, make sure to include Columbia River Gorge on your itinerary. Designated the largest National Scenic Area in America, the canyon is a must-see.

Days 13 – 14 Portland

The City of Roses pounds to an eclectic beat, and with its prime location in the Pacific Northwest there are a ton of things to do outdoors including gardens and parks. Read here for other Outdoorsy Day Trips from Portland. 

Bearded hipsters, emerging artists, and skilled brewmasters converge amid two mountain ranges to form Portland. With that in mind, there’s no shortage of breweries, galleries, coffee shops, donuts, or food trucks within the metropolis.

What to See & Do: Portland Japanese Garden, Washington Park, Best Rooftop Bars in Portland , International Rose Test Garden, Pioneer Courthouse Square, Powell’s City of Books, and Pittock Mansion. 

Where to Eat & Drink: Rogue Ales, Hawthorne Asylum Food Cart Pod, Radio Room, Culmination Brewing, Homegrown, Voodoo Doughnut Old Town, and Prost!

Where to Stay: Boutique Hotel with Bike Rental and Wine Reception

HOT TIP: If you don’t want to spend the money for the Japanese Garden, you can link from the MAC trail to a series of switchbacks on the Wildwood Trail for a glimpse overhead. 

How to plan the ultimate Oregon trip! Check out this 14-day itinerary of all the best things to see and do including the Portland International Rose Garden.

Have you taken an Oregon road trip? What do you recommend?

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On this awesome Oregon road trip, you'll drive the entire coast, explore Crater Lake National Coast, discover the Columbia River Gorge, and hike in one of the most beautiful state parks. #oregon #roadtrip

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Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

Latest posts from Angela

  • The Best Time to Visit the Galápagos Islands - June 26, 2024
  • Top 10 Best Things to Do in Banff National Park - June 20, 2024
  • The Best Road Trips from Chicago with Itineraries - April 15, 2024

5 Responses

Dan coleman.

I enjoyed reading about your trip all over Oregon. By any chance do you remember the exact Budget Rental car location address you picked up your car?

Dang Travelers

Hey Dan! It was the Budget at 5856 NE Columbia Blvd, Portland, OR 97218

Were the hikes you mentioned fairly easy? What about ticks, Is that something to prepare for? And last, do you think this could be done in a week? I know we wouldn’t be able to spend several nights in each place and wouldn’t be able to do or see everything but the highlights.

A week is pretty short for the entire loop, but you might be able to swing it. There are some great hikes in Crater Lake, but you could also just spend a day there (take the boat ride and see the views from the overlooks) and drive the coast.

And we had no issues with ticks at all.

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7 Day Oregon Road Trip Itinerary

How to plan an unforgettable 7 day Oregon road trip

Oregon has been on my bucket list ever since I moved to Vancouver, BC, back in 2019. Fast forward four years and I finally made it down there! On our 7 day Oregon road trip, we experienced so much – from incredible beaches and sand dunes to roaring waterfalls and the high desert. 

Oregon is such a large and diverse state which can make planning a road trip quite challenging. In this blog post, I’m sharing our exact 7 day Oregon itinerary. You’ll also find optional add-ons in case you want to extend your trip, information on entrance fees, suggestions on where to stay, and more!

Disclaimer : This blog post features some affiliate links, which means I get a small commission if you make a purchase. There’s no extra cost to you but it just helps me to keep writing these free guides and itineraries for my readers. Thank you for your support!

7 day oregon road trip: what you need to know.

There are so many wonderful things to see and do in Oregon. This 7-day Oregon itinerary is based on my own experiences but you can easily tailor this to your own travel style and add or cut any stops you see fit.

7 Day Oregon Road Trip Route Overview

Here’s a quick summary of the 7 day Oregon road trip that we did. You can do this route in either direction. We went anti-clockwise as the weather looked better at the beginning of the trip so we decided to start with the coastal section.

  • Day 1: Arrive in Cannon Beach
  • Day 2: Cannon Beach, Ecola State Park, and Cape Kiwanda
  • Day 3: John Dellenback Sand Dunes, Willamette National Forest, and Bend
  • Day 4: Bend
  • Day 5: Smith Rock State Park and Mt. Hood
  • Day 6: Columbia River Gorge (and Portland)
  • Day 7: Travel home

Below you’ll find an itinerary map for this Oregon 7 day road trip which features pins for each day’s scenic stops, hiking trails and places to eat. You can save the map by clicking on the star next to the title and use it to help gauge daily driving distances.

Before we jump in, here are some important things to know about Oregon and this road trip route:

Oregon is a big state

Oregon is a lot bigger than people realize. It’s actually the 9th largest state in the country which means you’re not going to see the entire state in one trip. Here’s a quick overview of the different regions:

  • Oregon Coast: 363 miles of beaches, rugged cliffs, sea stacks and quaint towns
  • Central Oregon: Home to the high desert and well-known spots like Bend, Sisters and Smith Rock State Park
  • Eastern Oregon: This is a vast area that deserves its own road trip and includes the Painted Hills, Pendleton and Hells Canyon
  • Mt. Hood: Mt. Hood is the highest peak in Oregon and is a popular destination for outdoor enthusiasts
  • Columbia River Gorge: This is the ‘waterfall wonderland of the Pacific Northwest’
  • Willamette Valley: The valley is home to vineyards, farmlands and orchards
  • Southern Oregon: This is a diverse region where you’ll find Crater Lake National Park, Oregon Caves National Monument and hidden hot springs

We wanted to try and see as much of the different landscapes as we could on our 7 day Oregon road trip. We spent some time on the coast before driving into central Oregon and up to Mt. Hood and the Columbia River Gorge.

This itinerary doesn’t include Eastern or Southern Oregon as it was just too far to go on a 7 day Oregon road trip. If you do have more time, I’ve included some suggestions on how to extend this road trip later in the blog post.

Where to start and end your 7 day Oregon road trip

This really depends on where you’re travelling from. We decided to drive from Vancouver so we went straight to Cannon Beach and started our road trip from there. However, if you’re flying in I recommend starting and ending your road trip in Portland. Although it’s in the northwest corner of the state, it’s actually well-positioned for this particular 7 day Oregon road trip. From Portland you can either drive west to Cannon Beach or go east to Columbia River Gorge and do this 7 day Oregon itinerary in reverse.

If you’re planning to do a longer road trip and explore Eastern Oregon as well, I would suggest flying into Portland and out of Bend. This way you don’t have to drive all the way back to Portland.

Oregon road trip itinerary

How to get to Oregon

If you live in British Columbia, Washington or Northern California, you could drive all the way or fly into Portland and rent a car. We looked into both options but it worked out much cheaper for us to hire the car from Vancouver and drive down (we saved $300).

For those coming from further away, I’d recommend flying into Portland and renting a car . I always use  Skyscanner  to find reasonable rates on flights and use  Auto Europe  for car rentals as they have great rates.

Do you need to rent a car for this 7-day Oregon road trip itinerary?

You will definitely need to hire a car for this road trip! If you’re flying into Portland International Airport you can pick up your hire car from the airport. Make sure you book in advance to get the best price.

Alternatively, you could rent a campervan instead for this 7 day Oregon road trip. Outdoorsy  is the world’s largest and most trusted RV rental market place and have a great selection of adventure vehicles. They take care of liability and collision insurance too so it’s an easy and simple way to book an RV for your trip. My advice is to work out the costs for both options and see what is cheaper. A campervan rental is usually more expensive than a car but you don’t have to pay for hotels which can be pricey. 

Cape Kiwanda in Oregon

When is the best time to do this itinerary?

With its diverse landscapes, Oregon offers unique experiences all year-round. That being said, I would recommend doing this 7 day Oregon itinerary in late spring or early autumn.

Spring is a great time to visit Oregon as the wildflowers are starting to appear and the weather is warming up. It’s also peak waterfall season as the snow has just melted so they’re incredibly powerful. There are usually fewer crowds but expect weekends to still be quite busy along the Columbia River Gorge. The downside is that higher elevation hiking trails will still be closed and there can be late snowfalls which lead to road closures. When we went, we couldn’t get down to Trillium Lake because the snow had blocked the entrance.

As with most places, this is peak tourist season so expect crowds and higher prices for accommodation. However, it’s also the best time for hiking, camping, and exploring the famous Crater Lake.

Early autumn is a nice time to visit. Although the waterfalls won’t be very powerful, the fall foliage is very pretty. The weather can be a bit unpredictable but there are fewer crowds and you can get some good deals on accommodation. I would avoid doing this road trip in late autumn as there are often snowfalls which can make travel more difficult.

Winter in Oregon is a magical time and offers great opportunities for skiing, snowboarding and snowshoeing. However, I would personally avoid doing this 7 day Oregon road trip in winter. Some areas on this route may be inaccessible due to snowfall and the mountain passes may even be closed due to winter storms. If you are planning a winter road trip, I would stick to the Oregon coast, Columbia River Gorge, and Silver Falls State Park as the roads in these areas are well-maintained.

Oregon itinerary driving conditions and tips

For the most part, the roads on this 7 day Oregon itinerary are very good. There are a few big pot holes on the road through the Willamette National Forest so watch out for them as some are quite deep. The road to Terwilliger Hot Springs is paved up until the last part where it becomes more rugged.

Some parts of the route are quite remote and you will lose cell coverage. I found that I didn’t have any service in Willamette National Forest and Mt. Hood. It also kept cutting in and out in the Columbia River Gorge. Most of the route is well signed but I recommend downloading offline maps or taking a physical one with you just in case. 

Make sure you stock up on groceries before you set off on day 3 and 5 because there aren’t many stores along the way. The same applies for gas. Fill up before you start the drive through Willamette National Forest and Mt. Hood.

Hood River in spring


This is quite a jam-packed itinerary so you’ll need to get up quite early each day to account for the long drives in-between some of the stops.


If you’re flying into Portland and hiring a car, it’s a relatively straight forward drive to Cannon Beach. Once you get through Portland, you’ll pick up Highway 26 west to Cannon Beach for 73 miles. At the end of this highway, you’ll merge onto Highway 101 (the Oregon Coast Highway) which will take you to Cannon Beach.

The whole drive from Portland takes around 1 hour 40 minutes. Although today is most likely a travel day, depending on what time you arrive, you may be able to catch sunset on Cannon Beach.

Where to stay in Cannon Beach

There are some lovely places to stay in Cannon Beach, from oceanfront hotels to guest houses and campgrounds. Here are my top picks:

  • Tolovana Inn: We stayed here and I can’t recommend it enough! It’s right on the beach but as it’s a bit further down it’s more affordable than other oceanfront hotels. The staff were so helpful and the rooms were modern and so comfortable. In the morning, we walked out of the hotel and straight onto the beach. It was such good value for money. Check prices > 
  • Surfsand Resort: This is another oceanfront hotel but it is closer to the haystack so it’s more expensive than Tolovana Inn. If you’re celebrating a special occasion then have a look at their ocean view rooms. Check prices >  
  • Wright’s for Camping: This is a great option if you’re planning to drive and camp. It’s a family-run campground offering affordable camping close to the beach. The campground is only open from May to October. Check prices >      

7 Day Oregon Road Trip Itinerary - Cannon Beach


Wake up early and get ready for a busy day of exploring beaches and sand dunes along the Oregon coast!

First Stop: Cannon Beach

If the weather is on your side, I recommend getting up early and going for a sunrise walk along Cannon Beach. It’s such a lovely way to wake up and means you’ll get to experience the beach before it gets too busy. When we went, sunrise was at 7.15am and we were two of the only people on the beach. Watching the sun light up the famous Haystack Rock was incredible.

If you love photography, walk up the steps which are opposite the Haystack Rock (leading up to the houses and beachfront hotels). This will give you a lovely view looking down at the Haystack Rock. It’s a classic view so you’ve probably seen it on Instagram but it really is worth the hype.

After you’ve finished walking along the beach, wander into the town and grab some breakfast. Cannon Beach Bakery and Lazy Susan Café are great options. The town itself is very quaint so it’s worth popping into a few of the local stores.

Cannon Beach - Things to do in Oregon

Second Stop: Ecola State Park

  • Driving time: 11 mins (4.6 km/ 2.9 miles)

The next stop is Ecola State Park. It’s only a 10 minute drive north of Cannon Beach and is a lovely area to explore. Set in a lush rainforest, Ecola State Park is home to old-growth trees, pristine beaches and stunning coastal views.

There are a number of great hikes in the park, such as Ecola Point to Crescent Beach (1.25 miles) and Clatsop Loop (2.8 miles). Ecola Point to Indian Beach (1.5 miles) is another lovely trail. If you’re short on time (remember you do have a long drive ahead of you!) or don’t fancy hiking too far, you can drive to Ecola Point. From there, it’s a very short walk to the viewing area where you can see Haystack Rock, Cannon Beach and the smaller sea stacks jutting out of the ocean.

You will need an Oregon State Parks pass, Oregon Pacific Coast Passport, or a $5 day-use pass to park and explore the trails. You can purchase the day pass using the machine at the car park.

7 Day Oregon Road Trip Itinerary - Ecola Point

Third Stop: Cape Kiwanda

  • Driving time: 1 hour 30 mins (106 km/ 66.3 miles)

Now it’s time to head to Pacific City! This area is home to Cape Kiwanda State Natural Area, one of the most beautiful photography spots on the Oregon coast . It’s known for its stunning cliffs, sandy beaches, and rugged beauty. It even has its own version of Cannon Beach’s Haystack Rock which you can see from Pacific City Beach.

There are a lot of amazing places on the way from Cannon Beach to Cape Kiwanda. If you have an extra day I recommend splitting day 2 into two days so you can visit these spots along the way:

  • Oswald West State Park
  • Elk Flats Trail  

The highlight of Cape Kiwanda is the massive sand dune which separates Pacific City Beach on the south side from McPhillips Beach on the north side. You can climb up to the top for amazing views over both beaches but be warned it is steeper than it looks. Please also pay attention to the signs and do not venture too close to the fragile edges of the cliffs.

If you’re visiting at low tide, you can walk between the sandstone arches on the north side of the cliffs. You can access this area by walking all the way down McPhillips beach towards the sand dune, or by climbing up and over the sand dune from Pacific City Beach. Do not try and access this area when the tide is in as it is incredibly dangerous and you risk getting stranded or caught by sneaker waves. You can check the tide times here .

7 Day Oregon Road Trip Itinerary - Cape Kiwanda

Fourth Stop: Lakeside (Optional)

  • Driving time: 2 hours 44 mins (200 km/ 124 miles)

We really wanted to see the sand dunes on our 7 day Oregon road trip. There are a lot of different sand dunes along the coast but we wanted to see the larger ones which are located further south near Lakeside. If you’re not worried about seeing them you don’t need to drive all the way down to Lakeside. Instead I would stay overnight in Cape Kiwanda. That way, you can take your time driving from Cannon Beach to Cape Kiwanda and explore some of the other stops I mentioned above on day 2 instead.

If you do want to see the John Dellenback Sand Dunes, Lakeside is a good place to stay overnight. The dunes are only open from 7am to 7pm so it’s unlikely you’ll get there in time on day 2 but you’ll be close by for the next day. I recommend stopping en-route and buying some food for breakfast and lunch for day 3. It’s going to be a long day and you’ll want an early start so having things for breakfast will save you a lot of time.

Where to stay in Lakeside

We actually stayed in Winchester Bay as there weren’t many options available but I wouldn’t recommend the place we stayed (Winchester Bay Inn). Instead, I would suggest staying in Lakeside:

  • Lakeside Holiday Home: If you’re travelling with a group then this is a great option as it sleeps up to 5 people. It has all the amenities you need including a kitchen, washing machine and dryer, BBQ and Wi-Fi. Check prices > 
  • Seadrift Motel & RV Park: This is a good option if you’re travelling with an RV but it is pretty basic. It’s close to the sand dunes and has the essentials. Check prices > 
  • Best Western Salbasgeon Inn & Suites: If you prefer hotels, your best option is the Best Western in Reedsport. It’s a bit further away but is still only a 15 minute drive to the sand dunes. Check prices > 


Get up and have some breakfast while getting ready for another busy day. Once you’ve fuelled up for the day, it’s time to drive to John Dellenback Sand Dunes. From here, you’ll then drive into central Oregon to explore the Willamette National Forest before heading to Bend for the night. If you haven’t already, I suggest stocking up on food and supplies before you drive through Willamette National Forest. Cell service will be very spotty in this area so you probably won’t have signal for part of today’s drive.   

First Stop: John Dellenback Sand Dunes

  • Driving time: 5 mins (2.9 km/ 1.8 miles)

The John Dellenback Sand Dunes are located in the Oregon Dunes National Recreation Area. These particular sand dunes are the widest stretch of dunes on the Oregon coast so it’s a very unique outdoor experience. What makes them even more special is that they are closed to motorized vehicles. While other areas of the Oregon Dunes National Recreation Area are open to OHVs, this area isn’t so you can walk on them safely.

The best way to explore the dunes is on the John Dellenback Dunes trail head. It’s a 9km loop which takes you through the sand dunes out to the ocean and back but you don’t have to do the whole trail. We knew we had a long day ahead of us so we just did the first couple of kilometres and then turned back.

You need to pay the $5 day-use fee to park here and hike the trail. Despite reading lots of blog posts that said you had to pay in cash (and rushing around trying to find an ATM), you can pay online using your phone. When you arrive, head to the information board and you’ll see the QR code. You can scan that and then follow instructions to get your day pass. Northwest Forest Passes and Interagency Passes are also accepted.

The trail starts from the parking lot and takes you through the coastal forest. After about half a mile, you’ll emerge from the forest onto the sand dunes. Go left and hike up the large sand dune. From here, you’ll get amazing panoramic views over the dune landscape. You can continue on to the ocean or just stay here and take in the sand formations like we did.

7 Day Oregon Road Trip Itinerary - John Dellenback Sand Dunes

Second Stop: Terwilliger Hot Springs

  • Driving time: 2 hours 49 mins (244 km/ 152 miles)

After you’ve finished exploring the sand dunes, it’s time to start the long drive up to Willamette National Forest. I recommend stopping in Eugene (approximately 1 hour 45 mins driving time) to get some lunch and break up the journey.

From Eugene, you’ll take Highway 126 (also known as the McKenzie Highway into the forest. After about 50 minutes, you’ll turn right onto Cougar Dam Road and then right again at the next junction. Keep driving along this road until you reach Cougar Reservoir where the road splits. Go right and keep driving until you reach the parking lot for Terwilliger Springs. This part of the drive can be a bit bumpy so watch out for pot holes.

Terwilliger Hot Springs (also known as Cougar Hot Springs) is a natural hot spring located in the forest. It’s open from sunrise until sundown each day and gets very busy so don’t expect to have this place to yourself unless you’re able to go first thing in the morning! To get to the hot springs, you have to hike an easy 0.5 mile trail through the forest. The entrance fee costs $10 per person for 2 hours and is payable by cash or card at the trailhead which is often manned.

There are a few different hot pools with varying temperatures. The upper pool is the hottest but that makes it the most popular so you may want to try some of the lower pools instead. In the US, hot springs are clothing optional so expect some nudity. Be respectful if you’re taking photos and read up on hot spring etiquette before going.

7 Day Oregon Itinerary - Terwilliger Hot Springs

Third Stop: Koosah and Sahalie Falls

  • Driving time: 41 mins (50.8 km/ 31.6 miles)

Once you’ve finished soaking, head back to the car and drive back up to Highway 126. Turn right onto the highway and continue driving for about 25 minutes until you see the sign Sahalie Falls on the left hand side. There is a small parking area along the side of the road. You’ll need to do a U-Turn to park there so just be careful as cars drive quite quickly along this highway.

Sahalie and Koosah are two beautiful waterfalls which are located in the Willamette National Forest. The 2.2 mile Waterfalls Loop trail offers incredible views of both waterfalls, as well as the McKenzie River rushing through the canyons. I don’t think I’ve ever seen such a blue river before! If you don’t want to do the full hike, you can just walk 5 minutes from the car to Sahalie Falls lookout instead.  

The trail is well-maintained but if you’re doing this 7 day Oregon road trip in spring, I would pack some micro-spikes. There is usually a lot of snow in this area and although the trail will be packed down it can be very icy.

7 Day Oregon Road Trip Itinerary - Koosah and Sahalie Falls

Fourth Stop: Bend

  • Driving time: 1 hour 8 mins (91.4 km/ 56.8 miles)

Once you’ve finished at the waterfalls, it’s time to drive to Bend. It should take about an hour but you can always stop in the town of Sisters on the way if you need gas, food or a rest break. You’ll probably arrive in the evening so I recommend checking into your hotel and going out for some food. Tomorrow, you’ll have a more relaxing day and will be able to explore Bend properly.

Where to stay in Bend

There are plenty of options to choose from in Bend. Here are a few ones that I’d recommend:

  • The Riverhouse on the Deschutes: Located just north of the town centre on the river, the Riverhouse is a great place to stay if you’re visiting Bend and want somewhere peaceful to relax. We stayed here on our 7 day Oregon road trip and I can’t recommend it enough. Check prices >
  • Campfire Hotel: This boutique hotel is a great affordable option if you’re travelling on a budget. The rooms have everything you need and there is also an outdoor pool, hot tub and fire pit. If you’re looking for a more sociable atmosphere then this is a good place to stay. C heck prices >
  • Springhill Suites Bend: Located in the Old Mill District, Springhill Suites is another great place to stay while visiting Bend. It’s also walking distance to the town centre (15 minutes) so you can easily explore on foot and not worry about driving or parking. Check prices >   

Where to stay in Bend, Oregon


After a busy few days of driving, today will be a much slower day so you can relax and rest before hitting the road again tomorrow. Known for its outdoor recreation, craft beer scene, and vibrant arts culture, Bend is a great town to explore. It offers ample opportunities for hiking, biking, skiing, and river rafting depending on the time of year you visit. Here are a few fun things to do in Bend:

Explore the town

Bend’s downtown area is bustling with unique shops, art galleries, and local eateries serving up delicious farm-to-table cuisine. Explore the town centre and then wander down to Drake Park and walk along the river. Check out the Old Mill District and grab a coffee from Sisters Coffee.

Try local beers

Bend is known for its microbreweries, making it a popular place for beer lovers. Deschutes Brewery is renowned for its iconic Black Butte Porter and offers tours and tastings. For something a bit different, try Boneyard Beer which has lots of innovative brews. 10 Barrel Brewing Co. is another great spot offering a lively atmosphere and wide selection of beers. Other notable breweries include Silver Moon Brewing and Bend Brewing Co.

Hike up Pilot Butte

This large, cinder cone is visible from almost anywhere in town. Formed over 190,000 years ago from a volcanic eruption, Pilot Butte offers panoramic views of Bend and the surrounding Oregon landscape. It’s a 2 mile round trip and usually takes about an hour to hike there and back. If the weather is on your side, aim to hike up Pilot Butte for sunset and enjoy 360 degree views in golden hour.

Visit Tumalo Falls

Located about 20 miles outside of Bend, Tumalo Falls is a stunning, 89-foot tall waterfall. To get there, take Skyliners Road from Bend and follow the signs. The falls are visible from the parking lot and a short hike will take you down to the base of the falls. For a longer hike, take the Tumalo Falls Trail, a 7.5 mile loop that offers beautiful views of the waterfall and surrounding wilderness. The trail is moderately challenging and you’ll enjoy lush forests, cascading creeks, and panoramic vistas on the way.  

Check out Mount Bachelor

Mount Bachelor is a stratovolcano in the Cascade Range of Central Oregon. In winter, it offers world-class skiing and snowboarding on its expansive slopes. It’s also a great spot for snowshoeing, snow tubing and dog sledding. In summer, the mountain transforms into a playground for hiking and mountain biking.

For more things to do in Bend, check out Visit Bend’s website.

7 Day Oregon Itinerary - Bend


Today is going to be quite the adventure! If the weather is nice, get up early, grab some breakfast and head to Smith Rock State Park for a sunrise/ early morning hike. Consider packing some breakfast to eat on the trail and some food for the drive through Mt. Hood as there aren’t a lot of places to stop.

First Stop: Smith Rock State Park

  • Driving time: 30 mins (42 km/ 26 miles)

Located just 30 minutes from Bend, Smith Rock State Park is one of the most unique spots on this 7 day Oregon road trip. The park is one of the 7 wonders of Oregon and boasts towering rock formations carved by the Crooked River, creating a dramatic landscape of cliffs and canyons. The park’s unique geology makes it a popular spot for rock climbing and hiking.

Important information about Smith Rock State Park

You need to pay the $5 day-use fee to park here and hike the trail. When you arrive, head to the information board and you’ll find the pay machine.

There are rattlesnakes in some parts of the park, particularly near the river, so keep your eyes peeled. In summer, they will hide under rocks to keep cool so just be mindful. I also recommend reading up on trails before you hike and checking in with the visitor centre as people report snake sightings to them. Seek medical attention immediately if you are bitten.

The best way to experience the park is to do one of the hiking trails. Rim Rock Trail (0.5 miles) is a great easy hiking option and circles the ridge of the park. You’ll get sweeping views and the trail is relatively flat so it’s a good one for kids. Another good option is Canyon Trail (1.5 miles) which takes you down to the river.

If you’re a keen hiker and are up for something more challenging, I highly recommend the Misery Ridge and River Trail (4 miles). It is an uphill grind but it will take you up to Misery Ridge where you’ll get panoramic views over the park and out to the Cascade Mountains. This is a great hike to do for sunrise or sunset depending on when you visit.

Best hikes in Bend at Smith Rock State Park

Second Stop: Trillium Lake (Seasonal)

  • Driving time: 1 hour 44 mins (137 km/ 85.3 miles)

Head north on Highway 97 for about 10 minutes and then merge onto Highway 26. This will take you all the way to Mount Hood National Forest. It’s a beautiful drive through dense forests and towering peaks. Home to the iconic Mount Hood, the highest point in Oregon, this area is a popular spot for hiking, camping, fishing and skiing. On this 7 day Oregon road trip, you’ll only have time to explore Trillium Lake. However, if you have more time you could add on an extra day and explore more of Mount Hood.

Trillium Lake has a beautiful view of Mount Hood and is incredibly picturesque. This is a great place to have lunch and stretch your legs. There are vault toilets and picnic tables. If you feel like it, you can also do the easy 2-mile Trillium Shoreline Look Trail.

If you’re travelling in spring, be aware that the road may not be accessible. When we went in March there was a lot of snow along the highway and it was blocking the entrance down to Trillium Lake. We weren’t able to make it down to the lake even though we had a SUV. Before starting your trip to Mount Hood, check the National Weather Service’s website for up-to-date information on current snow conditions.

Trillium Lake in Oregon

Third Stop: Hood River

  • Driving time: 59 mins (68 km/ 42.3 miles)

Now it’s time to head north to Hood River! This will be your final destination for the day, but if you’re making good time, feel free to stop at any other points of interest along the way.

Hood River is a picturesque city located on the Columbia River and is renowned for windsurfing, kiteboarding, hiking and mountain biking. Aim to arrive here by late afternoon so that you can explore the area before dinner. The Indian Creek Trail and Hood River Waterfront Trail are both lovely walks. Another great option is Panorama Point. This park is handicapped-accessible. You can drive up to this viewpoint and enjoy panoramic views of Hood River Valley, including Mount Hood and the numerous wineries and orchards.

There are also plenty of vineyards and tasting rooms such as Phelps Creek Vineyards, Cathedral Ridge Winery, and Hood Crest Winery. For a fun evening activity, book a wine and bike tour with MountNbarreL .

If you’re doing this 7 day Oregon road trip in June or July, don’t miss the Hood River Lavender Farms. They grow and produce local and organic lavender products such as essential oils and soaps. The lavender usually blooms in late June and you can pick your own lavender for $10.

Hood River is also home to Mount Hood Railroad . This is one of the best attractions in Hood River for kids and adults alike. You can take the hour-long train ride from downtown into Hood River Valley. It’s a scenic journey through the Columbia River Gorge past orchards and vineyards.

Where to stay in Hood River

Hood River has a range of accommodation options. Here are a few recommendations:

  • Hood River Hotel: This historic hotel is one of the oldest spots in Hood River. Located in the centre of downtown, Hood River Hotel is a great base for exploring the local restaurants, breweries and wineries. They’re actually the sister hotel of Campfire Hotel in Bend so you may be able to get a discount if you book both. Check prices >
  • Sunset Motel Hood River: This is a great option if you’re travelling on a budget. Sunset Motel Hood River is a bit further from the town but is located close to the highway which makes it an ideal place to stay. Check prices >
  • Tucker Park Campground: If you’re looking to camp, Tucker Park Campground is a good option. All campsites at Tucker Park are available on a first-come, first-served basis between May 1 and October 31. The campground is closed between November 1 and April 30. Check prices >

View of Mount Hood from the Columbia River


You’ll be exploring one of my favourite parts of Oregon today – the Columbia River Gorge. Spanning over 80 miles, Columbia River Gorge serves as a natural boundary between Oregon and Washington. It’s another of Oregon’s 7 wonders and for a good reason! The Columbia River Gorge is home to unique geological features and scenic vistas. With over 90 waterfalls scattered throughout the area, the Gorge is often referred to as the ‘waterfall wonderland of the Pacific Northwest’.

There are so many incredible waterfalls on today’s drive along the I-84. Some are very accessible (viewpoints close to the parking lot) while others require you to hike in. You can stop at as many as you like but here are my suggestions based on our own 7 day Oregon itinerary.

Waterfall permits

If you’re visiting between May and September, you will need a timed permit to visit most of these waterfalls. You can find more information here . 

First Stop: Wahcella Falls

  • Driving time: 25 mins (37 km/ 23.3 miles)

This was probably my favourite waterfall in the Columbia River Gorge. The short 1.9 mile out-and-back hike leads you through the lush canyon to the two-tiered waterfall. It’s a fun and scenic hike but it can be quite slippery if there has been a lot of rain so make sure you have shoes with good grip. It costs $5 USD to visit. You can pay online by scanning the QR code once you arrive at the car park.

Oregon road trip itinerary - Wahclella Falls in the Columbia River Gorge

Second Stop: Multnomah Falls

  • Driving time: 11 mins (14.8 km/ 9.2 miles)

Head back onto the Historic Columbia River Highway and drive 10 minutes west to Multnomah Falls. This is one of the most accessible waterfalls in Columbia River Gorge so it can get quite crowded. The parking lot can fill up quickly in the summer months and on weekends so you may have to drive to another waterfall and try again later.

From the car park, cross over the road and the viewing platform is straight ahead of you. This two tiered waterfall is an iconic sight and is the tallest waterfall in Oregon. If you want a different perspective you can hike 0.2 miles up to the Benson Bridge or 1.2 miles to the top of the falls. We decided to just enjoy the view from the main viewing area as we wanted to see quite a few different waterfalls.

Oregon road trip itinerary - Multnomah Falls in the Columbia River Gorge

Third Stop: Latourell Falls

  • Driving time: 12 mins (9.5 km/ 5.9 miles)

The final waterfall on today’s list is Latourell Falls. You can walk down to the base of the waterfall (less than 5 mins) or you can opt to do the 2.4 mile round trip hike to see the upper falls as well. At the base of the waterfall there is a lovely bridge which is great for photos with the waterfall in the background. This particular waterfall can be very busy as it’s one of the closest ones to Portland so be prepared for crowds in the summer and at weekends.

The best things to do on an Oregon road trip

Fourth Stop: Portland

Once you’ve finished exploring the Columbia River Gorge, it’s time to drive back towards Portland. If you’re flying out of Portland, it makes sense to stay here overnight and explore a bit of Portland before you leave. However, if you’re travelling back to Vancouver or Washington, you might want to drive further north and stay closer to Seattle. We decided not to stay in Portland and instead continue up to Olympia for two reasons. Firstly, accommodation was a lot cheaper and secondly, we wanted to shorten the long drive back to Vancouver. It’s completely up to you and will depend on where you’re travelling back to.

Where to stay in Portland

If you decide to stay overnight in Portland, here are a few hotel options:

  • The Mark Spencer Hotel: Located in Portland’s Pearl District, this boutique hotel is just steps from all that Downtown Portland has to offer. Check prices >
  • Courtyard by Marriott Portland City Center: This hotel is also in the Pearl District. It’s on the pricier side but has fantastic amenities and is also pet friendly. Check prices >
  • Econo Lodge City Center: Located further south, this is a great budget option. It’s close to Portland State University and is good value for money. Check prices >


It’s time to head home! Depending on where you’re travelling back to, you could explore Portland in the morning before your flight home. If you’re driving back to Washington or Vancouver, you could stop in Seattle or explore some beautiful spots in Washington, such as Snohomish, Bellingham or Chuckanut. If you have a few extra days, I highly recommend extending your road trip and visiting Olympic National Park in Washington. With ancient rainforests, rugged coastal beaches, and unique ecosystems, it’s an amazing place to explore.


This 7 day Oregon road trip will give you a taste of the state’s epic scenery. If you have more time and want to see more of Oregon, you could continue on to some of the below destinations:

  • Silver Falls State Park
  • Umpqua National Forest (Toketee Falls and Umpqua Hot Springs)
  • Samuel H. Boardman State Scenic Corridor
  • Crater Lake National Park

7 Day Oregon Road Trip Itinerary


Oregon really does have it all and I can’t wait to go back and explore more of this state. I hope this guide helps you plan your own Oregon road trip. If you have any questions, please drop them in the comments and I’ll do my best to answer them!

Where to explore next?

If you’re looking for more North America travel inspiration, have a look at these guides:

  • A complete guide to Capitol Reef National Park
  • Exploring Zion and Bryce Canyon: An epic 3-day road trip itinerary
  • How to spend a weekend in Bryce Canyon

British Columbia

  • 7 Amazing places to visit on Vancouver Island
  • North Vancouver Island: An amazing 4-day road trip itinerary
  • The ultimate Vancouver to Banff road trip itinerary
  • The Best of Banff: The complete 4-day itinerary
  • How to explore Banff and Jasper without a car
  • Driving the Icefields Parkway: The stops you can’t miss

Love from Steph

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Oregon Road Trip Itinerary

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Best places to visit in oregon.

Oregon offers some of the West Coast's most captivating scenery. Moody coastline, lush mountains and mesmerizing waterfalls are abundant, and lucky for travelers, many are easily accessible from nearby towns and cities. U.S. News took into account dining – another one of the state's standout attributes – as well as affordability, sights, traveler sentiment and expert opinion to come up with the best places to visit in Oregon. Want to put in your two cents? Be sure to vote below to influence next year's list.

Crater Lake National Park

Cannon beach, willamette valley, silver falls state park, newport, or, portland, or, john day fossil beds national monument, seaside, or, florence, or, mount bachelor, oregon dunes national recreation area, newberry national volcanic monument.

how to travel to oregon

Formed 7,700 years ago after Mount Mazama erupted and collapsed, Crater Lake is America's deepest lake and makes for a superb lake vacation . Today, you can admire Crater Lake National Park's rich blue water and towering mountains during a boat or trolley tour, a scenic drive along the rim or a hike on one of its many trails. In winter, some roads are closed and visibility may be poor due to clouds and snowstorms. But if you don't mind these potential drawbacks, you can enjoy fun winter activities like sledding, skiing, snowboarding and snowshoeing.

how to travel to oregon

A top destination on the Oregon Coast, Cannon Beach features a nearly 4-mile-long shoreline with tide pools and sand dunes in addition to its most well-known attribute, the 235-foot-tall Haystack Rock. Once you've gotten your fill of this breathtaking beach, hop in the car and visit nearby Oswald West State Park, which offers great hiking, surfing and fishing opportunities. Or, stay in town to check out Cannon Beach's art galleries and watch experts make glass art at Icefire Glassworks.

how to travel to oregon

Powder hounds and nature lovers take note – Mount Hood is one of Oregon's best places to enjoy outdoor activities. The state's tallest mountain towers more than 11,000 feet above sea level and is reputed to be the second-most climbed peak in the world. Its perpetually snow-covered peaks are home to six ski areas that offer the longest ski season in North America, with Timberline Lodge open 10 months of the year. You can also ski after dark at Mount Hood Skibowl, which boasts the nation's largest terrain for night skiing. In the warmer months, take a scenic hike or drive through the mountain's forest.

how to travel to oregon

Willamette Valley is to Oregon what Napa Valley is to California. This destination is home to two-thirds of Oregon's wineries and vineyards, totaling more than 700 wineries for the entire region. Come here to wine and fine dine for days, and be sure to sample as much pinot noir as you can, since it is Willamette Valley's specialty. When you're not wine tasting, enjoy a relaxing soak in one of Willamette Valley's hot springs.

how to travel to oregon

Oregon's largest state park is one of the state's most unique and scenic natural attractions because of its jaw-dropping waterfalls. The Trail of Ten Falls hiking path loops through the park and takes you above, below and even behind its 10 waterfalls, including the 177-foot-tall South Falls. What's more, Silver Falls State Park offers 35-plus miles of backcountry trails that can be used for mountain biking, horseback riding and hiking. When you've worked up an appetite, venture to the park's South Falls Day-use area to enjoy a picnic or barbecue lunch.

how to travel to oregon

Hood River's location in the Columbia River Gorge makes it a prime place for outdoor pursuits. The 80-mile-long valley is known for its stunning collection of waterfalls (think: Multnomah Falls and Starvation Creek Falls) accessible via various hiking trails. It's also considered the windsurfing capital of the world and an excellent destination for other water sports like kiteboarding and sailing. After a long day of adventuring, travelers can unwind with a beer or two at one of the town's microbreweries.

how to travel to oregon

If you're after hearty hikes and delectable eats, Bend is the place for you. This small city has a dining scene that foodies fawn over, complete with food carts, breweries and even cider houses. Bend is also a jumping-off point for numerous natural attractions, including the Deschutes National Forest, which features multiple rivers, mountains and scenic byways. Ample opportunities for outdoor recreation like skiing and snowboarding in winter, hiking in summer and rock climbing in spring and fall make Bend appealing year-round.

how to travel to oregon

Of all of the cute coastal towns Oregon has to offer, families will probably appreciate Newport the most. The town, located on Oregon's central coast, features kid-friendly attractions like the Oregon Coast Aquarium, Oregon State University's Hatfield Marine Science Center and several beaches. Newport also provides numerous outdoor attractions suited for adults, including scenic Yaquina Head Outstanding Natural Area and the equally picturesque Ocean to Bay Trail.

how to travel to oregon

Located on the southern Oregon Coast just 6 miles north of the California border, Brookings offers outdoorsy travelers the perfect Pacific Northwest welcome, with rugged coastline views and natural splendor to explore. Head to Harris Beach State Park for its sandy beach, tide pools, tufted puffins and views of sea stacks on the shoreline. Then, drive up the coast on the Samuel H. Boardman State Scenic Corridor for 12 miles of breathtaking ocean vistas. While the town itself is small, you can catch a movie at the local cinema, grab a beer at Chetco Brewing Company or stroll through Azalea Park.

how to travel to oregon

Portland has one of the most dynamic (and affordable) food scenes in the USA, so you'll likely spend the bulk of your time enjoying the city's many culinary offerings, from Voodoo Doughnut to Eastern European fare at Kachka. In between meals and snacks, visit one of Portland's many parks or cultural sights, such as Forest Park (one of the largest urban parks in the country),  the Portland Art Museum (the oldest art museum in the Pacific Northwest) or Powell's City of Books (the largest independent bookstore in the world).

how to travel to oregon

Fans may recognize Astoria as the setting of "The Goonies," and you'll find several iconic film sites in town, such as the original Goonies house and the Oregon Film Museum, which was featured in the opening scene. But beyond its film history (more than a dozen movies have been filmed here), Astoria holds rich heritage. Its location on the Columbia River near the Pacific Ocean made it a prime fur trading post in the 1800's, and many of Astoria's attractions are dedicated to maritime history. Today, visitors can take in the town's Victorian houses, climb the 125-foot Astoria Column or dine at local breweries and bistros.

how to travel to oregon

As its name suggests, this protected area is famed for having one of the most complete fossil records in the world, spanning more than 40 million years. Visitors can hike through and explore fossils and rock layers in the park's three separate units. Sheep Rock Unit, home to the monument's visitor center which features exhibits and a working lab, is the best starting point. But you won't want to miss the Painted Hills Unit, which woos visitors with distinguishing layered rocks, and the Clarno Unit, which boasts jutting Palisades (rock towers formed from volcanic mudslides).

how to travel to oregon

Seaside is an exceptional vacation destination because it's a gateway to some of the most notable attractions on the Oregon Coast. From this small town of less than 8,000 residents, visitors can reach Tillamook Head, Ecola State Park and Lewis and Clark National Historical Park. All can be found within 15 miles of Seaside, presenting plenty of opportunities for hiking and wildlife viewing. Seaside also offers several can't-miss attractions, such as a beachfront promenade, the Seaside Aquarium and Captain Kid Amusement Park.

how to travel to oregon

Florence appeals to travelers keen on spending their next vacation outdoors. One of this coastal town's best assets is its proximity to Oregon Dunes National Recreation Area, but Florence is worth a visit in and of itself. Visitors can explore Sea Lion Caves, the largest sea cave in the country, ride horses on the beach, fish on the area's many lakes and play golf on a coastal course. Don't forget to save time for visiting the Heceta Head Lighthouse and Historic Old Town Florence, where you'll find shops, art galleries and the Siuslaw Pioneer Museum.

how to travel to oregon

With 4,300-plus skiable acres and the highest skiable elevation in the state, Mount Bachelor is one of the country's top ski destinations . While there are plenty of trails for experienced skiers, Mount Bachelor also offers runs designed for beginners, as well as free and discounted ski lift tickets for first-timers. The mountain, which is a dormant volcano about 20 miles southwest of Bend, receives an average of 462 inches of snowfall annually from late November to May. The fun doesn't stop after ski season, though, when visitors can trade their ski poles and snowboards for mountain bikes and hiking shoes.

how to travel to oregon

This endless sea of sand is best described as otherworldly. In fact, this locale inspired Frank Herbert to write his sci fi book, "Dune." To catch an eyeful of the park's tallest dunes, hike the John Dellenback Dunes Trail. Once you've exhausted yourself from walking on dry sand (trust us, it won't take long), opt for a high-speed ATV or dune buggy ride, or hop on a sandboard. Then, enjoy some shade in the coastal forest at Tahkenitch, or look for wildlife at the Dean Creek Elk Viewing Area.   

how to travel to oregon

Foodies and outdoor lovers will love visiting Tillamook. This small town in northwestern Oregon is an outdoor recreation hub where you can enjoy hiking, kayaking, crabbing, clamming and fishing, among other activities. After an active day, you'll find no shortage of places to satisfy your appetite. Tillamook is perhaps most famous for its dairy industry, so no trip here would be complete without touring the Tillamook Creamery and sampling its cheese and ice cream. Also save time for trying local brews at one of downtown Tillamook's breweries.

how to travel to oregon

Situated roughly 12 miles south of Bend in the Deschutes National Forest, Newberry National Volcanic Monument features one of Oregon's most unique landscapes. The monument's nearly 55,000 acres are filled with lava flows and other fascinating geological features, including a lava river cave and a lava field where NASA astronauts trained to walk on the moon in the '60s. There's also Paulina Peak, which you can climb to the top of for incredible views. When you're not hiking, go biking, boating or fishing.

Vote to Add these Destinations to the Rankings

how to travel to oregon

Lincoln City

how to travel to oregon

Columbia River Gorge National Scenic Area

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Portland and beyond: 8 of the best places to visit in Oregon

Margot Bigg

Apr 17, 2024 • 6 min read

how to travel to oregon

Here are the unmissable places to visit in Oregon © Francesco Vaninetti Photo / Getty Images

Although many people think of Oregon as one big forest — or equate the Pacific Northwest  with Portland , its unabashedly weirdest and biggest city — this massive state offers so much more.

Whether you’re a fan of outdoor adventure, or more into food and wine, you’ll find plenty to experience in Oregon. Here's our guide to the best places to go and why you should spend your time there.

Crowds line up to buy food at street carts

1. Portland

Best place for foodies

Portland is most people’s introduction to Oregon, and as the largest (and quirkiest) city in the state, it’s got plenty to see and do. It’s where you’ll find the state’s best museums and public parks, and the celebrated  Powell’s City of Books is located right in the heart of the city. Portland is also a nationally recognized culinary hub, and plenty of people travel to the City of Roses with one activity in mind: eating. While it is known for its street food scene, with hundreds of  food carts all around town, Portland also has a swankier side, with high-end restaurants such as the James Beard Award-winning Haitian spot  kann drawing in visitors from across the USA and beyond. There is hardly room to do justice to all the wonderful places to eat in Portland in this article, so check out our suggestions for all the best locally-owned and loved restaurants in Portland.

Insider tip: If you’re planning a food trip to Portland, be aware that many local restaurants are closed on Mondays and Tuesdays.

2. The Oregon Coast

Best place for scenic drives

Another one of Oregon’s particularly gorgeous areas, the Oregon Coast is not your average beach destination. Throw out all notions of long days lounging on hot sands and instead embrace the opportunity to enjoy nearly 400 miles of public-access coastline fringed with massive cliffs topped with windswept conifers and huge expanses of sand virtually devoid of loungers and tawdry beach cafes. Nature and scenery are the big draws here, with numerous natural areas and state parks – including the  Cape Perpetua Scenic Area and  Humbug Mountain State Park – enticing hikers and campers.

Planning tip: While you can theoretically drive the Oregon Coast in a day, it’s wise to give yourself a bit more time to explore. This is a region that merits slow drives and lots of extra time to pull over and take in the scenery.

Ready to plan your trip to Oregon? Here are the best things to do while you're there

Two hikers stand at the base of a waterfall looking upwards

3. The Columbia River Gorge

Best place for hikers

While it would be unfair to say that one part of Oregon is the most scenic, the  Columbia River Gorge is definitely up there. Straddling both the Oregon and  Washington sides of the Columbia River (which forms a partial border between the two states), the Gorge as it’s affectionately shortened to, is a fantastic place for day hikes, and most trailheads are within a 30- to 45-minute drive from downtown Portland. Even if you aren’t feeling like exerting much energy, it’s worth visiting to check out Multnomah Falls (the highest waterfall in the state) or to take in the views from the  Vista House , a rest area built in the art nouveau style.

Planning tip: Summer weekends in the Gorge get incredibly crowded and are best avoided if possible. If you don’t have any other options, arrive as early as you can to make sure you can at least snag a parking spot.

Best place for runners and cyclists

Nicknamed “Track Town USA,” Eugene is considered a de facto capital of track and field, and it hosts numerous running events, particularly in the summer. It’s also a great place for more casual joggers, with numerous trails and a mix of hilly and flat terrain. Cyclists will find that the college city’s numerous bike lanes – including the Ruth Bascom Riverbank Trail System, which runs through sprawling  Alton Baker Park – make it easy to get around town on two wheels.

A person harvests bunches of grapes for winemaking

5. The Willamette Valley

Best place for wine lovers

You don’t need to venture to  France or  Italy  — or even to California’s  Napa Valley  — to immerse yourself in all things viticulture. Oregon’s  Willamette Valley is among the best places to go wine tasting in the country. This region, which runs from just south of Portland all the way to Eugene, has all the trappings of a postcard-perfect wine destination, complete with rolling hills covered with vine plantings, lovely bistros, and loads of comfy-cozy bed and breakfasts. Best of all, tasting fees tend to be a little lower than in some other parts of the country, and are typically waived if you buy a couple of bottles or more. If you're thinking about a trip to Willamette Valley, check out our first timer's guide to the region.

Planning tip: Visit in the late summer for great weather and to see grapes on the vines. If you do end up coming during the harvest season (usually in September and October) expect some delays due to slow-moving farm equipment on country roads.

Best place for all-weather adventurers

The Central Oregon city of  Bend is a magnet for outdoorsy folk, and its position east of the Cascade Mountains means that the climate is a bit drier and sunnier than what you’ll find in the western reaches of the state. Bend draws in skiers and snowboarders in the winter due to its proximity to Mt Bachelor, but it’s a particularly great base for summertime adventures. Popular activities range from rafting the Deschutes River to setting off on backpacking adventures in the  Three Sisters Wilderness . Bend is also just a short drive from  Smith Rock , one of the top destinations in the state for rock climbing.

Time your visit to Oregon just right with our seasonal guide

View of a snow-covered island in an alpine lake

7. Crater Lake National Park  

Best place for lake lovers

Protecting the deepest lake in the country,  Crater Lake National Park is the only national park in Oregon. It's worth taking a boat ride out to  Wizard Island , a cinder cone islet in the center of the caldera, and going for a spin  along Rim Drive, a 33-mile loop that offers motorists (and cyclists) the chance to see Crater Lake from every angle. For particularly great views of the lake and the woods that surround us, take the 3.4-mile hike up to the top of Garfield Peak, accessible via a trailhead at the park's Rim Village.

Planning tip: Crater Lake National Park is incredibly popular, and campsites and lodging at the park fill up well in advance, so book as early as you can. If you can’t secure a spot, nearby Diamond Lake is a good alternative and is within an easy drive of the national park.

Best place for theater fans

A short drive from the  California border, the  Southern Oregon city of Ashland’s biggest claim to fame is the Oregon Shakespeare Festival, a theater company that’s been presenting the works of the Bard himself since launching back in 1935. The season lasts for most of the year, taking a break in the cooler winter months, and features a solid annual lineup of Shakespeare’s classics along with a smattering of plays from other playwrights. For more of the best things to do in Ashland, check out our guide to this fun city.

This article was first published Dec 8, 2021 and updated Apr 17, 2024.

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The Oregon Trail: Yes, You Can Still Go on It

how to travel to oregon

  • Activities and Interests
  • History and Culture
  • National Parks
  • United States National Parks

Spain has the Camino . China has the Silk Road .

The United States has the Oregon Trail.

Despite the fact that this perilous trail was only used by pioneers for a short period of time (between 40-60 years), it remains prominent in the American imagination. That’s largely thanks to haunting tales like that of the Donner Party and early PC games like Oregon Trail .

In 1993, the US National Parks Service decided to celebrate the 150th anniversary of the Oregon Trail by posting road signs across the country. These now mark the roads and parks where the trail’s original migrants would have passed through.

In fact, you can follow these all the way from Independence Missouri to the coasts of Oregon.

That’s right—people are still traveling the Oregon Trail. And the National Park Service is working overtime to make that easier than ever before. Here’s how you can get involved.

Pioneer vibes for the modern traveler

The National Park Service has done a stellar job of mapping out the historical Oregon Trail . This 2,000-mile trail snakes through Missouri, Kansas, Nebraska, Wyoming, Idaho, Utah, Oregon, and Washington.

Along the way, you can see some of the US’s most beautiful and remote landscapes. (Don’t believe the hype—the Great Plains of Kansas and Nebraska are absolutely stunning.)

Want to map out your route along the Oregon Trail? You can do so using these helpful maps from the National Park Service.

  • The Interactive Map lets you zero in on the parks and landmarks that you’ll want to see when road-tripping on the old Oregon Trail.
  • The Things To Do page connects you to sites, landmarks, and other areas that were referenced by actual Oregon Trail survivors. You can even check out wagon ruts sunken into the dirt.
  • The Auto Tour Route Interpretive Guide gives you even more information on how to see the most relevant sites while driving. It’s designed as a booklet that travelers can print out. ( Nerd alert : these PDFs are surprisingly well done—I just wasted an hour reading through them for fun.)
  • The GIS Interactive Map highlights the resources that pioneer travelers would have been concerned with during their journey back in the 1800s. This is a great angle for those who like really like history.

how to travel to oregon

Which Oregon trail sites are worth seeing?

There are dozens of ways to get from Missouri to Oregon. I’ll let you decide how faithful you want to be to the NPS’s guide.

Using the Interactive Map linked above, you can check out the trail sites listed below.

The easiest way to explore what’s on offer is to read through the interactive map on a state-by-state basis.

I skimmed Missouri’s list. It includes locations like the official courthouse in Independence where travelers set off from, small caves tucked away in forests where travelers rested at midday, and the Bingham-Waggoner Estate where you can see ruts from the covered wagons.

I recommend looking into what interests you the most, whether that’s modern museums that cover the Oregon Trail, National Parks where it once passed through, or historical sites. There’s truly something for everyone.

Here are the locations I would keep on my radar:

  • Barnes Enclosure and Cave Spring Interpretive Center
  • Independence Courthouse Square
  • Alcove Spring Campsite
  • Oregon Trail Park at Scott Springs
  • Oregon Trail Park Grave Site
  • The Archway-Pioneer Sod House
  • Homestead National Historical Park
  • Rock Creek Station State Historical Park
  • Independence Rock State Historic Site
  • Split Rock Interpretive Site
  • Bonneville Point
  • Oregon Trail Park & Marina
  • Three Island Crossing State Park
  • Pioneer Woman’s Grave & Trail
  • National Historic Oregon Trail Interpretive Center
  • Birch Creek Trail Site
  • Fort Vancouver National Historical Site

Image of Tay Belgeri

Tay Belgeri is a content writer with global experience. She writes for brands like Santander Bank, PokerStars, DraftKings, and OddsChecker. Her affiliate posts have appeared on AP News, Ranker, Notion, OK! Magazine, and other major sites. She writes about a variety of cultural topics (from sports to high fashion) but specializes in travel. Originally from Missouri, she now lives in Spain. In a few years, she will have spent more time outside the US than inside it. Career highlights: • Selected to present research by the National Council of Undergraduate Research (2014) • Acquired grants for New York City’s first Indigenous Peoples Day Celebration (2015) • Joined OddsChecker’s US Launch team (2020) • Shortlisted for the Foreword INDIES (2021, 2023)

I-5 closure: Here are the best routes to avoid gridlock in Portland this weekend

  • Updated: Jun. 28, 2024, 8:05 p.m. |
  • Published: Jun. 28, 2024, 1:27 p.m.

I-5 closure in SW Portland late June 2024

The Interstate 5 closure of all northbound and southbound lanes between the Southwest Terwilliger and OR 99W/SW Barbur Boulevard exits will begin at 9 p.m. Friday and continue all hours and days through the weekend, with a planned reopening by 5 a.m. Monday. file photo from The Oregonian LC- The Oregonian

  • Beth Slovic | The Oregonian/OregonLive
  • Mark Friesen | The Oregonian/OregonLive

This weekend’s planned closure of Interstate 5 through a portion of Southwest Portland has drivers from Clark County to Eugene — and beyond — fretting about travel plans.

The Oregon Department of Transportation will shut down I-5 at 9 p.m. Friday, June 28, between the Southwest Terwilliger Boulevard exit and the Capitol Highway overpass mileposts 297 to 295, including several onramps . The closure will start at 9 p.m. Friday, June 28, and continue all hours and days through 5 a.m. Monday, July 1.

ODOT is encouraging north-south travelers to use other freeways including interstates 205, 84, OR 217, and U.S. 26 to get around the four-mile closure.

And Portland Bureau of Transportation officials are encouraging people to treat the closure as they would a weather emergency, completing errands before the freeway shuts down, staying home if they don’t have to get anywhere and reserving the roads for people who must travel.

Here are several routes to get around if you must travel in the vicinity of the closure.

Oregon 43 may be a good choice for traveling north or south yet staying off the bigger highways. If your goal is I-5 North, taking the Terwilliger turnoff north of downtown Lake Oswego will take you right to I-5 just north of the closure.

Boones Ferry Road

Heading north on I-5, the Lower Boones Ferry Road exit is one of the last places to get off. It’ll likely be busy, but it will get you right to Terwilliger Boulevard, which will put you back on I-5 just beyond the closure.

I-5 Northbound can be backed up to Wilsonville or farther on the most average of weekends, so if you’re coming from the valley, you might consider taking a drive through the country and going east or west of the freeway, depending on your destination. Taking River Road north out of Keizer will take you through St. Paul (the rodeo starts Tuesday) and up to Oregon 99W at Newberg. Oregon 99E will take you through Woodburn and Canby up toward Oregon City and Milwaukie.

Barbur Boulevard

The last open off-ramps in both directions empty onto Barbur Boulevard. Consequently, it will be very busy. ODOT says to be ready for long delays.

Interstate 205

Interstates 205 and 84 will likely be popular detour routes, especially with those wanting to bypass Portland altogether on their way north or south.

Oregon 217 and U.S. 26 are the standard westside I-5 detour, so expect them to be even more crowded than their usual crowded weekend state. Also note that ongoing construction on 217 will further slow traffic.

Capitol Highway

Capitol Highway might be a good option for getting on to I-5 South just south of the closure. Just be aware that if you’re coming from the south, you can’t turn left into the exit at Southwest Barbur Boulevard. You need to turn right on Barbur and then loop around using Southwest Taylor’s Ferry Road. Follow the signs.

— Beth Slovic is a deputy editor on the public safety and breaking news team. Reach her at 503-221-8551 or [email protected] .

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Bird flu outbreak spreads to mammals in 31 states. At least 21 cats infected. What to know

Among those infected are cows in 12 states, foxes, mice, striped skunks, mountain lions and harbor seals, and alpacas. at least 21 domestic cats in nine states have caught the virus since march 1.

The concerning bird flu outbreak that has spread to four humans so far as it expands quickly in the U.S. has jumped to dozens of species, infecting mammals in at least 31 states.

Among those infected are cows in 12 states, foxes, mice, striped skunks, mountain lions and harbor seals, and alpacas.

At least 21 domestic cats in nine states have caught the virus since March 1, according to the U.S. Department of Agriculture . Cats that have tested positive include feral, barn cats and household pets.

While it's possible a human could become sick from their furry friends, it's not very likely, the CDC says . The H5N1 virus could be spread through cats' saliva, feces or other body fluids. All the people who caught it were exposed on farms and fully recovered, and officials are working to reduce the spread.

Here's what to know.

Virus spreading: Concerns grow as 'gigantic' bird flu outbreak runs rampant in US dairy herds

Can cats get bird flu?

The short answer? Yes, cats can contract bird flu if they interact with infected birds.

Bird flu is primarily considered a transmission risk between wild birds and domestic birds; more recent presence of bird flu in dairy cows is believed to be a first for the species.

Researchers at Cornell University believe the affected Texas dairy cows were infected via water and food sources contaminated by wild birds migrating through the area. It was then likely spread between cows in close quarters.

Dr. Elisha Frye, an assistant professor of practice at Cornell's Department of Population Medicine and Diagnostic Sciences, was called to an affected dairy farm in March to investigate the deaths of cows, birds and cats at the facility. Frye determined the presence of the illness in the cows using milk samples, manure and nasal swabs.

Testing was also done on dead birds found on the farm, as well as one of three cats found dead at the facilities around the same time. All the tests turned up evidence of the presence of bird flu.

"It was kind of the same timeline as when we found it in the cattle samples, but it did kind of link it together," Frye previously told USA TODAY . "The birds, the cat and milk from the cows all having the same pathogen in them made sense at the time for that being the main cause of illness."

Have cats been affected by bird flu in the past?

The CDC has records of sporadic mammalian outbreaks of the bird flu in the past, impacting both wild animals like foxes and bears, as well as pets like dogs and cats. Officials believe these cases are caused by the animals consuming infected birds and poultry.

In 2004, an outbreak in domestic animals including cats and dogs was reported in Thailand, and another outbreak impacting pets occurred in Germany and North America in 2006 . The organization says humans contracting the virus from their pets is very rare and unlikely but has happened as a result of prolonged, unprotected exposure.

In 2016, a veterinarian in New York City contracted bird flu from repeated exposure to sick cats without protective gear. The vet suffered mild flu symptoms.

Signs your pet may be sick

The likelihood of your cat contracting bird flu is minimal. However, it can happen if your cat is often outside and ends up eating or getting too cozy with an infected bird, or hangs out in a contaminated environment.

If you suspect people or animals in your home have been around a sick or dead bird, you should monitor them closely for these signs:

  • Fever or feeling feverish/chills.
  • Sore throat.
  • Difficulty breathing/shortness of breath.
  • Conjunctivitis (eye tearing, redness, irritation, or discharge from eye).
  • Runny or stuffy nose.
  • Muscle or body aches.

How to prevent the spread of bird flu

Avoiding exposure in the first place is the most effective way to stop the spread, says the CDC.

  • Avoid direct contact with wild birds and observe wild birds only from a distance, whenever possible.
  • Avoid contact between pets (e.g., pet birds, dogs and cats) with wild birds.
  • Don’t touch sick or dead birds, their feces or litter or any surface or water source (e.g., ponds, waterers, buckets, pans, troughs) that might be contaminated with their saliva, feces, or any other bodily fluids without wearing personal protective equipment (PPE). 
  • Avoid touching your mouth, nose, or eyes after contact with birds or surfaces that may be contaminated with saliva, mucous, or feces from wild or domestic birds.
  • Wash your hands with soap and water after touching birds or other sick animals.
  • Change your clothes after contact with wild birds, poultry and sick animals.

Contributing: Dinah Voyles Pulver, USA TODAY

Growing wildfire in central Oregon chars 1,700 acres, prompts evacuations

intense smoke oregon Darlene wildfire

A small wildfire in central Oregon quickly spread Tuesday, charring around 1,700 acres by nightfall and triggering evacuations while leaving thousands without power.

The wildfire, dubbed the Darlene 3 Fire, grew quickly on the outskirts of La Pine in Deschutes County, requiring the response of regional firefighters. It was still spreading Tuesday night, according to Central Oregon Interagency Dispatch .

Firefighters responded to the blaze around 12:45 p.m. local time, the dispatch agency said, and officials estimated that it covered 3 to 5 acres. An hour later, the fire had already tripled in size. It swelled to 1,700 acres by Tuesday night and was 0% contained shortly after 9 p.m.

Residents in some areas of Deschutes County were told to evacuate immediately or risk public safety personnel’s being unable to help them. People in other, nearby areas were told to prepare to evacuate.

Photos and videos posted to the Deschutes County Sheriff’s Office Facebook page showed black smoke burning behind several properties.

The U.S. Forest Service shut down and evacuated nearby campgrounds and trails in Deschutes National Forest.

A shelter for evacuees was set up at La Pine High School, and a shelter for livestock and pets was established at the La Pine Rodeo Grounds.

Gov. Tina Kotek invoked Oregon's Emergency Conflagration Act — a law that allows the state fire marshal to invoke the full power of the Oregon fire service to protect life and property.

Midstate Electric Cooperative — an electric utility company — told some customers it would most likely enact a public safety shutoff in the area as a result of the fires.

More than 2,000 customers are without power, according to the company.

The cause of the fire is under investigation.

The fire's name, Darlene 3, is a sign of the area's history with wildfires, according to NBC affiliate KTVZ of Bend . In 2021, the Darlene Fire burned nearly 700 acres and destroyed two homes, the station reported.

La Pine is a rural city about 30 miles southwest of Bend. Its population is around 2,500. The population of the greater La Pine area is just under 20,000. It is the “youngest” city in Oregon, incorporated in 2006, according to La Pine’s website .

Raquel Coronell Uribe is a breaking news reporter. 

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Oregon Football Lands Commitment From 4-Star Athlete Brandon Finney

Matt galatzan | jun 25, 2024.

Jan 1, 2024; Glendale, AZ, USA; Oregon Ducks head coach Dan Lanning celebrates with the trophy after defeating the Liberty Flames during the 2024 Fiesta Bowl at State Farm Stadium. Mandatory Credit: Mark J. Rebilas-USA TODAY Sports

  • Oregon Ducks
  • Penn State Nittany Lions
  • Ohio State Buckeyes
  • South Carolina Gamecocks

The Oregon Ducks were already on a roll in the 2025 recruiting cycle , sitting with a top-10 class, and gaining momentum with multiple top-tier prospects.

But on Tuesday that class got even stronger.

According to reports from On3's Hayes Fawcett , four-star McDonogh School (Owings Mills, MD) athlete Brandon Finney committed to Oregon, picking the Ducks over Penn State, Ohio State, and South Carolina.

“Grateful for the many opportunities, but I’m ready to work GO DUCKS!!” Finney told Fawcett.

Oregon head coach Dan Lanning walks the field during the Oregon Ducks’ Spring Game Saturday, April 27. 2024 at Autzen Stadium

With the commitment from the 6-2, 190-pound Finney, the Ducks now hold 10 commitments in the 2025 class, including nine of those pledges sitting as four-star recruits.

Last year with McDonogh, Finney had 51 receptions for 632 yards and four touchdowns. However, Finney wasn't just a difference-maker on offense. On the defensive side of the ball, Finney also hauled in three interceptions and made 22 total tackles from his corner spot.

Finney is also a track star, running a 10.85 100-meter dash and a 21.84 200-meter dash in his junior season, qualifying for the Maryland Class A state finals, per 247Sports.

As it stands, Finney ranks as the No. 191 overall player, the No. 8 athlete and the No. 4 player in the state of Maryland, per the On3 Industry Ranking, which is a composite ranking of the four major recruiting services. On3 is the highest on Finney individually, ranking him as the No. 131 overall player, the No. 5 athlete and the No. 3 player in the state of Maryland.

He currently projects as a corner at the college level.

Stay up to date on all things Oregon Ducks by visiting  Oregon Ducks on SI  daily and following Oregon Ducks on SI on  Facebook  and  X .

Matt Galatzan



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