boston to portland maine road trip

Boston to Portland, Maine: A Road Trip Itinerary

• Latest Posts

• 21 Family Vacations in New England for Every Season (2024) - February 26, 2024
• 15 Wonderful Weekend Getaways in Maine (2024) - February 3, 2024
• 33 Best Beach Towns in New England to Visit in 2024 🌊 - January 28, 2024

Are you looking for a fun and scenic road trip along the New England coast? If so, consider making the journey from Boston to Portland, Maine . It’s not a long road trip, but this scenic route takes you through charming coastal towns and offers plenty of opportunities for adventure, exploration, and fresh caught seafood, if that’s your jam!

To help you plan your Boston to Portland trip, we’ve put together a New England itinerary that highlights some of the best stops along the way. From Boston, Massachusetts to Portland, Maine, this coastal New England road trip offers a variety of suggestions for where to stop and what to do to make this a very memorable trip!

Table of Contents

How to Get from Boston MA to Portland ME

Do you know that you can easily take a train from Boston, Massachusetts to Portland, Maine?  The Amtrak Downeaster connects Boston and Portland, so if you’d like to skip the driving and just ride direct, that’s not a bad option at all. Amtrak trains can be a very convenient way to road trip, but you will of course miss out on all the fun stops along the way.

However, if you’re looking to get from Boston to Portland, Maine in just a couple of hours without having to slide behind the wheel of your car, you’ve got options. Check out the train schedule here . There are multiple Amtrak trains per day leaving from Boston North Station heading to Portland!

If you’d rather fly than ride, Logan Airport has plenty of flights from Boston to Portland, Maine, too! Jet Blue, American Airlines, Delta, and more fly daily between these two locations. Click here to look for deals on Boston to Portland ME flights !

If you’re the type of person who would prefer to control where you stop and for how long, drive. There is a direct route that takes you up I-95 that would get you from Boston to Portland ME in just under 2 hours, but that’s not for people looking for road trip adventures along the way.

Want the road trip experience but don’t have your own wheels? Click here to find deals on a rental car !

How Far is it from Boston to Portland, Maine?

Not very! Whether you’re traveling by plane, train, or automobile, it’s just about a couple of hours, but if you’re looking to enjoy some of the top sights in coastal Massachusetts and Maine, then it will take a couple of days at least to really get the full experience.

Can you do the drive in one day with quick stops at each spot? Technically, yes. But spreading this coastal road trip between Boston and Portland out over a weekend or longer will be more fun! 

We are including the best things to do at each stop between Boston and Portland and letting you decide where to spend your time during this very customizable coastal road trip.

We suggest allowing 2-3 days for this Boston to Portland ME trip, but you should personalize it any way you’d like. We’re even including our favorite places to stay along the way for overnight fun, too.

Where to Stop on the Drive from Boston to Portland, Maine

Stop 1: salem ma (20.2 miles via us-1n).

Kick off your trip by heading north from Boston to Salem, Massachusetts. Salem is a fascinating town with a rich history, and is worthy of being its own vacation destination, especially if you’re planning an October trip and looking for haunted places to visit and stay ! 

Salem is one of our favorite places to visit and it’s definitely worth a longer visit to take advantage of all the cool ghost and walking tours , but if you’ve only got a few hours to spend in Salem during your Boston to Portland road trip, these are our suggestions for what to see and where to stop:

• Hocus Pocus Filming Locations
• See the Salem Witch House
• Pay your respects at Salem Witch Memorial
• Grab a bite and/or a brew (coffee or beer!) at Gulu Gulu Cafe 

Where to Stay: Hotel Salem

Stop 2: Rockport MA (20.1 miles via MA-128 N)

Next up is Rockport, Massachusetts! Technically, this stop does take you just a bit off the relatively straight path north to Portland, but this charming coastal Massachusetts town is worth the detour, I promise. 

We have loved every visit we’ve made to this gem by the sea; it’s one of those quaint coastal places where you’ll find delicious restaurants, great breakfast spots , unique things to do, and even cool places to stay if you decide to do an overnight. These are our top recommendations for what to do in Rockport:

• Go strolling down and shop Bearskin Neck
• See Motif #1
• Enjoy a lobster roll at Roy Moore Lobster Co

Where to Stay: Emerson Inn

Stop 3: Hampton Beach in Hampton NH (36.9 miles via MA-133 W)

One of the most iconic beaches in New England , Hampton Beach is a definite must-visit if you’re taking a scenic road trip from Boston to Portland ME! In fact, it landed on Country Living’s list of the top eight “classic beach boardwalks” in the US, with the magazine citing the many offerings of Hampton Beach as being a perfect representation of classic summer nostalgia.

Of course, it’s true! Not only is there the beautiful beach with its picturesque boardwalk, but there’s also a lot of non beach fun nearby, like playing arcade games at Funarama, gambling a little at Ocean Gaming Casino, eating some yummy fried seafood, and then heading to Buc’s Lagoon Mini Golf and Ice Cream to play a round and follow up with a frozen treat!

Some must-dos while in Hampton Beach:

• Walk the Hampton Beach boardwalk
• Squish your toes in the soft sand at Hampton Beach State Park!
• Have some fun at Funarama

Where to Stay: Ashworth by the Sea

Stop 4: Portsmouth NH (13.6 miles via NH-1A N/Ocean Blvd)

Portsmouth is one of the top spots to visit on the New Hampshire Seacoast, and should not be missed on your road trip from Boston to Portland, Maine! Portsmouth has plenty of places to stretch your legs, with Strawbery Banke Museum, the historical outdoor museum, and the very walkable downtown with cobblestone streets and lots of great shopping- yay sales tax-free New Hampshire!

If you’re looking for a great place to grab a bite in Portsmouth, there are two notable spots to consider: Fezziwig’s Food & Fountain and Portsmouth Book & Bar . The former is a delightfully whimsical cafe that is perfect for a sandwich, pastries, and tea, and the latter is a bookstore/restaurant/bar that really delivers on all fronts! Both are memorable places to visit and eat in Portsmouth, but there are lots of cool breweries, bars , and breakfast spots to check out too!

Where to go on your Portsmouth stop:

• Enjoy living history at Strawberry Banke Museum
• Stroll pretty Prescott Park (you might even catch a summer concert!)
• Take advantage of no sales tax shopping!
• Grab a bite at Fezziwig’s

Where to Stay: The Hotel Portsmouth

Stop 5: York ME (10 miles via 95 N)

Once you’ve had your Portsmouth fun, head north to York, Maine. One of the coolest coastal towns in Maine, York is known for its beautiful beaches and historic sites and would be a fantastic stop on your Boston to Portland trip.

There’s plenty of great eye candy in York, with Long Sands Beach and Nubble Lighthouse; head to Sohier Park and you’ll have fantastic views of the lighthouse. For history lovers, the Old York Historical Society has impeccably maintained several historic structures, including the Old Gaol , originally built in 1656 as Maine’s first jail.

If you’re hungry in York, you’ve got options, but Fox’s Lobster House has been serving up fresh caught lobster and the finest blueberry pie since 1966, so they’re the place to go for a taste of quintessential coastal Maine!

These are some of the top things to do during your stop in York:

• Walk Long Sands Beach
• Ooh and ahh and photograph Nubble Lighthouse
• Visit the Old Gaol
• Eat at Fox’s Lobster House

Where to Stay: York Harbor Inn

Stop 6: Ogunquit ME (10 miles via US-1 N)

Next stop is Ogunquit, Maine, whose name means Beautiful Place by the Sea in the Algonquin language. This charming coastal town has lots to do and see , including scenic Marginal Way trail, which offers stunning views of the coastline, and lovely beaches that are perfect for sunbathing. 

Visit Perkins Cove, take a walk along the beach (Footbridge Beach is especially picturesque), or visit the Ogunquit Museum of American Art. The Ogunquit Playhouse has been a staple of this area since 1933, so if you can make the time, seeing a show at this iconic spot would be a memory-making activity, for sure. Pair this with a dinner at The Front Porch , the local piano bar/restaurant, and you’d be in for a great evening out in Ogunquit.

These are some of our top recommendations for your Ogunquit stop:

• Stroll Marginal Way
• Enjoy the scenery at Footbridge Beach
• Dine at The Front Porch
• Catch a show at the Ogunquit Playhouse

Where to Stay: Gorges Grant Hotel

Stop 7: Kennebunkport ME (11.7 miles via US-1 N and State Rte 9 E)

Onwards to charming Kennebunkport, Maine . This coastal Maine town is known for its historic homes, quaint shops, and beautiful beaches; a drive by the iconic Wedding Cake House (private property so keep a respectful distance) will confirm! 

Kennebunkport is full of great places to eat and shop, and heading to Dock Square will take you to many of them! This unique waterside area is home to several popular places to visit in Kennebunkport, and the Boathouse Restaurant is one of the most popular local restaurants that offer waterfront dining! 

What to do during your Kennebunkport stop:

• Drive by the Wedding Cake House
• Stroll and shop Dock Square
• Indulge a little at Boathouse Restaurant

Where to Stay: The Boathouse (yes, it’s also a lovely waterfront boutique hotel, too!)

Stop 8: Old Orchard Beach ME (18.2 miles via US-1 N to 95 N)

Next up is Old Orchard Beach, Maine, home to the last remaining beachfront amusement park in New England! Palace Playland has classic arcade games and amusement park rides, including a ferris wheel, roller coasters, and so much more, plus you’ve got beautiful Old Orchard Beach with its 7 miles of sandy beach to enjoy, too.

Another popular OOB attraction is the Old Orchard Beach Pier , home to all kinds of great places to eat, drink, shop, and enjoy that spectacular ocean scenery! Hungry? Grab a bite at Hooligan’s Steak & Ale, the first restaurant you’ll see when walking onto the OOB Pier! 

Must-do’s for your Old Orchard Beach stop:

• Play at Palace Playland
• Walk Old Orchard Beach
• Grab a bite at Hooligan’s on the Pier

Where to Stay: Alouette Beach Resort

Stop 9: Cape Elizabeth ME (17.1 miles via US-1 N)

The next stop on this Boston to Portland ME itinerary is Cape Elizabeth, home to some of the prettiest lighthouses in Maine . Granted, you’re just a few miles outside of Portland at this point, but skipping over a visit to the lighthouses in this lovely spot would be a travesty!

There’s Portland Head Light, the oldest remaining lighthouse in the state, Ram Island Ledge Lighthouse, and Two Lights, Cape Elizabeth Light and its twin, which is now a private residence. Cape Elizabeth is home to beautiful beaches, parks, and one of the best restaurants in Maine : The Lobster Shack at Two Lights.

Things to see in Cape Elizabeth:

• Tour Portland Head Light
• See Cape Elizabeth Light
• Eat at The Lobster Shack

Where to Stay in Cape Elizabeth: Inn by the Sea

Stop 10: Portland ME (8.5 miles via ME-77 N)

Finally, your destination is at hand! You’ve arrived in beautiful Portland, one of the top vacation destinations in Maine, and a town that seems to truly have something for just about everyone . You’ve got museums and art galleries, fun out on the water , shopping and browsing through Old Port, the Portland Observatory , and breweries, bakeries , breakfast spots , coffee shops, and restaurants galore to choose from.

In fact, if you’re a seafood lover, you’re going to LOVE the options you have for seafood in Portland! Check out Luke’s Lobster Shack on the Portland Pier for waterfront dining.

Portland has several great options for where to stay, including conveniently located vacation rentals and hotels , and beautiful boutique hotels that offer a variety of unique experiences, like the Press Hotel , located in the former headquarters of the Portland Press Herald. 

Whether you’re spending a weekend or a day in Portland, you’ll find fun in this popular Maine city by the sea.

What to do in Portland, Maine:

• Stroll Old Port
• Get out on the water
• Tour the Portland Observatory
• Eat some lobstah

Where to Stay in Portland: The Press Hotel

There are many different ways you can choose to get from Boston to Portland, Maine, but if you take the scenic route along the coast, you’ll have so many fantastic memory making opportunities! Coastal New England road trips are the best!

You might also like:

• Ultimate Boston to Acadia National Park Road Trip (2+ Day Itinerary)
• 5 Spectacular Maine Road Trip Routes You Won’t Want to Miss!
• New England Fall Road Trip: 8 Great Itineraries (+Bonus Ideas)
• The Ultimate Maine Coast Road Trip: Kittery to Bar Harbor

New England Wanderlust

Fall , Maine , Massachusetts  ·  September 21, 2022

10 Best Stops To Make When Driving From Boston To Portland, Maine (2024)

Driving From Boson to Portland, Maine is one of the best road trips to take in New England because there’s so much you can see in a very short amount of time. If you’re coming from outside of New England, you’ll definitely want to spend a day or two in Boston before taking this road trip, but if you already live in Boston, the payoff along this is really rewarding.

This post is all about the best places to stop on when driving Boston to Portland, Maine, and in each destination, I’ll share all the best sites to see, restaurant recommendations, and the best places to stay overnight. I even have an itinerary for a day trip from Boston to Portland for those who are really short on time! With that, let’s get into it.

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our  Privacy Policy .

How Long Is The Drive From Boston To Portland, Maine?

This drive can take anywhere from 1 hour and 45 minutes to 2 hours and 15 minutes without any stops, and it all depends on traffic. There’s usually traffic getting in and out of Boston on weekdays, but on weekends, it shouldn’t be quite as bad. I suggest using Google Maps to type in the exact day and time you plan to leave to get a better idea, especially if you’re short on time (taking a day trip, for example).

While most of these suggestions are directly on the way while driving from Boston to Portland, Maine, it will add some extra time, so you’ll want to factor that into your driving time. Once you decide on which stops you want to make (hopefully all of them!), you can then get a better idea of how long your drive will be in total.

Is The Drive From Boston To Portland, Maine Scenic?

It’s very scenic! On this drive, you’ll pass through charming small towns in Massachusetts, visit the best coastal town in New Hampshire, and then begin your drive up the coast of Maine, stopping in some amazing seaside destinations with lots of character and fun things to do.

How Many Days Do You Need When Driving From Boston To Portland, ME?

Anywhere from a day to a week, and it really just depends on how much time you have to dedicate to the trip. This is a really great weekend or long weekend road trip to take, as you’ll have time to stop at most of the destinations on the way there or back. But, I personally suggest about 4-5 days if you have an interest in seeing as much as possible on the drive, and also want a day or two to explore Portland.

For ideas on a day trip from Boston to Portland, keep reading later in the post to see my suggested itinerary!

Overview Of The Drive From Boston To Portland, Maine

There are 10 towns I suggest you stop in while driving Boston to Portland, Maine. They’re all very easy to spend a few hours in before moving on, and depending on how much time you have, you can either do half of them on your way to Portland, and the other half on your way back, or eliminate any that you’ve done before, or don’t have any interest in. Each of these towns is also pretty much on the direct route from Boston to Portland, with minimal diverging off course.

I’ll do a more detailed breakdown of each destination and the best things to do later on, but for now, here’s a breakdown of all the stops you’ll making, including how far they are from one another:

• Salem, MA (30-45 minutes from Boston, depending on traffic)
• Rockport, MA (optional stop because it’s a bit out of the way, 30-40 minutes from Salem)
• Newburyport, MA (40 minutes from Salem, or 45 minutes from Rockport)
• Portsmouth, NH (30 minutes from Newburyport)
• Kittery, ME (10-15 minutes from Portsmouth)
• York, ME (15 minutes from Kittery)
• Ogunquit, ME (15 mins from York)
• Kennebunkport, ME (30 minutes from Ogunquit)
• Old Orchard Beach, ME (30 minutes from Kennebunkport)
• Cape Elizabeth/Portland Head Lighthouse (30-40 minutes from Old Orchard Beach)
• Portland City Center/Old Port (15-20 minutes from Cape Elizabeth/lighthouses)

Best Things To See When Driving From Boston To Portland, Maine

Okay, so now that you know the general route, here’s a detailed breakdown of all the towns you’ll pass through, why they’re worth stopping in, and the best things to do in each one.

1. Salem, MA

Salem is known for its history with the Salem Witch Trials, an of course, all things Halloween, but it’s honestly a really great little place to explore year-round. There’s a lot more to discover besides all the witch history (although, that’s also very fun and interesting).

If passing through while driving Boston to Portland, Maine, I suggest seeing these things in Salem:

• Visit the Salem Witch Memorial.
• Lunch at the Lobster Shanty (go for the lobster martini!).
• Get a grounds ticket to explore The House of Seven Gables (meander through the nearby side streets in the neighborhood for cool historic homes, too).
• Walk by the Witch House (especially if you visit in the fall).

Psst! I have some helpful guides including planning the perfect Salem, MA day trip , and the best time to visit Salem if you need more information 😉

2. Optional Stop: Rockport, MA

I labeled Rockport as optional because to get there, you’ll have to veer a bit off-course from your drive to Portland. But, I think it’s worth it if you have the time, and have never been before. This detour will add just over an hour of driving time (plus any time you spend in Rockport).

Rockport is one of the most unique towns in New England, and because it sits right along the water, it’s incredibly scenic. If you’re a fan of the movie The Proposal , you may also recognize some of the filming locations in Rockport! A few other movies have been filmed here, too.

If passing through while driving Boston to Portland, Maine, I suggest seeing these things in Rockport:

• Explore the unique shops and art galleries along Bearskin Neck
• Head over to Motif 1, the most painted building in the country (just off Bearskin Neck).
• Grab an ice cream from The Ice Cream Store, the cutest little New England ice cream shack.
• Walk down to the end of Bearskin Neck to cross the breakwater jetty.
• If you’re in need of lunch during your visit, Roy Moore Lobster Co. has an awesome lobster roll.

Click here to read my guide on all the best things to do in Rockport!

Bonus Suggestion: Drive The Whole Massachusetts North Shore

If you have extra time, you could take your time getting out of Massachusetts, and spend the day driving along the entire North Shore region. I highly suggest this because this is a really beautiful area, and you’ll see some amazing coastal New England towns , but I would only do this if you’re able to spend at least 3 days for the entire road trip, as this will take up an entire day.

Two of the main towns along the North Shore, Salem and Rockport, are suggested above. But if you’re able to add on this part of the drive, you’ll want to explore these towns in this order, starting in Boston:

• Manchester By The Sea

I have some posts all about this region of Massachusetts to help you get some ideas on what to do in these towns:

Click here to read about the best things to do in Cape Ann (a part of the North Shore)!

Click here to read about the best things to do in Marblehead!

3. Newburyport, MA

Newburyport is a really beautiful and picturesque town along the northern coast of Massachusetts that I feel is very underrated. If you make this stop while driving Boston to Portland, Maine, you don’t need to spend a lot of time here, but getting out in Newburyport to stretch your legs, explore the charming Market Square and waterfront park is absolutely worth it.

Here’s what I suggest seeing when stopping in Newburyport for a few hours:

• Explore the charming brick-lined streets of downtown, and visit the cute shops.
• Walk along the waterfront path to admire the views.
• If you’d rather visit something more outdoorsy, head to Plum Island and walk on the shoreline of Plum Island Beach.
• On Plum Island, you can also visit the Parker River National Wildlife Refuge , and I recommend the Hellcat Boardwalk Trail (which is very easy, scenic and relaxing, and not as scary as it sounds).
• Pop into Plum Island Soap Co.

Click here to read my full guide to visiting Newburyport!

4. Portsmouth, NH

Portsmouth is one of my favorite towns in New Hampshire, and one of the best coastal destinations in the state. This is another great little area that you can easily see in just a few hours, and is also the perfect place to grab a bite to eat, or pick up a snack for your drive from Boston to Portland.

In Portsmouth, you’ll find lots of charming streets, a great little downtown with truly awesome shops, a wonderful bakery (which I’ll list below), and really incredible restaurants.

Here’s what I suggest seeing when stopping in Portsmouth when driving Boston to Portland, Maine:

• Get some treats from Elephantine Bakery (they also do online ordering if you’re short on time!). I especially love their croissants and s’mores brownies.
• Walk through downtown to visit the shops ( Sault New England and Jane Gee are two really nice ones).
• Swing by Portsmouth Brewery for a glass of beer.

Click here to read all about the best New England gifts and things you can buy! Many of them can be purchased on this drive.

5. Kittery, ME

Kittery is a fun, quick stop to make, but it’s also one of the ones I would suggest you skip if you’re short on time. Kittery has a couple of scenic areas that make for a nice moment to get our of the car, stretch your legs and snap a photo, but I think most of the other stops mentioned on this list are more worth your time.

I’m definitely not saying that Kittery isn’t worth a stop because it definitely is (or it wouldn’t be on this list!), but if you’re looking to cut out a few stops, I think places like Ogunquit, Portsmouth, Rockport, etc. will provide more fun in exchange for your time. Hopefully that makes sense!

That said, there are some really cool things to visit in Kittery, and here’s my list of places to check out:

• See the Badger Island buoy shack.
• Grab a lobster roll at Bob’s Clam Hut.
• Visit the famous When Pigs Fly Company Store .
• Do a little shopping at the outlets.

6. York, ME & Cape Neddick

York and Cape Neddick are great areas to stop in when driving Boston to Portland, Maine, and offer a nice mix between walking around town to do some shopping and dining, or getting out into nature. In this area, you’ll have options from hiking mountains, visiting beaches, exploring the shops, grabbing a bite to eat and seeing one of the best lighthouses in Maine.

Here’s my list of things to check out in York and Cape Neddick during your drive:

• Visit the Stonewall Kitchen flagship store.
• Hike the Mount Agamenticus trail for spectacular mountain views (especially amazing in the fall!).
• Walk along one of the beaches in York (Long Sands Beach is my personal favorite).
• Take in the views at the Bald Head Cliff.
• Visit Cape Neddick to see Nubble Lighthouse.

Looking to do on a lighthouse road trip through Maine? Click here to read about my itinerary for the best Maine lighthouse driving tour!

7. Ogunquit, ME

Ogunquit is such a fun little coastal town in southern Maine, and it’s one of the destinations I recommend the most if you’re looking for a great mix of beach time and small town charm. I also think it’s one of the best beach towns in New England . It has such a fun downtown area with great shops and restaurants, and the beach in Ogunquit is really stunning.

This is an awesome destination to stop in when driving Boston to Portland, Maine, especially if you’re hoping to hear the sound of the craving waves.

Here’s what I suggest you do in Ogunquit when stopping during your road trip:

• Walk Marginal Way from town in Ogunquit, which ends in Perkins Cove, a small little village in Ogunquit. This pedestrian path along the coastline just over a mile each way, so plan your time accordingly. If you do one thing during your time in Ogunquit, I would say this is it.
• Explore the shops in town (Goods Ogunquit is especially fun to visit).
• Walk along the shores of Ogunquit Beach, which has 3 miles of pristine sand.
• Grab a lobster roll at the Lobster House (right by the beach), and hopefully you can get a table outside.

Click here to read more about the best things to do in Ogunquit!

8. Kennebunkport, ME

I can never decide if I prefer Ogunquit or Kennebunkport, but what I can tell you is, they’re both definitely worth visiting when driving Boston to Portland, Maine. Kennebunkport is a charming little coastal town in southern Maine that has some great shops, amazing restaurants, awesome things to see and some nice beaches to explore. It definitely has its own vibe that is really fun to experience.

Here’s what I suggest you do in Kennebunkport when stopping during your road trip:

• Walk around Dock Square to visit the shops.
• Grab some seafood at the Clam Shack or a lobster roll and chowder at Allison’s .
• Get a drink at Batson River Brewing & Distillery (this is one of my favorite places in New England for a cocktail!).
• Take a drive to Cape Porpoise for nice views of the water (visit the Farm + Table store while there for unique and fun home decor, candles, etc).
• Visit one of the beaches (Gooch’s and Mother’s beaches are my favorites in Kennebunkport).

9. Old Orchard Beach, ME

One of the most iconic sites in southern Maine is the pier at Old Orchard Beach, and this is a cool place to stop when driving from Boston to Portland, Maine because you’ll kind of feel like you’ve stepped back in time.

When I visited, I almost felt as if I was transported to an old-timey state fair, in a good way, of course. You’ll find an old-fashioned pier with vendors selling fried dough, drinks and other street foods. Close to the beach, you’ll find a small amusement park and mini golf places, too.

Here’s what I suggest you do in Old Orchard when stopping during your road trip:

• The best thing to see is Old Orchard Pier right at the beach. Definitely walk around the actual pier, and plan to get a few fun fair foods, for sure! Also, walk along the beach to see it from a distance, and walk under it for some cool photo opportunities.
• If you’re feeling like taking some amusement park few rides, head over to Palace Playland.
• Feel like a kid again at Pirate’s Cove Adventure Mini Golf.

Tip : Expect to pay for parking while visiting Old Orchard, and the closer to the beach you are, the more it will be. On average, parking costs about $20 for the day (many lots didn’t offer by-the-hour parking when I visited). So, if you only want to see the pier and don’t want to pay to park for the whole day, this may be a good stop to skip.

10. Cape Elizabeth, ME

Cape Elizabeth is a town that’s actually part of Portland, but it’s south of the main city, and you’ll get to this part before driving into downtown Portland.

This is where the 3 Portland lighthouses are, and I highly suggest planning time to see all of them. They’re actually very close to one another, which makes it easy to see them all within a couple of hours at most. You can either visit them all before getting into Portland, or depending on your schedule, plan to take a quick drive out to see them during your stay in Portland (if you’re staying overnight).

Since you’re driving from the south, I suggest making these stops in this order in Cape Elizabeth:

• Portland Head Light. This is one of the most iconic sites in Maine, and also the most popular New England lighthouse . You’ll find amazing views here, and if you can only see one lighthouse, this is the one to see.
• If arriving in the morning, I highly recommend stopping at Scratch Bakery before visiting the other two lighthouses. They have awesome bagels, and really delicious baked goods. They also do online ordering, so you can order ahead and pick-up when you arrive to save time.
• If you have time, head over to Willard Beach next. This is a small beach, but what makes it worth the stop is the cute little beach cottages all the way to your right. Walk across the beach to get to them, enjoy the views from there. If you happen to arrive at high tide, you’ll need to access the beach cottages via Deake Street, though.
• Spring Point Ledge Lighthouse is next, and this is a fun one because you can walk across the entire breakwater and get right up to the cute little lighthouse.
• Bug Light is last, and is located in a small, but really nice, little park. This is one of the most unique lighthouses in New England, as it’s very ornate in its design. It also makes for fun photos.
• After these stops, you can drive off to downtown Portland!

Editor’s Note : The beach shacks overlooking Willard Beach were destroyed by a storm in January 2024, and are no longer there. However, the community already has plans to rebuild them. I’m closely monitoring this, and will update as soon as I have more information, but it will likely take at least a year, but likely longer. I wanted to keep this suggestion in place, since the views from this spot are still nice, even without the cottages.

Things To Do Once You Arrive In Portland, Maine

Portland is a cool city to explore, and is packed with history, charming streets and tons and tons of amazing restaurants (this is actually one of the best cities in the Northeast for foodies!). Here are some highlights to check out once you arrive in Portland:

• Old Port district.
• Tour the breweries.
• Walk along the Eastern Promenade.
• Take the ferry to Peaks Island.
• Explore the Portland Observatory.
• Obviously, eat all the delicious food. Click here for an awesome food tour of Portland!

Click here to read all about the best day trips to take from Portland, Maine!

Want to keep driving up the coast of Maine? Click here to read about the best stops to make when driving from Portland to Acadia National Park!

Best Places To Stay During The Drive

If you have time to break up your drive and really enjoy all these fun places to visit, these are the towns I would recommend you stay the night in based on options for things to do, and great restaurants:

Rockport is a really awesome place to spend the night because it has a really cool little shopping district, wonderful restaurants and is overall, a really unique destination. My favorite place to stay is the Addison Choate hotel, which is only a 10-minute walk to Bearskin Neck, and offers really beautiful rooms to stay in.

Click here to book your stay at the Addison Choate in Rockport!

If you’re looking for a luxury stay while driving Boston to Portland, Maine, Cliff House in Cape Neddick is the perfect place for you. It’s just about half-way between Boston and Portland, and has all the amazing, luxury amenities you’d expect like gorgeously appointed rooms with ocean views, incredible on-site restaurants, a spa and every square inch of their property offering dramatic coastline views.

Click here to book your stay at Cliff House in Cape Neddick!

Ogunquit is one of my favorite coastal towns in Maine, and makes for a great stop to stay the night or two. There are lots of shops and restaurants to choose from, as well as Ogunquit Beach to enjoy. If you’re looking for a nice place to stay by the beach, I really love Terrace By The Sea , which provides ocean views from their front porch (where you can sit and enjoy a glass of wine at sunset!), and is a very short walk to town, or to the ocean.

Click here to book your stay at the Terrace By The Sea in Ogunquit!

Kennebunkport is another of my favorite towns for an overnight stay, and one of the best places to book a room is the Cottages at Cabot Cove . This hotel is a grouping of individual cottages that are uniquely decorated, and you’ll get to pick which one you want to stay in when you make your reservation. Each morning, a cooler with breakfast goodies is hung on your door, and you also can use the hotel’s canoes to explore the cove. I have a hard time not staying here when I visit Kennebunkport.

Click here to book your stay at the Cottages at Cabot Cove in Kennebunkport!

What Is Halfway Between Boston and Portland, Maine?

As mentioned above, York and Cape Neddick are about halfway between Boston and Portland, Maine. Portsmouth, NH and Kittery are also about halfway between the two cities.

Can You Take A Day Trip To Portland, Maine From Boston?

You sure can! The drive will likely average about 2 hours one-way on a weekend without any stops, and if you carefully choose and plan which stops you want to make on your way to and from Portland, and are strategic with your time, you can definitely do it as a day trip. You could also just drive straight to Portland and spend all your time there.

Best Day Trip Itinerary For Boston To Portland, Maine

For a Boston to Portland, Maine day trip, I suggest trying to take this day trip in the summer when the days are longer, which will afford you more time to see as much as possible. But really, spring and fall are also a great time to take this trip (especially early spring when the days are also longer). Winter is the only time of year a day trip from Boston to Portland, Maine might be tough, since the days are so short.

Suggested Itinerary For A Day Trip From Boston:

Morning : Begin early, and drive to Ogunquit (about 1 hour and 20 minutes from Boston, depending on traffic). I suggest Ogunquit because chances are, if you live or are coming from Boston, you’ve already experienced nearby places like Salem and Newburyport. Ogunquit is further away, and likely not a place you’ve visited as often (or at all).

Late Morning : Leave Ogunquit and drive to Cape Elizabeth to see Portland’s lighthouses (Portland Head Light, Bug Light and Spring Point Ledge Light). If you only have time for one lighthouse, Portland Head Light is the one to see.

Afternoon : Drive into Portland, park your car for the day, and grab lunch. Spend the rest of your afternoon exploring Old Port, and if you have time, take the ferry to Peaks Island (best in the summer when days are longest).

Early Evening: Decide if you want to stay in Portland for dinner, or drive to Kennebunkport to explore that town for a bit, and grab dinner. If you stay in Portland, I would also suggest doing a beer tasting at one of Portland’s breweries, and maybe walking the Eastern Promenade around sunset. If you decide to head to Kennebunkport, the drive is only about 30-40 minutes from Portland.

Evening : Make your way back to Boston.

Best Time Of Year To Drive From Boston To Portland, Maine

Late spring and early-mid summer (so, June, July and August) are the best times to drive from Boston to Portland, Maine, simply because the weather is typically the nicest, and the days are the longest. Summer in Maine , especially along the coast, is just like anywhere in New England by the water – it comes alive. All the seafood shacks and ice cream places are open, and there’s a lively buzz in the air.

Fall is also a great time to take this drive because of the foliage and the pleasant weather. Just keep in mind that Maine tends to be a very seasonal state, as in many seafood shacks, as well as some restaurants and shops, will begin to close after Labor Day (most stay open through Columbus Day weekend, and some stay open year-round). But I’ve done this drive in early spring, summer and late fall and loved it just as much each time.

Boston in the fall is also lovely, so for a fall trip, it’s a great starting point.

Is There A Train From Boston To Portland, Maine?

Yes, the Amtrak Downeaster train provides service between Boston and Portland, Maine. The train ride typically takes about 2 hours and 30 minutes.

Is There A Bus From Boston To Portland, Maine?

Yes, the Greyhound Bus offers service between Boston and Portland, Maine. The bus ride takes about 2 hours and 30 minutes, and drops you off at the Park And Ride at Marginal Way in downtown Portland. From there, you can walk or Uber to your hotel or your next stop.

More of my road trips you may enjoy:

• My Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary
• 7 Day New England Road Trip Itinerary
• My PERFECT New England Fall Road Trip Itinerary
• Best Stops To Make Driving Boston To Stowe, VT
• Driving Boston To New York City: Best Stops & Routes To Take

You may also enjoy reading:

• Incredible New England Resorts & Spas
• Best Boston Hotels Near The Aquarium
• Best Day Trips In New England
• Things To Do In New England For Your Bucket List
• The Best Acadia National Park Itinerary
• Best Boston Food Tours
• Best Breweries In Portland, Maine
• Summer In New England: Places To Go & Things To Do!
• Fun Places For Blueberry Picking In Maine
• Maine In October: Best Towns For Foliage & Things To Do!
• Maine In November: What To Expect & Things To Do

That’s A Wrap On Driving From Boston To Portland, Maine

Now that you know how to plan the perfect road trip driving Boston to Portland, Maine, I hope you’ve begun to plan your own adventure! This is a great route to get acquainted with some of the best of coastal New England, and since it’s such an easy drive from Boston, it’s perfect for tailoring to your own schedule. Happy driving!

You might also enjoy

Subscribe To My Newsletter

• Privacy Policy
• Terms & Conditions
• Disclosure Policy

Boston to Portland, Maine: The Ultimate Guide to Road Trip Routes and Scenic Stops (2024)

The route from Boston, Massachusetts to Portland, Maine is not a long one- but there are a lot of great places to stop along the way, so it makes a great East Coast road trip. Of course, you can also drive this scenic route in reverse!

Boston is a vibrant city that offers a perfect blend of history, culture, and family-friendly attractions. Families can explore the Freedom Trail, where they’ll encounter iconic sites like the Paul Revere House and the Old North Church as well as world-class museums.

In Portland, Maine, families can immerse themselves in the charming coastal atmosphere. They can visit the Portland Head Light, one of the oldest lighthouses in the country, and explore the Old Port district with its quaint shops and delicious seafood restaurants.

We love road trips- we’ve done a long cross-country route , explored the American Northwest by car, and even driven down into Baja . Although we lived in Boston for many years, we haven’t driven this stretch in a while, so reached out to Laura Mendenhall, a passionate traveler from O Family, Where Art Thou? , to share her experience on this road trip from Boston to Portland, Maine.

Laura spent an incredible three months exploring charming cities along the east coast with her family of 5 in an RV. In this post, they’ll share a bit about their journey from Boston to Portland, Maine including the best routes from Boston to Portland by car, bus, and train, as well as some family-friendly places to stop along the way, and fun things to do while you are there.

This article may contain affiliate links, which means we may earn a small commission if a reader clicks through and makes a purchase.   As an Amazon Associate, we earn from qualifying purchases at no additional cost to you. All our recommendations are our own and are in no way influenced by any advertiser or commercial initiative.

At the bottom of this post,  download a free License Plate Road Trip Game   to play on your next drive!

Lodging: Booking.com Flight Deals: Skyscanner Rental Cars: Discover Cars Airport Transfers: Welcome Pickups

Digital SIM Cards: Airalo eSIM Travel Insurance: SafetyWing

Table of Contents

How far is Boston from Portland, Maine?

Did you know that Boston, Massachusetts is just a short 2-hour drive away from the beautiful city of Portland, Maine? The distance separating these two cities is approximately 109 miles. Whether you opt for a car, bus, or train, embarking on this road trip is truly worthwhile!

Picture yourself cruising along the scenic Interstate 95 North, soaking in the stunning New England landscapes and passing through charming towns. Trust me, the journey is as enjoyable as the destination. So hop in your car, roll down the windows, and let’s embark on this adventure together.

Boston to Portland, Maine: Best Road Trip Routes

You can get from Boston to Portland via car, bus, or even train! Here are the best routes between Boston and Portland, what you’ll see, and even how much they cost.

Are you ready for a road trip? Make sure you have all the road trip supplies , healthy road trip snacks , and car-friendly activities for the kids . Newbie? Not to worry! We’ve got road trip tips for beginners .

Boston to Portland Maine By Car

Direct route: i-95.

The I-95 route from Boston to Portland, Maine is the most direct and popular choice, covering around 110 miles of scenic landscapes. As you travel north, you’ll pass through charming towns, picturesque countryside, and eventually cross the border into Maine.

Make sure to take a break in Portsmouth, New Hampshire, known for its historic appeal. Once in Portland, you’ll discover a lively food scene and a captivating waterfront, making the I-95 route an efficient and enjoyable way to reach your destination.

The Scenic Drive: US-1

If you’re looking for a leisurely and scenic drive from Boston to Portland, Maine, the US-1 route is your perfect choice!

This picturesque coastal road stretches for about 111 miles, taking you through charming seaside towns, breathtaking ocean views, and iconic New England landscapes. Prepare to be captivated by the quaint coastal villages, lighthouses dotting the shoreline, and delicious seafood restaurants along the way.

As you wind your way through this scenic route, you’ll have plenty of opportunities to make memorable stops and explore the beauty of the New England coast. So buckle up, roll down the windows, and get ready for a delightful adventure along the enchanting US-1 from Boston to Portland!

Top Pick: Rent a Car from Discover Cars Discover Cars is our go-to resource for renting cars for road trips. Their pricing is easy to understand, and there are no last-minute surprises. Book Now

Boston to portland maine by bus.

Don’t feel like driving? Taking a bus is another great option and way cheaper than I had expected! To take a bus from Boston to Portland, Maine, you have several options available. Here are some details to help you plan your trip.

Buses traveling from Boston to Portland, Maine typically follow a direct route without scheduled pit stops for town tours. However, there may be brief rest stops along the way for passengers to stretch their legs and use restroom facilities. If you want to explore specific towns, it’s advisable to consider alternative transportation or plan separate trips to those destinations.

How Much Does a Bus from Boston to Portland, Maine Cost?

Approximate ticket prices range from $15 to $35 for a one-way route. The cost of taking a bus from Boston to Portland, Maine varies depending on the bus company, time of travel, and whether you book in advance. It’s recommended to check the respective bus company websites for the most accurate and up-to-date fares, and booking in advance can often secure better prices and availability.

Greyhound offers multiple daily departures from Boston to Portland. Buses typically depart from Boston’s South Station and arrive at Portland’s Transportation Center. The journey takes approximately 2.5 to 3 hours, depending on traffic and specific route variations. Check the Greyhound website for the most up-to-date schedules and ticket prices.

Concord Coach Lines

Concord Coach Lines also operates regular bus services between Boston and Portland. Buses usually depart from Boston’s South Station and arrive at Portland’s Transportation Center. The travel time is similar to Greyhound, around 2.5 to 3 hours. It’s advisable to Visit the Concord Coach Lines website for the latest schedules and ticket information. 

Megabus is another option for traveling from Boston to Portland. They provide daily departures from Boston’s South Station, and the buses arrive at Portland’s Transportation Center. The duration of the trip is comparable to Greyhound and Concord Coach Lines, around 2.5 to 3 hours. Check the Megabus website for the most accurate and up-to-date schedules and fares.

When planning your trip, consider factors such as departure times, ticket prices, and seat availability. It’s generally advisable to book your tickets in advance to secure your preferred departure time and to ensure availability, especially during peak travel periods.

Boston to Portland Maine by Train

Experience the convenience and charm of traveling by train from Boston to Portland, Maine! You will be taking the Amtrak Downeaster and the route would cover approximately 115 miles and offers a comfortable and hassle-free way to explore the beauty of New England.

Amtrak Downeaster Train

The Amtrak Downeaster train provides service between Boston’s North Station and Portland Transportation Center. The ticket prices for this route typically range from $20 to $60 , depending on factors such as the type of ticket and advance booking.

The travel time is approximately 2.5 to 3 hours , offering a comfortable and scenic journey through New England.

It’s advisable to check the Amtrak website for the most accurate and up-to-date schedules and fares and to book your ticket in advance to secure your preferred departure time and ticket type.

Best Road Trip Stop Between Boston and Portland

Whichever route you choose to drive from Boston to Portland, Maine, here are some great scenic stops and coastal towns to see along the way.

Don’t miss our top tips for enjoying a road trip with kids , as well as our best travel tips for kids no matter where you are headed!

The Scenic Route: Boston to Portland via US-1

If you are taking the scenic drive along I-10 from Boston to Portland, here are the must-see scenic stops. These unique and beautiful pit stops along the US-1 route offer a mix of history, natural beauty, and coastal charm, adding a touch of magic to your road trip from Boston to Portland, Maine.

Salem, Massachusetts

Begin your journey with a stop in the historic town of Salem, known for its witch trials. Explore the Salem Witch Museum , stroll through the picturesque streets lined with charming colonial architecture, and immerse yourself in the town’s fascinating history.

Salem is a great place to spend some time- there’s fascinating history here that you won’t find elsewhere in the US. Consider adding a history of Salem walking tour to your road trip itinerary:

Hauntings of Salem Walking Tour

This historical walking tour gets over 5,000 five-star reviews! That’s incredible. Start at the old Town Hall in Salem and learn about 400 years of Salem history from a local historian.

You’ll learn about the Witch Trials Hysteria of 1692, how Salem became a prominent seaport, and stories of some of the families that rose to wealth along the way. You’ll visit the controversial Bewitched Statue of Elizabeth Montgomery, and then end at the Salem Witch Trials Memorial.

“Jeremiah was an amazing guide! He did a wonderful job drawing everyone, of every age, not only into the wicked history of the witch trials, but also shared many other fascinating facts about Salem.” -Katherine p (read more reviews )

This tour is great for all ages, even dogs are welcome! During peak season (October, of course) there may be up to 40 people on this tour. You can choose a daytime tour, or go for a spookier, lantern-led evening tour! Tours run rain or shine. The evening tours book up fast- tours depart as early as 9 am, and as late as 9 pm.

Book Now: Hauntings of Salem Walking Tour

Rockport, Massachusetts

Discover the picturesque coastal village of Rockport, famous for its iconic Motif No. 1 fishing shack and scenic harbor views. Enjoy browsing the art galleries, exploring the quaint shops, and indulging in delicious seafood at one of the waterfront restaurants.

Camden, Maine

Experience the beauty of coastal Maine in the charming town of Camden. Admire the stunning views from the top of Mount Battie, stroll along the scenic harbor, and visit the historic Camden Opera House for a dose of culture.

Windjammer Classic Sunset Sail

Need some time on the water? Pause in this Camden, and take a sunset sail on a classic windjammer. This two-hour boat trip takes you along the Maine coastline, with wonderful sunset views. You’ll sail past Curtis Island Light and into Penobscot Bay. You can help hoist sails, and even take a turn at the wheel of this traditional wooden ship. Departure times vary with sunset.

“The Captain and crew made this the best sail we’ve ever taken! Perfect 2 hour family sail and the Captain told the entire history of the ship and why these are so important to our history.” -Amy_V (read more reviews )

Book Now: Windjammer Classic Sunset Sail

Pemaquid Point, Maine

Make a stop at Pemaquid Point to see its iconic lighthouse perched on rugged cliffs overlooking the Atlantic Ocean. Explore the surrounding rocky shores, visit the Fisherman’s Museum, and capture breathtaking photos of the dramatic coastal scenery.

Boothbay Harbor, Maine

Immerse yourself in the quintessential coastal charm of Boothbay Harbor. Take a scenic boat tour to explore the nearby islands, visit the beautiful Coastal Maine Botanical Gardens, and savor fresh seafood at one of the waterfront restaurants.

The Direct Route: Boston to Portland via I-10

If you are taking the direct route (I-10), from Boston to Portland, here are the must-see pit stops. These pit stops offer a mix of natural beauty, cultural attractions, and coastal charm, making your road trip from Boston to Portland, Maine, even more memorable.

Portsmouth, New Hampshire:

Explore the charming waterfront city with its historic architecture, bustling marketplaces, and picturesque coastal views. Don’t miss a visit to Strawbery Banke Museum , where you can step back in time and experience life in early America.

This is a great place to stop and do an Islands and Harbor Portsmouth Bike Tour !

Kids 10 and up can participate in this tour. During this 2-hour bike tour , you’ll ride across the Piscataqua River and head to the outer islands of Portsmouth, learning stories about the area as you go, including about “Live Free or Die” Captain John Stark.

“A fun adventure filled with history, moderate exercise, and lovely views. We had time to enjoy a break at each stop while we learned about each location.” -victoria (read more reviews )

Book Now: Bike Tour of Portsmouth Harbor and Islands

Kennebunkport, Maine

Discover the coastal beauty of this quaint town known for its stunning beaches, charming shops, and delightful seafood. Visit the iconic Cape Porpoise Pier, take a scenic boat tour, or indulge in a delicious lobster roll.

Family Detour: You can do a fun scavenger hunt in Kennebunkport- this hunt takes about two hours, and will have you exploring the town both inside and outside. You’ll have challenges, solve clues, and interact with a live (but remote) host. Players give it five stars!

Book Now: Family Scavenger Hunt in Kennebunkport

Ogunquit, Maine

Experience the natural beauty of Ogunquit with its pristine sandy beaches, rugged cliffs, and scenic coastal walks. Take a stroll along the Marginal Way, a picturesque footpath that offers breathtaking views of the ocean.

Portland Head Light, Cape Elizabeth

Make a stop at this historic lighthouse, one of the most photographed in the United States. Enjoy panoramic views of the rugged coastline and capture memorable photos of the iconic red-and-white striped tower.

Freeport, Maine

Shopaholics will love a visit to Freeport, home to the famous L.L.Bean flagship store and numerous outlet shops. Explore the charming downtown area, dine at delicious seafood restaurants, and enjoy the vibrant atmosphere.

Best Stops from Boston to Portland via the Train

These fun and interesting pit stops along the train route from Boston to Portland offer a diverse range of experiences, from beachside fun to cultural attractions and scenic beauty, ensuring an exciting and memorable journey.

Old Orchard Beach, Maine

Get off at the Old Orchard Beach station and spend some time exploring this vibrant beach town. Enjoy the sandy shoreline, take a stroll on the iconic pier, and indulge in classic seaside treats like ice cream and fried dough.

Hop off at the Freeport station and discover the famous L.L.Bean flagship store , where you can shop for outdoor gear and clothing. Explore the charming downtown area, browse through unique shops and boutiques, and sample local cuisine at one of the cozy restaurants.

Brunswick, Maine

Take a break at Brunswick and visit Bowdoin College , a prestigious liberal arts college known for its beautiful campus and cultural offerings. Explore the college grounds, visit the Bowdoin College Museum of Art , and take a leisurely walk through the quaint downtown area.

Portland Head Light, Maine

Arrive in Portland and make your way to the iconic Portland Head Light, one of the oldest lighthouses in the United States. Enjoy stunning views of the rugged coastline, learn about the history of the lighthouse, and capture memorable photos of the picturesque surroundings.

Old Port, Portland, Maine

Step off the train and venture into the charming Old Port district of Portland. Explore the cobblestone streets lined with boutique shops, art galleries, and waterfront restaurants. Take a scenic harbor cruise, sample fresh seafood, and soak in the lively atmosphere of this historic old port area.

Visiting Boston: Top Things to Do with Kids

There are so many things to do in Boston for all ages, here are just a few of the things that we enjoyed in our time there, that we highly recommend for families. These unique attractions in Boston offer memorable experiences that are sure to captivate the imaginations of children.

Whether it’s participating in a historical reenactment, learning about the American Revolution, exploring the city by land and water, or encountering fascinating wildlife, there’s something for every young adventurer in Boston.

Boston CityPASS

If you’ll be spending a few days in Boston, consider getting a CityPass – it’s good for 9 consecutive days from when you first use it. It includes admission to the New England Aquarium (one of our favorite places in Boston!) and the Museum of Science, Boston (also amazing), plus two other attractions of your choice, including a Boston Harbor Cruise.

Book Now: Boston CityPASS

Boston Tea Party Ships & Museum

Step back in time and relive the iconic Boston Tea Party at the Boston Tea Party Ships & Museum . Kids can participate in a reenactment, throw “tea” into the harbor, and explore interactive exhibits to learn about this pivotal event in American history.

Freedom Trail

Discover the thrill of exploring the renowned Freedom Trail with your family. This 2.5-mile historic route showcases 16 significant sites which immerse your children in American history. The trail starts at Boston Commons, the oldest public park in the country, and includes Paul Revere’s House, and the USS Constitution Museum among others.

You’ll get the most out of the Freedom Trail with this five-star small group tour . No more dragging your kids over to read placards! This tour starts at Boston Commons, lasts 2 1/2 hours, and ends at Copps Hill.

“Ted was an amazing tour guide and historian. He brought the story to life and told it how it really happened not what we want to believe happened.” William_S (read more reviews )

Book Now: Small Group Freedom Trail Walking Tour

Boston Duck Tours

Hop aboard a colorful renovated World War II amphibious vehicle and embark on a Boston Duck Tour , a unique way to see the city. Kids will love the exciting ride that takes them through the streets of Boston and then into the water for a scenic cruise along the Charles River. The big “splash” into the water is always a favorite moment!

Duck tours last 1 1/2 hours, and cover most of the major sites in downtown Boston from Boston Commons to Newbury Street, to the Prudential Center. This is a great way to get an overview of the city if it’s your first time visiting Boston.

“t was really cool hearing the back story to a lot of historic buildings, and it’s a great way to start your trip to Boston off. It gave a lot of places and ideas for what to visit in person next! “ Tia_E (read more reviews )

Book Now: Boston Duck Tours

Other things we highly recommend doing in Boston: a tour of Fenway Park , and a walking food tour of the North End (Italian quarter).

Visiting Portland Maine: Top Things to Do with Kids

Portland Maine has a ton of family-friendly activities, here are some of our favorites that we highly recommend to other traveling families. These fun and easy activities in Portland, Maine, provide opportunities for family bonding and exploration.

Whether it’s marveling at a historic lighthouse, engaging in hands-on learning at a children’s museum, or enjoying a scenic ferry ride, Portland and the old port area offers plenty of family-friendly attractions for all to enjoy.

Explore the Portland Head Light

Visit the iconic Portland Head Light, a historic lighthouse perched on the stunning shores of Cape Elizabeth. Take a leisurely stroll along the scenic trails, enjoy a picnic with a view, and let the kids explore the rocky beach for seashells and tide pools.

Portland City and 3 Lighthouse Historical Tour

If you really want to see iconic lighthouses, take this 1.75-hour lighthouse tour that includes the city of Portland, as well as visits to three lighthouses: Portland Head Light, Spring Point Ledge Lighthouse, and Portland Breakwater Lighthouse. You’ll be led by a librarian who knows the city well and will share local lore along the way.

Book Now: Portland City and 3 Lighthouse Historical Tour

Take a Casco Bay Ferry Cruise

Embark on a family-friendly cruise around Casco Bay, where you can enjoy picturesque views of the coast, islands, and lighthouses. Choose from various cruise options, including narrated tours or island-hopping adventures, and make lasting memories as you sail together on the sparkling waters.

Casco Bay Tall Ship Cruise

This windjammer cruise is two hours of cruising on the ocean. Help hoist the sails on this traditional wooden boat, then sit back and watch for wildlife along the shores.

“What an experience and what a gorgeous boat! The cruise led us around the harbor that’s steeped in history. The captain and his crew invited us to participate in raising the sails, how fun, and we saw two seals while cruising, so cute!” -Heather_B (read more reviews )

Book Now: Casco Bay Tall Ship Cruise

The Casco Bay Narrow Gauge

The Main Narrow Gauge is a charming, historic railway that offers scenic rides along the waterfront of Portland, Maine. With its vintage steam and diesel locomotives, the railroad provides a unique experience for families to step back in time and enjoy the picturesque beauty of Casco Bay.

Other things we recommend doing in Portland: Take a one-hour open-air trolley tour of the city, or take a donut-tasting walking tour !

FAQs: Boston to Portland, Maine Road Trip

Boston and Portland, Maine are approximately 109 miles apart, making it a convenient and relatively short distance for a road trip or other modes of transportation between the two cities. The short distance means you have a lot of time to stop and explore the area in between these cities. Keep in mind, once you are in Portland, you are only three hours from the epic Acadia National Park .

The best time for a road trip from Portland, Maine to Boston is during the summer months of June to August, with favorable weather and abundant activities and events to enjoy along the way.

Unfortunately, no, there is not a direct ferry that goes from Boston to Portland, Maine. However, there is The Casco Bay Lines which operates a ferry service between Portland, Maine, and the Casco Bay Islands. 

Yes, you can take a bus from Boston to Portland, Maine. Several bus companies, such as Concord Coach Lines and Greyhound, offer regular bus services between the two cities, providing a convenient and affordable transportation option for travelers.

The halfway point between Boston, Massachusetts, and Portland, Maine is typically around the Wells area. It’s approximately 55-60 miles from both cities and serves as a convenient rest stop for travelers on the route. Wells is known for its beautiful beaches, charming downtown area, and various dining options, making it a great place to take a break during your journey.

There You Have It: Boston to Portland, Maine Road Trip Routes

A road trip from Boston to Portland, Maine is an ideal family vacation, offering a blend of natural beauty, historical sites, and family-friendly attractions. There are countless benefits of traveling as a family . My family and I made lasting memories and look forward to taking this road trip again!

With this road trip itinerary, you can explore picturesque coastal towns, visit charming lighthouses, and indulge in fresh seafood. Kids will love the sandy beaches, scenic hiking trails, and the chance to learn about American history at museums and landmarks.

This travel guide allows for flexibility and discovery, allowing families to create memorable experiences together. From stunning landscapes to engaging activities, a road trip from Boston to Portland offers something for everyone, making it a perfect choice for a summer family getaway.

Traveling along the East Coast? We’ve got lots of family road trip stops , including guides to visiting Washington DC , and a beginner’s guide to New York City .

Cynthia Matthews von Berg is the founder of Sharing the Wander. She is a passionate traveler, mom, and travel coach specializing in long-term travel and family travel. She and her family embarked on a Family Gap Year in 2021, and haven't looked back.

Boston to Maine: 5-Day New England Fall Road Trip Itinerary

This post contains affiliate links which means that I will make a small commission if you purchase a product after clicking on any of them, at no extra cost to you.

Fall is my absolute favorite time of the year! We don’t get to experience much of the lovely fall weather in Tampa , so it always feels like the perfect time to make a trip up north. New England is one of the best (and most popular) places to road trip in the fall!

There are so many activities available during this season! Go leaf peeping in New England or do an apple cider tour in Vermont. This fall road trip will take you from Boston to Portland Maine, making stops along the way that showcase some of these unique cities and towns!

We did our New road trip at the end of October and missed peak foliage. Nonetheless, we were still able to enjoy the colors of nature. Peak foliage varies year to year so use this foliage tracker to help you plan your fall road trip.

Table of Contents

Quick links for your New England road trip

🏨 Accommodation

Easily compare prices, secure great deals, and enjoy the added benefit of flexible cancellations up to 24 hours in advance for the majority of hotels with Booking

🎟️ Tours and tickets

Discover your next adventure with ease by using Viator which allows you to explore a multitude of local tours, ensuring you find the best experiences at the best prices.

🚘 Car rental

Rentalcars is the best tool for comparing prices for your date amongst the most popular rental car companies!

New England fall road trip itinerary

Day 1: drive from boston to maine with a pitstop in salem, massachusetts.

In order to avoid traveling from a different city or state the day our flight left from Boston, we decided it would be best to just head right to Maine and enjoy Boston on our final day. It’s just a short 2-hour drive from Boston to Maine, but first I suggest making a pitstop in Salem which is just 40 minutes outside of the city.

Salem’s historic reputation for witchcraft comes from the Salem witch trials of 1692, in which 20 people were tried and executed. Today, Salem is a tourist destination known for its Halloween celebrations, as well as its many attractions.

The city is also home to a number of historic sites, including the House of the Seven Gables, which was built in 1668. It’s one of New England’s most famous landmarks, and it’s also where Nathaniel Hawthorne set his novel “The House of the Seven Gables.”

We only had a few hours in Salem for our road trip, but fell so in love with this charming, spooky city! This may have been one of my favorite stops on our New England fall road trip.

Things to do in Salem, Massachusetts

• Take some pics at the Hocus Pocus filming locations . I mean it is a classic ! Most of the locations are pretty easy to get to, so I’d try to squeeze in a couple while you’re here. Here’s a list of where you can find all the spots.
• Visit The Witch House (The Jonathon Corwin House). It was home to Judge Jonathan Corwin (1640–1718) and is the only structure still standing in Salem with direct ties to the Salem witch trials of 1692. It’s open 7 days/week from 10 AM – 5 PM. Meaning if you have a mid-afternoon flight, this may be the first thing you want to do. Admission is $9 for adults.

• Check out the fun shops— just strolling around the downtown area is beyond pleasant. They have some super neat shops, including plenty of places to get a reading (you know I couldn’t resist!).
• Grab a bite and drink at The Roof . You’ll love this rooftop bar. We were even lucky enough to enjoy it under an eerie full moon! They have tacos, burritos, and bowls served alongside fun cocktails and shooters (or beer if you wish).
• We didn’t have the time, but if all of this hocus-pocus stuff intrigues you and you have some time to spare you can check out the Salem Witch Museum to learn more (adult admission is $16.50, and it’s open daily from 10 AM – 5 or 7 PM depending on the time of year). There are also some really interesting walking tours like the Voodoo, Vampires, and Ghosts Walking Tour or the Salem Night Walking Tour .

Once you’re done enjoying your time in Salem, head to your hotel in Portland. It’s just a little over an hour’s drive! We stayed at the Holiday Inn Portland – By the Bay .

🏨 Book your stay in Portland

With a great location in Portland, and just a short drive from Salem, Holiday Inn Portland By the Bay is the perfect place to stay in Portland!

Day 2: Portland, Maine

I’ve heard plenty of great things about Portland, and it lived up to the hype! I would love to go back to experience it during the summer months.

Portland is a diversified coastline area that welcomes guests with a variety of unique Maine experiences. You have access to it all—shopping, sailing, beaches, amazing restaurants, and more. This metropolis with a small-town feel is a cultural hotspot and a nature lovers’ paradise. It is home to craft breweries, ocean cruises, and a renowned culinary and cultural scene.

For the most part, we just took ourselves on a self-guided foodie tour and enjoyed strolling around this charming coastal city.

Things to do in Portland Maine

• Grab a cup of joe from  Bard Coffee . We were able to walk here from our hotel, and the weather was an absolute dream. The coffee was delicious! The inside wasn’t open at the time due to COVID restrictions, but it worked out because we snagged our coffee and strolled down the cobblestone streets to the next spot.

• Just a hop skip and a jump away from Bard Coffee is The Holy Donut (they have 3 locations, we went to the one on Commercial Street). This beloved local family-owned spot sells potato donuts with unique variations such as pomegranate, honey lavender, blueberry lemon, and several more! (It’s so funny to me that donuts seem to be just as much of a craze in Portland, Oregon as they are in Portland, Maine.)

• Visit Maine’s oldest lighthouse, the Portland Head Light at Fort Williams Park . With more than 90 acres of open space for enjoyment, there are options for picnics, kite flying, arboretum tours, cliffside loop walks, and exploring the rocky coastline. If you come hungry there are four food vendors (including Cousins Maine Lobster) selling lobster rolls, sandwiches, hot dogs, and gelato. The sights here were extraordinary. This ended up being my favorite thing we did in Portland!

• Grab some chowder and a lobster roll from Luke’s Lobster . You’ll love enjoying these Maine classics with stunning waterfront views. If you’re really hungry you can even order a whole steamed lobster!

• Check out some breweries and distilleries. We visited Oxbow Blending & Bottling  which offers a wide variety of draft and bottle beer from Oxbow and other guest breweries, as well as a unique collection of wine and Amaro. Next door is Hardshore Distilling where you can find some of the greatest and smoothest gin! I was shook at how good it was just to sip on, but they also can make you some fun cocktails with it if you’re not a sipper.
• Grab some frites from Duckfat which is conveniently located right outside of Oxbow Blending & Bottling. They offer a small menu that includes Belgian-style Frites that are hand-punched and twice-fried in duck fat.

Day 3: New Hampshire | Conway, Lincoln, and White Mountain National Forest

The drive from Portland to the White Mountain Forest is just a little over 2 hours. Driving through New Hampshire was an adventure on its own, we were in awe at the colors! Anything that piqued our interest we would just pull off and enjoy.

Because we had such limited time on this trip we did try to cram in as much as we could, however, I know this is only a glimpse into the many amazing fall activities to do in New Hampshire.

Things to do in New Hampshire

• Drive the Kancamagus Highway , a 34.5-mile road trip through New Hampshire’s White Mountain Forest ! The views are stunning; it’s worth taking your time here just to enjoy them. In addition to this scenic road trip route being amazing by itself, there are several points along this route where you can stop off at scenic overlooks with great photo ops.

• Lower Falls is one of the more popular scenic stops along the Kancamagus Highway. There is parking, a picnic area, and restrooms located here. During warmer months people can be found taking a dip in the watering hole.
• Just a few minutes drive separates you from the Albany Covered Bridge . The stream flowing beneath it and fall foilage surrounding it make it another amazing stop on the Kancamagus Highway.

• Eat dinner at The Common Man in Lincoln. We overstuffed ourselves, but it was worth every bite. Their Nantucket pie which includes shrimp, scallops, haddock, and Maine lobster meat baked with lobster cream sauce and seasoned Ritz crumbs gave me life.

We didn’t have time for hikes, but there are so many great ones in the area I definitely hope to have time for our next trip! Here are some popular ones along Kancamagus Highway you may want to check out:

• Diana’s Baths (1.3 miles)
• Flume Gorge (2.2-mile loop)
• Smugglers Notch State Park (several trails to choose from here)

We stayed overnight in Lincoln at the Holiday Inn Express & Suites Lincoln East – White Mountains . Holiday Inn Expresses are usually a little more affordable and always include breakfast which I love. It’s a great way to save a couple of bucks during your New England road trip.

Related read: This southeast USA road trip itinerary , Utah road trip itinerary , and Arizona road trip itinerary are three other great fall road trip options!

Day 4: Vermont | Stowe, Waterbury, and Burlington

Stowe, Waterbury, and Burlington are all great places to visit in Vermont in the fall! Stowe is a little less than 2 hours from Lincoln and has lush forests and rolling hills. A quick 20-minute drive from Stowe gets you to Waterbury which has charm, history, and beautiful valleys.

Just another 30 minutes outside of Waterbury you’ll find yourself on the eastern shoreline of Lake Champlain in Burlington, where Ben & Jerry’s originated.

Things to do in Vermont

• Drive around and admire the beauty of Stowe . Check out the Percy Farm Corn Maze . Don’t be intimidated when they make you exchange phone numbers in case you get lost. It was definitely one of the more challenging corn mazes I’ve ever done, but we made it out in a half an hour!

• Sip on cider slushies and hard cider at Cold Hollow Cider Mill in Waterbury . And of course, you can’t leave without snagging some cider donuts!

• Visit one of Vermont’s cutest gems, Burlington . Church Street Marketplace is an adorable award-winning pedestrian mall home to over 100 shops and restaurants, as well as year-round events, entertainment, and more! We enjoyed lunch at Leunig’s Bistro (the beef bourguignon was phenomenal) and drinks at Foam Brewers , Fiddlehead Brewing Company , and Shelburne Vineyard before heading to our hotel for the night.

Sometimes I reflect on how much we did in one day and it’s kind of wild. We covered three cities and didn’t feel rushed. Makes me second guess complaining there’s not enough time in the day when I can’t get 3 tasks done. We did only get just a taste of them (literally and figuratively), but I feel like what we did and saw were some of the best things to do in Vermont .

We ended up stopping at Molly’s Restaurant in Hanover and staying at Holiday Inn Express & Suites Manchester-Airport . It was 2 1/2 hours away from Burlington and less than an hour away from Boston (where we were heading the following morning).

Day 5: Boston

The final stop on our epic New England fall road trip! Boston is a pretty big city, with plenty to eat, see, and do and flooding with history. I’ve visited twice and don’t even feel like I’ve seen half of what this city has to offer yet! I’ve compiled a few of my favorite things to do in Boston, as well as some things that are still on my list!

Things to do in Boston

• Check out Beacon Hill— This is one of Boston’s most picturesque neighborhoods. The streets are lined with Federal-style and Victorian brick row houses lit by antique lanterns. Acorn Street is located here and it’s one of the most photographed streets in the city. Why you ask? It’s a charming original cobblestone street— something you don’t come across too often nowadays.
• Fenway Park— Go for a game, or just to snap a pic in front of this iconic spot. It’s the oldest of all current major league ballparks!
• Boston Public Library — The Boston Public Library is located in Copley Square, and let me tell ya it’s a stunner. If you’re like me and love a good library, it’s up there for one of the most beautiful and historic I’ve ever been to.

• Do a whale watching tour— If you are visiting Boston during whale watching season (April-October) then a whale watching tour is a must! Enjoy spotting humpback and fin whales, along with Atlantic white-sided dolphins from your high-speed catamaran.
• Freedom Trail — One of Boston’s most iconic things to do! Follow 2.5-mile Freedom Trail that leads to 16 nationally significant historic sites including Paul Revere House (the oldest remaining structure in downtown Boston), Boston Common (America’s oldest public park), Old State House (the oldest surviving public building in Boston), the Old North Church (if you have time, tour the crypt!) and several other historical locations. If you want to get the most out of your experience, they offer affordable guided tours !
• Prudential Center — Enjoy shopping and eating at this gorgeous enclosed shopping center. I especially recommend checking out Eataly! Copley Place is another stunning shopping center located right next door.
• Visit Cambridge— Wander Harvards’ campus, eat and play trivia at The Asgard, or check out one of their fun speakeasies A4cade (located in a grilled cheese shop and full of games) or Brick and Mortar (we actually really struggled to find this one!).

If you want to explore the city in a unique way check out Boston Duck Boat Sightseeing City Tour . You get to tour the city in a renovated World War II amphibious vehicle. The tour begins on the streets and then is taken to the Charles River for a view of the city by boat.

🚌 Hop-On Hop-Off Trolley Tour

If you want a tour that allows you to get off and enjoy some of the stops while also receiving historical info and fun facts check out this 14-stop tour is for you.

Where to eat and drink in Boston

Here are some of my favorite bars and restaurants we got to experience in Boston!

• VERSUS — a super fun arcade bar!

• Citrus and Salt — a Baja-inspired restaurant with Mexican eats and fun, creative cocktails.

• Terra at Eataly—delight yourself with amazing Italian food and craft cocktails in this stunning eatery.

• Legal Sea Foods — best (ok, and only) whole lobster I’ve ever had! It was so unbelievably good, one of the best parts of it is the shrimp & scallop stuffing it was filled with. Also, let’s take a moment to admire all of the lobster in the lobster bisque. They have several locations throughout Boston.

• Trident Booksellers & Cafe —This place is so cozy and especially nice on one of Boston’s dreary days. Come here for good coffee and a good breakfast, and leave with a new book!

We didn’t get to check it out, but the Samual Adams Brewery is located in Boston too!

Are you ready to experience this epic Boston to Maine New England fall road trip?!

If you are looking for a road trip to do in the fall, New England is one of the best. From Boston to Portland, Maine and each stop in between has so much to offer. From beautiful views of rivers, falls, and mountains to great food and fun activities. I hope this post has given you some ideas for your epic fall road trip!

Destiny Snyder is a passionate travel blogger and content creator based in the Tampa Bay area. Originally from a small town near Toledo, Ohio, Destiny's love for exploring new places began when she moved to Florida in 2017. She enjoys uncovering hidden gems, sharing insider tips on the best things to do, places to eat, and coffee shops to visit in every destination. With her blog Guided by Destiny and niche sites Sunkissed in Tampa and Sunkissed in St. Pete, Destiny aims to make trip planning stress-free and fun for her readers.

If I follow this itinerary what states am I staying in what nights ? Thank you .

This was a great and very uncomplicated itinerary compared to so many others! thank you for breaking it down so well. beautiful pictures too!!

Aww thank you so much Tess! That means a lot 🙂

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

Review Cart

No products in the cart.

Your Guide to Wandering

Boston to Portland Maine: The 2023 Trip Guide (By Car or by Train!)

Boston to Portland Maine is one of the best small road trips in the U.S. While the cities are less than two hours apart, you can extend the trip to include many scenic charming towns and coastal views along the way. If you enjoy lighthouses, beaches, and fresh seafood, this is the perfect road trip itinerary for you!

Driving from Boston to Portland

The drive from Boston Massachusetts to Portland Maine itself is pretty straightforward and can take about 2 hours (110 miles) direct on I-95. However, you may want to stretch the journey out to a few more hours or even a few days to see what the New England coastline has to offer. I’d suggest taking a weekend to explore the scenic route, but even an extra few hours can be worth it to take some detours.

Scenic stops on the way from Boston to Portland

If you fancy exploring the coastline or taking a scenic route be sure to incorporate some of these stops into your drive. Leave plenty of time for exploring!

It goes without saying, but be sure to spend a day or two in Boston before you head north. Take a historic walking tour on the Freedom Trail, watch a RedSox game at iconic Fenway Park, or stroll in the park at Boston Public Gardens. The Waterfront also offers scenic views of Boston’s skyline as well as ample opportunities to grab a lobster roll!

You could easily spend 3 days in Boston so be sure to make it a stop on your drive up. Fly directly into Logan International Airport to begin your road trip.

Salem, Massachusetts ~35 minutes from Boston

Salem is the first recommended stop on the road trip due to its historic significance in the Salem Witch Trails. In 1692 25 people were killed for accusations of witchcraft in Salem.

I’d recommend visiting the Salem Witch Trial Memorial as well as the Old Burying Point Cemetary. Stroll down the pedestrian friendly Essex street and stop by the quirky monster and magic-themed shops along the way. This town takes witchcraft seriously .

Be sure to take a Hocus Pocus tour to see some of the houses from the films, as well as a ghost tour to hear about the spirits that still haunt Salem. In October Salem becomes a tourist destination for all things spooky!

Newburyport ~40 minutes from Salem

Newburyport would be a perfect stop for an hour or so to stretch your legs and grab a coffee. It is a quaint town with a beautiful waterfront and cute boutique shops. Check out the Market Square!

If you are interested in exploring the Parker River Natural Wildlife Refuge you could easily spend a full day here. The Wildlife Refuge is on Plum Island and has over 3000 protected acres of salt marsh.

Head straight to the beach, or peruse the biking and walking paths that are perfect for birdwatching. For a quick and easy boardwalk trail, stroll along the Hellcat Interpretative Trail which is an elevated boardwalk through the marshes and dunes. 

If you are looking for a quirky landmark on Plum Island, visit the “ Pink House ”, an abandoned house built as a result of an ugly divorce in the early 1900s. The ex-wife desired to live in a copy of their formal home in Newburyport and the ex-husband agreed to build it for her- but put it in the middle of nowhere out of animosity!

Hampton Beach & Portsmouth, NH ~30 Minutes from Newburyport

New Hampshire is famous for its skiing, and fall foliage but also its gorgeous (although short) coastline. New Hampshire has 30 miles of coast between Massachusetts and Maine that offer quaint towns as well as lively beach activities.

Crossing into New Hampshire, I’d recommend first stopping by Hampton Beach State Park. This beach is very crowded during the summer as it’s a popular spot for families. It has nightly live music, weekly fireworks as well as the sand castle competitions and talent contests. You could easily spend an entire day here on the sandy coastline or you could stay in the RV park. Advance reservations required.

If you’ve had enough sun for the day, head up to Portsmouth New Hampshire. Portsmouth is a cute charming town with plenty of local shops and restaurants. Grab a bite to eat or stop in for a beer at a local pub.

Ogunquit, ME ~ 30 minutes from Portsmouth

Ogunquit Maine could be a perfect final destination if you don’t want to travel up the final 45 minutes to Portland. This quaint town of only 4 miles has spectacular ocean views as well as a charming town center. 

For a quick stop, I’d suggest taking the Marginal Way to Perkins Cove which is a mile long (each way) pathway along the coast. Stretch your legs and enjoy some beautiful vistas. If you plan on staying longer there are countless beach activities to enjoy such as sailing, fishing, or beachcombing.

The town center is also worth a visit! Stop by the Ogunquit Museum of American Art as well as countless galleries and boutiques.

Kennebunkport ~ 30 minutes from Ogunquit

The next stop on your Boston to Portland road trip should be Kennebunkport, one of the oldest towns in the U.S founded in the early 1600s. It has a coastal quaint atmosphere with the Kennebunk Port river running through town along its waterfront. 

I’d suggest stopping by Colony Beach as you can view boats coming into the town harbor. Stroll through the town center where you will find plenty of local art and shopping. Try some of the local fresh seafood- fancy another lobster roll?

If you have some additional time, I’d recommend exploring the ocean and taking advantage of the sailing, whale watching, and many other activities in Kennebunkport.

Old Orchard Beach ~ 30 minutes from Kennebunkport 

The pier at Old Orchard Beach is a must-see stop! The old-fashioned carnival-like pier sells street snacks like fried dough and cotton candy. Walk on the beach below for some cool views of the shops along the pier. 

Explore the town for more great food and shops. Keep the party going as there is mini-golf and carnival rides near downtown.

Cape Elizabeth, ME ~ 30 minutes from Old Orchard

While technically in Portland, Cape Elizabeth Maine is a perfect stop to see some quintessential New England lighthouses. There are three main lighthouses- Portland Head Light, Spring Point Ledge Lighthouse, and Bug Light. The lighthouses are pretty close together and shouldn’t take more than an hour or two to visit. If you only have time for one lighthouse visit the Portland Head Light, one of the most iconic landmarks in Maine.

Portland ~ 15 minutes from Cape Elizabeth

Once you finish your road trip to Portland you should definitely spend a day or two in Portland. Portland is absolutely worth a visit as the downtown is walkable and there is plenty to see.

Known for its thriving food and drink scene, you should tour the local breweries (try famous local brewery Allagash) or explore the seashore by taking a ferry to Peaks Island. Farther out from downtown, you will need a car to explore greater Portland. Eat all the food you can in Portland!

There is plenty more to explore in the Portland area from local beaches in Scarborough to the L.L. Bean flagship store in Freeport.  

What is the best time of year to visit Portland, Maine?

There really is no right time of year to do a Boston to Portland road trip! Crowds flock to coastal New England cities in the summer so expect busy traffic during the high season. In the summertime all the seasonal businesses- ice cream, snack shacks, beach restaurants, etc- would be open. After labor day in September, the seasonal tourist shops/businesses will close down and the towns may seem a bit quieter.

If you are looking to avoid crowds, spring or fall would be a beautiful time to stroll through charming towns or along the beach. The winter is also pretty but that coastal wind chill may dissuade you. Many beaches will allow dogs off-season so you could bring your canine friend. 

Getting to Portland from Boston without a car

There are a few options to get to Portland without a car including the Amtrak Downeaster or regional buses. Both options take about 2 hours, only slightly longer than driving. Perfect for a day trip or long weekend!

Amtrak to Portland

The Amtrak Downeaster takes 5 daily roundtrips from Boston’s North Station to Brunswick, Maine starting at 8:30 am. The trip via Amtrak takes about 2.5 hours with several stops along the way.

Train fares vary by destination but cost anything from $3-30 depending on the level of the ticket. Reservations are required before boarding. Bikes and small pets, with pre-booking and a fee, are allowed to board which means you could plan to bike around Portland!

There are lots of discounts for Downeaster tickets including 50% discounts for children and 65-plus seniors as well as medical care, veteran, and student discounts. Check before you book because there are often flash sales such as buy one get one half off, and group/family discounts.

Book ahead of time and maximize deals, and the Amtrak train can easily be the cheapest way to get to Portland from Boston.

Roadtrip via Train

You are still able to make a “road trip” out of the Amtrak ride to Portland. One of the first several stops would be in Durham, New Hampshire. There is a free shuttle (run by a nearby university) that takes people to Portsmouth. Portsmouth would be a perfect road trip stop for those who want to spend some time on the beach or taste some of the local seafood.

Another “road trip” option would be taking the train further to Old Orchard Beach for a day of swimming and laying on the beach.

Bus: Greyhound and Concord Coachlines

Another affordable way to get to Portland without a car is the Greyhound or Concord Coachlines bus. Tickets start at just $15 one way from South Station in Boston. Concord Coachlines, a regional interstate bus system, also offers direct service to Portland from Boston’s Logan airport.

The bus will not have the amenities- free wifi, and for-purchase snacks- that the Amtrak will have but may be a bit faster since there are no stops in between.

If you want to take the train right to Portland you will get dropped off in the downtown area near great restaurants and attractions. 

Boston to Portland Ferry

There is no ferry from Boston to Portland. But once in Portland, there are ferry options to Bar Harbor, ME or Canada.

In Conclusion: Boston to Portland

Boston Mass to Portland Maine can easily be done in a day but better to set aside a weekend to explore. Drive up and turn the journey into a road trip stopping at coastal towns in Massachusetts, New Hampshire and Maine. Dont have a car? Take the Downeaster Amtrack to Portland and explore restaurants and shops downtown.

There is plenty to do along the New England coast from visiting beaches, fishing, kayaking and seeing historic lighthouses. Visit the shops in charming towns and enjoy the quaint sealife atmosphere. And prepare yourself for some of the freshest seafood you’ve ever had. The lobster is an absolute must as its harvested right off shore!

You could even take the road trip a step farther and go north to Acadia National Park or Bar Harbor. Maine has so many destinations to offer visitors but a Portland road trip is a must!

• Meet the Team
• Work With Us
• Itineraries
• Italy Travel Guide
• Hawaii Travel Guide
• Travel Tips

Things to do

Boston to portland maine road trip.

Interested in doing a Boston to Portland Maine road trip? You’re in for a real treat. The total trip is only 110 miles and it can be completed in just under two hours, making it the perfect weekend getaway or day trip. Along the way, you’ll pass through picturesque towns, beautiful beaches, and stunning natural landscapes.

One of the best things about this road trip is the flexibility it offers. You can take different routes depending on your interests and time constraints. For example, if you’re short on time, you can take the quickest route via the highway. However, if you’re in the mood for a more scenic drive, you can take the coastal route, which offers breathtaking views of the Atlantic Ocean.

New England has always been at the top of my list of places I love visiting. Boston is a city rich in history and culture, with plenty of museums, landmarks, and restaurants to explore. Portland, on the other hand, is known for its picturesque harbor and copious amounts of lobster.

In order to find out what lies between these two cities, you need to go on a road trip and stop wherever the road takes you. It’s an exciting adventure that can be as busy or as relaxed as you want it to be.

Our team recently did a road trip in New England and we researched all the top spots to stop along the way, so we could lay it all out for you here. I hope you enjoy the journey as much as we did.

Table of Contents

Planning Your Boston to Portland Maine Road Trip

There are several routes you can take, including the Interstate 95, Route 95, and US-1. Each route has its own advantages and disadvantages, so it’s important to consider factors such as driving time, scenic views, and road conditions when choosing your route.

Interstate 95

Interstate 95 is the most direct route from Boston to Portland, and it’s a popular choice for travelers. The route passes through several towns and cities, including Portsmouth, NH, and Kennebunk, ME, and it offers scenic views of the New England countryside.

US-1 is another alternative route to Interstate 95, and it’s a good option if you want to explore some of the coastal towns along the way. The route passes through several towns, including Ipswich, MA, and Wells, ME, and it offers scenic views of the rocky Maine coastline.

Boston to Portland Itinerary

Before you leave Boston, make sure to explore the city . Boston is the capital of Massachusetts and one of the oldest cities in the United States . It is also the largest city in New England.

There are many things to see and do in Boston, but one of our favorites is exploring the Freedom Trail. The Freedom Trail is a 2.5-mile-long path that takes you to 16 historical sites in Boston, including the Massachusetts State House, Paul Revere’s House, and the Old North Church.

In a city defined by a rich history and vibrant sports culture, classic sports bars meet a thriving theatre scene around every corner. While there’s no way to see the best of Boston in one day, you can include these highlights on your first day:

• Walk the Freedom Trail past some of the most important sites that shaped the American Revolution
• Explore the Boston Tea Party Ships and Museums
• Head to the Italian cuisine-filled North End of Boston for either lunch or dinner
• Grab a few snapshots of America’s most photographed street, Acorn Street
• Visit the Boston Library and marvel at its exquisite architecture

Where to Stay in Boston

There are so many great hotels in Boston that you’ll be spoilt for choice, but this is the place we like to stay: The Newbury Boston . It’s a 5-star affordable luxury hotel in Back Bay that has an on-site restaurant and electric car charging stations.

Another of our favorites is The Godfrey Hotel, a 4-star hotel in Downtown Boston. It’s close to Boston Common and Faneuil Hall Marketplace.

Where to Eat in Boston

You’re going to have plenty of opportunities to eat lobster rolls on this road trip, but if you want to start in Boston, try  Yankee Lobster Company or Neptune Oyster  in the North End.

Other standouts you must try in Boston include Union Oyster House, the oldest continuously operating restaurant in the entire country, and Nautilus Pier 4  in the Seaport District for its great view.

Boston has a Timeout Market food hall, which is one of our favorite ways to try a lot of different things under one roof. Another market to hit up is Faneuil Hall Marketplace.

The route from Boston to Portland, Maine is not long, but there are a lot of great places to stop along the way, so it makes a great East Coast road trip. The distance between Boston and Portland is about 110 miles, and it takes about 1 hour and 45 minutes to drive.

I recommend taking the more scenic coastal route. You will be treated to stunning views of the Atlantic Ocean and charming coastal towns along the way.

This is the first stretch of road to tackle. Heading north on I-93/I-95. It’ll take about 35 minutes to reach Salem.

Infamously known for being the site of the Salem witch trials of 1962, the town is a global epicenter for everything occult. Here are some spots you shouldn’t skip:

• The Salem Witch Museum
• Salem Witch Trials Memorial
• The House of the Seven Gables

Portsmouth, New Hampshire

Portsmouth, New Hampshire is a charming and historic city located on the coast of New England. With its picturesque downtown, beautiful waterfront, and rich cultural heritage, it’s quite a popular destination.

The Memorial Bridge spans the Piscataqua River between New Hampshire and Maine. It is a World War I memorial dedicated to the sailors and soldiers of New Hampshire.

One of the highlights of a visit to Portsmouth is the city’s historic district. You can stroll along the brick sidewalks and admire the well-preserved colonial architecture. The district is home to several museums, including the Strawbery Banke Museum , which offers a glimpse into life in Portsmouth in the 17th and 18th centuries.

Another must-see attraction in Portsmouth is the Portsmouth Harbor Lighthouse . This iconic lighthouse has been guiding ships into the harbor since 1771 and is open for tours during the summer months.

The city is also home to several parks, including Prescott Park, which features beautiful gardens, a waterfront walkway, and outdoor performances during the summer months.

If you want to stay overnight here, reserve a room at The Hotel Portsmouth . This boutique hotel is located in the heart of downtown Portsmouth and offers comfortable rooms and excellent amenities.

Nubble Lighthouse

Between Portsmouth and Ogunquit you will find the Nubble Lighthouse. It was constructed in 1879 and sits on a large rock island offshore. While the island is not accessible to the public there are excellent views from shore and Sohier Park.

Ogunquit, Maine

Next, head back up to I-95 or Route 1 to Ogunquit. We loved this little town, however bad the traffic was to get through it. You can park in a side-street lot and walk to the center of town (it’s very small).

Stop in a few shops, like Revelations Gift Shop, Cricket’s Corner, and Sea Bags. Grab a coffee at OGT Beanery or an ice cream at Sweet Pea’s Ice Cream. Then take a walk down Wharf Lane to where you can see the popular Main Beach across the water. If you have time, you should definitely plan to spend a little time on the beach. There’s a great shallow bar and inlet that you can swim in.

Another popular attraction in Ogunquit is the Marginal Way. This scenic walkway stretches for about a mile along the rocky coastline and offers breathtaking views of the ocean. The Marginal Way is a great place to take a leisurely stroll or go for a morning jog.

Of course, no visit to Ogunquit would be complete without sampling some of the town’s famous seafood. There’s the Ogunquit Lobster Pound on Main Street and Perkins Cove Lobster Shack that’s been open since 1980. We also really enjoyed The Front Porch and it’s in a great location for popping in your way along this route.

Kennebunkport

We really enjoyed Kennebunkport. It’s one of the most quintessential New England towns with its historic architecture, scenic coastline, and vibrant arts scene.

The town is well-known for its maritime heritage, which you can explore through boat tours and the bustling Dock Square. Beyond the obvious, the town surprises you with hidden coves and tranquil beaches, making it more than just another tourist spot on the map.

However, there are a lot of tourist shops to pop into like the Lobstore, Beach Grass, and Copper Candle, and Good Earth. All very cute. If you’re getting hungry, grab a lobster roll at the Clam Shack (which is closed during the off season).

Another popular attraction in Kennebunkport is the historic district, home to several museums, including the Seashore Trolley Museum, which offers a glimpse into the history of public transportation in Maine.

Stop in to Batson River Brewing & Distilling and enjoy the view from their outdoor patios. They have a wide range of cocktails made from their small-batched spirits or enjoy a craft beer brewed on site.

Old Orchard Beach

Old Orchard Beach, Maine is a popular coastal destination that offers a mix of natural beauty and seaside charm.

One of the main attractions in Old Orchard Beach is its beautiful beach. The beach is over seven miles long and offers plenty of space for swimming, sunbathing, and relaxing. Visitors can also rent beach chairs and umbrellas, as well as bicycles, to explore the beach and surrounding area.

Another popular attraction in Old Orchard Beach is the classic boardwalk. The boardwalk is lined with shops, restaurants, and amusement park rides, making it a great place to spend an afternoon or evening. Speaking of amusement park rides, Old Orchard Beach has the last surviving beachfront amusement park in New England. Try your luck at the arcade games, ride the Ferris wheel, or enjoy a classic Maine lobster roll.

For outdoor activities, take take a scenic walk or bike ride along the Eastern Trail, which runs through the town and offers beautiful views of the ocean and surrounding countryside. The town is also home to several parks, including the Ferry Beach State Park, which offers hiking trails, picnic areas, and beach access.

If you’re looking for even more scenic views, head to Camden, ME, where you can hike to the top of Bald Mountain for panoramic views of Penobscot Bay and the surrounding area.

Portland, Maine

Congratulations, you’ve made it to Portland, Maine! This charming coastal city is known for its historic Old Port district, delicious seafood, and stunning views of Casco Bay. There’s plenty to see and do in Portland, so let’s dive in.

One of the most popular attractions in Portland is the Portland Head Light, a historic lighthouse that offers breathtaking views of the ocean. You can take a tour of the lighthouse and learn about its history, or simply enjoy the view from the surrounding park. In the distance, you can catch of glimpse of Ram Island Ledge Light Station.

East Port is known for it’s great food and drinks, and is the perfect place to stop for refreshments. There are several distilleries and breweries to choose from. We took a walk from one to the other on a nice evening and enjoyed quite a few of them.

Hardshore Distilling Company was a our favorite find. We all love gin and enjoyed a tasting. We happily grabbed a cocktail and some duck fat frites from the Friteshack next door and sat out on the patio. The perfect way to spend a summer evening in Maine.

If you’re looking to explore the city, head to the Old Port district. This historic neighborhood is filled with charming cobblestone streets, boutique shops, and delicious restaurants. You can spend hours wandering through the streets, taking in the sights and sounds of this vibrant area.

We took a guided walking food tour of Old Port to get a feel for it’s food and history. It was fantastic.

Another thing we really enjoyed was this Harbor Lights & Sights Cruise . It was a 2-hour cruise to see civil war era forts and 4 lighthouses.

Where to Stay in Portland

One popular choice is the Portland Harbor Hotel , a luxurious hotel located in the heart of the Old Port district. The hotel offers elegant rooms and suites, as well as a restaurant and bar.

During our recent visit, we opted for the Hyatt Place Portland-Old Port as our accommodation. The rooms are quite comfortable, featuring various layouts that include pull-out sofa beds to suit various needs. Plus, their valet service ensures convenient parking.

Restaurants in Portland

If you’re a foodie, then you’re in for a treat on this road trip. Boston and Portland are known for their vibrant food scenes, and you’ll find plenty of options to satisfy your taste buds. Some of the best restaurants to try on your road trip include:

• Luke’s Lobster : This place was so busy when we arrived that we almost didn’t stay, but we were able to find seats in the bar upstairs without waiting for a table. It’s a pretty casual spot with great lobster rolls and blueberry salads.
• Eventide Oyster Co. in Portland: This restaurant is famous for its lobster rolls and oysters. It’s a must-visit spot for seafood lovers.
• Duck Fat in Portland: This is a small spot in Portland that offers delicious rustic cuisine. They have a restaurant, but they also have a pop up that specifically sells their duck fat fries called Duck Fat Frites. Both spots are worth a visit.

Frequently Asked Questions

What is the distance between boston and portland, maine.

The distance between Boston and Portland, Maine is approximately 110 miles.

How long does it take to drive from Boston to Portland, Maine?

It takes around 1 hour and 45 minutes to drive from Boston to Portland, Maine. However, the driving time may vary depending on traffic and the route you take.

What are some scenic routes to take on a road trip from Boston to Portland, Maine?

There are several scenic routes you can take on a road trip from Boston to Portland, Maine. One route is to take I-95 and then take exit 19 for Route 109 towards Wells. This route takes you through charming coastal towns like Kennebunkport and Ogunquit. Another scenic route is to take Route 1A which runs parallel to the coast and offers stunning ocean views.

Is it better to drive or take the train from Boston to Portland, Maine?

It depends on your preference. If you enjoy driving and want to explore the coastal towns along the way, then driving is a great option. However, if you prefer a more relaxing and scenic journey, then taking the train is a good choice. The Amtrak Downeaster train runs between Boston and Portland and offers beautiful views of the New England countryside.

How many days should I plan for a road trip from Boston to Portland, Maine?

You can plan a road trip from Boston to Portland, Maine for a day trip or for a longer vacation. If you want to explore the coastal towns and enjoy the scenic views, then you should plan for at least 2-3 days. However, if you are short on time, you can do a day trip and still see some of the highlights of the route.

Be Prepared For Travel Planning is the most important part of any successful trip. Do it the easy way:

🧳 Travel Packing List | ✔️ Why You Need Travel Insurance | ✈️ What to Do Before You Leave Home

• Find and book the best hotel (our favorite booking site is Expedia)
• Research flight options (our favorite tool is Skyscanner )
• Book a tour (we always use Viator to find the best tours)
• Rent a car through Discover Cars (they search the best deals for you!)

YOU MIGHT ALSO LIKE

The Ultimate 10-Day New England Road Trip Itinerary

Essential Travel Guide to Boston, Massachusetts [Infographic]

15 Weekend Road Trips From Washington, D.C.

9-Day New York State Road Trip Itinerary

Like this post? Why not save it to Pinterest? FOLLOW US  on  Pinterest ,  Instagram ,  Facebook  for more great travel inspiration and tips.

Laura Lynch, creator and writer of Savored Journeys, is an avid world traveler, certified wine expert, and international food specialist. She has written about travel and food for over 20 years and has visited over 75 countries. Her work has been published in numerous guidebooks, websites, and magazines.

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

Save my name, email, and website in this browser for the next time I comment.

• Travel Resources

Fantastic Boston To Maine Road Trip Itinerary (2024 Guide)

• Last Updated: July 18, 2024

Looking for a scenic drive through New England? This Boston to Maine road trip itinerary will help you plan your coastal adventure!

There is no better way to explore New England’s sandy beaches, coastal towns, and lush forests than a road trip!

This Boston to Maine road trip takes you up through Massachusetts, New Hampshire, and Maine as you travel to Bar Harbor and Acadia National Park.

The itinerary includes historic towns, coastal gems, and all the iconic New England sights such as lighthouses, museums, beaches, islands, and more.

Get ready to breathe in that fresh sea air and feel the cool breeze as you embark on a scenic drive from Boston to Maine!

Check out our 3 Days in Boston Itinerary to help you plan your stay in the city.

Table of Contents

How long is a Boston to Maine road trip?

How long is a boston to acadia national park road trip, when is the best time of year for a boston to maine road trip, budget – holiday inn express, mid-range – hilton boston park plaza, luxury – the newbury boston, hampton beach, budget – la quinta by wyndham portland, mid-range – portland regency hotel & spa, luxury – the press hotel, budget – bar harbor villager motel, mid-range – bar harbor manor, luxury – sand bar cottage inn, acadia national park.

The exact duration of a Boston to Maine road trip depends on your destination! Maine is the largest state in the New England area, and there is lots of ground to cover.

So if you’re driving from Boston to Kittery, a town at the very southern tip of Maine, the drive is only 1 hour and covers about 60 miles.

You can make some stops in northern Massachusetts and New Hampshire along the way, but Boston to southern Maine would still only be a few hours at most.

But if you were driving from Boston to Van Buren, a small town at the northern tip of Maine, the drive is almost 7 hours and covers about 430 miles.

So it’s about 6 hours to just drive the length of Maine!

For this Boston to Maine road trip itinerary, the final destination will be Acadia National Park. This is the most popular road trip route from Boston to Maine. Not many tourists head further north than Bar Harbor unless they are road-tripping up to places in Canada such as Nova Scotia or New Brunswick.

Acadia National Park is about halfway up the coast of Maine. To drive directly from Boston to Acadia National Park, it’s 4.5 hours and 275 miles.

For this coastal New England road trip, the duration is about 7 hours and 320 miles including all the recommended stops. The road trip can take even longer if you choose to add more destinations or spend a decent amount of time in each place.

No matter how long you choose to make your road trip, you can fly into Boston Logan International Airport, rent a car, and hit the road! Boston has lots of car rental places all over the city as well if you’re not flying in.

The best way to get around is to rent a car and explore on your own! We recommend Rental Cars , which has the largest range of vehicles for the best value on the market.

Summer and autumn are the best times to complete any New England road trip. As you head north from Boston, temperatures get cooler so summer has the best weather for outdoor activities.

New England has lots of beautiful lakes, beaches, hiking trails, islands, and bays. Summer will have the nicest temperatures for swimming, hiking, camping, exploring, and taking boat tours. Summer is also the busiest time of year for a New England road trip, but it’s worth braving a few crowds to have warmth and sunshine.

Autumn is also a stunning time of year to road trip from Boston to Maine. Temperatures will start to cool off, which is great for hiking. Plus, you’ll get to witness some magnificent fall foliage as you drive through the forests!

Winter in New England is freezing and full of snow and ice. Driving conditions are not ideal in winter, unless you’re experienced at driving in the snow and you have a sturdy, 4WD vehicle well-equipped for winter.

New England is still beautiful in winter, and those looking for ski and snowboard destinations may prefer to do their road trip in the snow season. But for a coastal Maine road trip, summer and autumn are definitely the best times to travel.

Boston to Maine Road Trip Itinerary

So let’s dive into the Boston to Maine road trip itinerary! We’ll include all the best places to stop on the way from Boston to Bar Harbor.

Bar Harbor is the gateway to Acadia National Park, so either of these can be your final destination. Of course, you can continue to road trip further north and explore more of Maine and Canada! But northern Maine gets very remote, so for this road trip we’ll just be focusing on Boston to Bar Harbor and Acadia National Park.

Find more epic road trips from Boston to further explore the area!

As the capital city of Massachusetts, Boston is the largest city in New England. It’s also one of the most famous cities in the USA. Thanks to its American history, popular sports teams, unique neighborhoods, and charming waterfront, Boston has much to offer travelers.

Before you embark on your New England road trip, spend a few days enjoying the wonders of Boston!

Stroll through the historic Faneuil Hall Marketplace and grab a fresh lobster roll or search for souvenirs. Follow the Freedom Trail and check out the historic sites that played a vital role in the USA’s fight for independence. Have a picnic in Boston Common, cruise around the city on an educational Boston duck tour , or catch a show in the theater district.

Sports lovers can try to catch a game at one of the iconic sports venues in Boston. Check out a Boston Celtics game or Boston Bruins game at TD Garden or visit the famous Fenway Park for a Red Sox game.

Find more things to do in Boston with our complete guide!

Where To Stay In Boston

Before your road trip from Boston to Bar Harbor and Acadia National Park, spend at least a few days soaking in the history and culture of Boston. Here are some top-rated places to stay.

One of the more affordable hotels near downtown Boston is the Holiday Inn Express . Located in Cambridge, this budget hotel is conveniently located near the New England Aquarium, the Bunker Hill Monument and Boston Common.

A 4-star hotel in the theater district of Boston, the Hilton Boston Park Plaza offers accessible luxury for travelers. It’s right in the heart of the city and has lovely rooms equipped with all the amenities you need for a comfortable stay.

If you’re looking for some real luxury before you drive from Boston to Bar Harbor, check out the Newbury . An exquisite, 5-star property with elegant design and incredible amenities, the Newbury is right in Back Bay and is a fabulous place to spend a few days in the city.

• Distance from Boston: 30 minutes
• Driving time: 22 miles

From Boston, it’s time to start heading north towards Maine! Before leaving Massachusetts, stop in the northern city of Salem for an interesting historical journey through time.

This coastal city is best known for its legendary Salem Witch Trials of 1692, a period of hysteria that led to the execution of twenty individuals accused of witchcraft.

Today, Salem embraces its eerie past with numerous museums, historic sites, haunted ghost tours, and annual events that attract visitors from around the world. Learn about the craze of witchcraft at the Salem Witch Museum , the Witch Dungeon Museum, or the Witch History Museum.

Art lovers have to check out the Peabody Essex Museum , one of the oldest continuously operating museums in the United States. With roots dating back to 1799, the Peabody Essex Museum has a massive collection of art and cultural artifacts from different centuries and locations around the globe.

Other historic landmarks to check out in Salem include the House of the Seven Gables and the Salem Maritime National Historic Site. These showcase Salem’s maritime history rather than its witchcraft history. But as you can see, Salem is an amazing place to visit for those interested in art, history, and spooky stories!

• Distance from Salem: 45 minutes
• Driving time: 37 miles

As you continue north into New Hampshire from Salem, it’s worth stopping in Hampton Beach during the summer months!

This popular seaside destination in New Hampshire is known for its wide, sandy shores and vibrant boardwalk. For New Englanders looking for a beach getaway in summer, Hampton Beach is one of the best options.

This bustling beach area attracts visitors with its lively atmosphere, featuring a mix of entertainment, dining, and shopping options. There are arcades, bars, seafood restaurants, souvenir shops, and attractions for people of all ages.

You can also go swimming, surfing, jet-skiing, or try all sorts of water sports. Just remember, the Atlantic Ocean is pretty cold in New England! Even in summer, the ocean is very chilly, but it feels great on a hot summer day.

Hampton Beach is definitely a seasonal town and lots of things are closed outside of summer. So you may want to skip this stop if you’re doing the New England road trip before or after the summer months.

Read next: The Ultimate 3 Days in New York City Itinerary

• Distance from Hampton Beach: 26 minutes
• Driving time: 23 miles

Now that you’ve crossed the border from New Hampshire into Maine, you can start exploring the best Maine beaches, coastal towns, lighthouses, and attractions.

York is one of the oldest towns in the United States. It was established in 1638 and is rich with colonial history. Check out the well-preserved buildings in downtown York such as the Jefferds Tavern and the iconic Old York Gaol.

Other notable landmarks in York include the prominent Cape Neddick Nubble Lighthouse, which is one of Maine’s most photographed lighthouses.

York Beach is also one of the most famous Maine beaches, so this is a great place for a beach day in summer! York Beach is actually made up of both Long Sands Beach and Short Sands Beach, where you can enjoy sunbathing, swimming, and beachcombing. Short Sands Beach also has a charming boardwalk with shops and eateries.

You can also find some cool arcades, museums, eateries, shops, and historic buildings around York. It’s a lovely place to stop as you road trip through Maine.

• Distance from York: 45 minutes
• Driving time: 44 miles

The next destination is Portland, Maine one of the best places to visit on any Maine coast road trip. The iconic city is known for its craft breweries, great food, artistic atmosphere, and stunning Casco Bay scenery.

Those who love to eat and drink will have a blast exploring this foodie city! You can sample some of the best Maine craft beer or even join a culinary walking tour . All of Maine has amazing lobster rolls, but Portland is a great place to sample some fresh Maine lobster.

Other than food, downtown Portland is full of cool attractions. The Portland Museum of Art is the largest and oldest art museum in Maine. The Portland Observatory offers panoramic views of the city and coast, and the Old Port District has adorable shops, eateries, and charming cobblestone streets.

A sightseeing trolley tour is a fun and interactive way to sightsee and learn about the history and culture of Portland!

Those hoping to explore nature can venture out to Cape Elizabeth to stroll or bike through the greenery of Fort Williams Park. Here you can also find the Portland Head Light. As Maine’s oldest lighthouse , the Portland Head Light is an iconic landmark in New England.

You can also get great views of the lighthouse and the nearby islands from the water on a sunset kayak tour or a sunset cruise in Casco Bay. Portland is also a great place for a whale watching cruise between the months of May and October.

Check out the best things to do in Portland, Maine for more ideas!

Where To Stay In Portland Maine

There is so much to see and do in Portland, Maine that you may want to spend a few days here. It’s also conveniently located near the middle of a Boston to Bar Harbor road trip, so this is the perfect place to take a break from driving and explore one of Maine’s most famous cities. Here are some places to stay in Portland, Maine!

La Quinta by Wyndham offers affordable accommodation right near the hustle and bustle of Portland, Maine. It has free parking, free wifi, a swimming pool, a fitness center, and more!

Located in the iconic Old Port District of Portland, Maine, the Portland Regency Hotel and Spa is just steps away from the waterfront. In addition to amazing rooms, the 3-star hotel has a fitness centre, steam rooms, hot tubs and a full-service day spa so you can stay relaxed during your trip.

The Press Hotel, Autograph Collection is a 4-star hotel in downtown Portland, Maine. With a refreshingly modern design and a convenient location in the historic district, here you can treat yourself to an upscale hotel room during your Maine adventures.

• Distance from Portland: 37 minutes
• Driving time: 35 miles

From Portland, Maine, continue your road trip north! Bath is a lovely place to stop in Maine for anyone who is looking for charming towns on the rocky coastline.

Bath, Maine, is a picturesque town with lots of rich maritime heritage. Situated along the Kennebec River, Bath is often referred to as the “City of Ships” due to its long history of shipbuilding, which continues to thrive today at the Bath Iron Works.

Visitors can explore the town’s nautical legacy at the Maine Maritime Museum, which offers fascinating exhibits and boat tours . The Maine Maritime Museum showcases shipbuilding artifacts, maritime art, and historic vessels.

The town’s historic downtown area features beautifully preserved 19th-century architecture, quaint local shops, inviting restaurants, and scenic views.

Read next: 10 Incredible Things to Do in Montreal, Canada

• Distance from Bath: 35 minutes

Continue along the coast of Maine into Boothbay, another lovely coastal town known for its bustling Boothbay Harbor.

With colorful lobster buoys, historic buildings, and sweeping views of the ocean, Boothbay Harbor is a small but cozy destination on the wild Maine coast. The area is perfect for outdoor adventures including kayaking, sailing, and whale watching.

Get the best views of the islands and wilderness surrounding Boothbay Harbor on a lighthouses and islands harbor cruise . Or admire the soft pastels of sunset on a relaxing sunset sail . Either way, getting out on the water is a must in Boothbay Harbor!

Fresh seafood makes its way into Boothbay Harbor every day, so indulging in a lobster roll at Boothbay Lobster Wharf is another must-do.

For those who are more interested in history, check out cool local landmarks like the Burnt Island Lighthouse or the Boothbay Harbor Memorial Library. Put a fun twist on your sightseeing by joining a haunted ghost walking tour , where you can hear about pirate stories and visit historic sites like the Admiral’s Quarters Inn, Harbor House Inn, and the Opera House.

• Distance from Boothbay: 40 minutes
• Driving time: 24 miles

From Boothbay Harbor, continue up the east coast of Maine towards Bristol. This serene town on the Pemaquid Peninsula is known for its natural beauty and laid-back atmosphere.

The town is home to the iconic Pemaquid Point Lighthouse, one of Maine’s most photographed lighthouses, perched dramatically on rugged cliffs overlooking the Atlantic Ocean. Visitors can explore the grounds of Pemaquid Point Lighthouse, climb the tower for panoramic views, and learn about its maritime history at the nearby Fisherman’s Museum .

Pemaquid Beach Park nearby offers sandy shores perfect for swimming and picnicking, while nearby Pemaquid Beach is known for its beautiful sunsets and tidal pools full of marine life.

You can discover more of Bristol’s history at the Colonial Pemaquid State Historic Site , where the remains of a 17th-century English settlement and fort provide a glimpse into Maine’s early colonial history.

The quaint village center of Bristol features historic buildings, charming shops, and local eateries serving fresh seafood. Bristol Harbor is also a picturesque spot for watching lobster boats and enjoying waterfront dining.

• Distance from Bristol: 55 minutes

Drive about an hour north of Bristol, and make another stop in Camden, Maine. Sometimes called the “Jewel of the Maine Coast”, Camden is an adorable town nestled between the Camden Hills and the Penobscot Bay.

Camden Harbor is the center of the town. Filled with sailboats and yachts, Camden Harbor is a postcard-perfect location that captures the essence of coastal Maine.

The downtown area is also incredibly charming. Spend some time strolling around the scenic streets and checking out the shops, galleries, and eateries. You can even attend a show at the Camden Opera House or book a boat cruise through the harbor.

Check out the nearby Camden Hills State Park for some fresh air and greenery, which features over 30 miles of hiking trails. Hiking lovers can take on the popular trek to the summit of Mount Battie, which offers epic panoramic views of Camden Bay and surrounding islands.

Read next: 9 Spectacular Must-Do Day Trips From Boston

• Distance from Hampton Beach: 1 hour and 45 minutes
• Driving time: 76 miles

After about an hour and 45 minutes, you’ve reached Bar Harbor, the Gateway to Acadia National Park. Located on Mount Desert Island, Bar Harbor is surrounded by the sapphire waters and rugged islands of the Maine coast. It’s a truly stunning spot that will impress you before you even head into the national park!

Before exploring the wilderness of Acadia, get in touch with the history and culture of the town. Start at the West Street Historic District, a well-preserved collection of Gilded Age historic architecture that is on the National Register of Historic Places.

LaRochelle Mansion is an iconic landmark on West Street. You can learn about the mansion and the other significant places from a local guide on a historic guided walking tour !

Food lovers can join a culinary walking tour of Bar Harbor, and history lovers can visit the Abbe M useum to learn about the Wabanaki Nations and the Native American heritage of Maine.

Those more interested in exploring nature can walk along the scenic Shore Path that winds along the coast, or you can go kayaking and paddleboarding through Frenchman Bay. There is something for everyone in Bar Harbor!

Where To Stay In Bar Harbor

At the end of your Bar Harbor road trip from Boston, you have a few options for where to stay. As Bar Harbor is the gateway to Acadia National Park, many travelers will just stay in Bar Harbor for a few days and explore the park during the day.

You could also just pass through Bar Harbor and spend a few days camping at one of the registered campgrounds in Acadia National Park. But if you prefer more modern amenities and luxury at the end of your Maine coast road trip, here are some places to stay in Bar Harbor.

Stay right in the heart of Bar Harbor at the Bar Harbor Villager Motel . With free breakfast and a heated outdoor pool, you’ll be amazed at the amenities and cheap prices here!

This elegant and historic manor has landscaped gardens and a guest parlor with a fireplace, providing a cozy and heartwarming atmosphere. Bar Harbor Manor is located within walking distance of all the local attractions as well.

Just 800 metres from the beach, Sand Bar Cottage Inn is a 4-star hotel that feels more like a home. The rustic inn has excellent staff and all the amenities you need for a relaxing stay on your trip to Bar Harbor.

• Distance from Bar Harbor: 5 minutes
• Driving time: 1 mile

Acadia National Park, located mostly on Mount Desert Island on the Maine coast, is renowned for its stunning natural beauty and diverse landscapes. Established in 1916, it was the first national park east of the Mississippi River.

Acadia National Park is one of the most pristine wilderness areas in Maine and is full of gorgeous forests, granite peaks, and rugged coastal views.

One of the most famous features in Acadia National Park is Cadillac Mountain, the highest point along the North Atlantic seaboard. Here you can hike to the top and be among the first people in the United States to see the sunrise from October to March. It’s a good idea to complete the sunrise hike with a local guide , or you can also do the hike during the daytime as well.

Acadia’s extensive network of trails and carriage roads offers ample opportunities for walking, hiking, biking , and horseback riding. If you’re not a big hiker you can also just drive through Acadia National Park and admire the scenery from the car. Book an audio guide so you can ensure you hit the best spots!

Acadia National Park is also home to a rich array of wildlife. Visitors might encounter white-tailed deer, peregrine falcons, and a variety of marine life along the park’s rocky shores.

The park’s tide pools and coastal waters provide a habitat for numerous species, making it a prime location for wildlife observation and photography.

DISCLAIMER: Some of the links in this article are affiliate links, which means if you book accommodation, tours or buy a product, we will receive a small commission at no extra cost to you. These commissions help us keep creating more free travel content to help people plan their holidays and adventures. We only recommend the best accommodations, tours and products that ourselves or our fantastic editorial team have personally experienced, and regularly review these. Thanks for your support, kind friend!

Gabby Boucher

Hi, We’re Alesha and Jarryd!

We’ve been traveling the world together since 2008, searching for the planet’s best destinations and adventures.

Love Travel?

Sign up for our free weekly newsletter for the best travel tips, ideas and deals!

We respect your privacy. Unsubscribe at any time.

READ MORE...

The Ultimate 3 Days in New York City Itinerary (2024 Guide)

17 Best Road Trips From San Francisco, California (2024 Guide)

The Best Los Angeles To Grand Canyon Road Trip (2024 Guide)

Related Posts

The perfect 3 days in austin itinerary [2024], motorcycle adventure through glacier national park, 35 of the best things to do in moab, utah (2024), 21 best things to do in minneapolis, minnesota (2024 guide), leave a comment cancel reply.

Save my name, email, and website in this browser for the next time I comment.

Road Trip from Boston to Maine

Maine is known for its beautiful coastline and rugged inland scenery dominated by rivers, lakes and mountains. It's a great place to enjoy the great outdoors and is home to some of the country's oldest towns, where you'll find historic squares and quaint redbrick homes on the seaports looking out across the Atlantic.

The 960-mile road trip from Boston to Maine and back takes about 22 hours to drive. On the coast you'll pass York, Portland, Bar Harbor and Acadia National Park; then head inland to Bangor, Moosehead Lake, Greenville, Kennebec Valley and Bigelow Preserve.

This is a trip full of big, beautiful views, magical scenery and charming towns - the perfect ingredients for an unforgettable road trip. So, continue reading on the learn about the best route, our recommended stop and the best time to set off on this scenic adventure.

How far is Maine from Boston, and how long will the road trip take?

Boston and Maine are near neighbours, and you can make the 70-mile drive from Boston to York, Maine in just over an hour.

Once you've arrived in Maine, you'll have longer distances to cover, but fortunately, there's so much to see and do in the Pine Tree State that you'll find something to break up even the longest of stretches on your trip.

We'd recommend following our suggested round trip route below, which hugs the coast northeastwards as far as Acadia National Park then swings inland through Bangor to explore Baxter State Park, the Kennebec Valley and Maine Highlands.

This sets you up for a 775-mile circuit around the state which takes around 19 hours of driving, plus a little extra if you're making any extra side trips off our main route.

Add in a couple of hours for the drive back from Sebago Lake to Boston, and you're looking at a total of 22 hours 30 minutes for the complete, 960-mile road trip.

To help you with your route planning, we've provided more detailed driving distances further down the page.

You could drive the loop around Maine in just a couple of days if all you want is some great photographs and a lobster roll or two. But with so much to see, and hundreds of half or full-day hikes to choose from, we'd recommend taking at least a week.

Best road trip route from Boston to Maine

If you follow the interstate north from Boston, one of the first places you'll pass in Maine is York. Made up of four distinct towns – you might hear it called ‘the Yorks' – it's the perfect place to begin your tour around Maine.

With some of the best Maine Beaches right here, offering long stretches of sand, beautiful bays and stunning ocean views, where better to exit the interstate and begin to explore?

From here, you'll follow the Atlantic coast right the way to Acadia National Park, close to the Canadian border. This is a rugged and beautiful stretch of coast, so take your time exploring the inlets and islands that stretch out to the south of the highway.

Heading inland from Bar Harbor you'll soon find yourself driving through Maine's beautiful interior, where rivers, lakes, forests and mountains create a beautiful backdrop to any trip.

After passing Bangor and Medway you can enjoy views of Mount Katahdin, Maine's highest peak, and endless opportunities to enjoy outdoor pursuits, before the road starts to swing south again through the Maine Highlands and Kennebec Valley, passing Kokadjo and massive Moosehead Lake.

The circuit ends at Sebago Lake, one of the state's most popular destinations, and from here it's just a couple of hours back down the interstate to return to Boston.

Whether you're flying into Boston or you simply don't have your own transport in the city, renting a car for your road trip is something you'll want to take care of ASAP.

For an easy-to-compare view of rental options for your road trip from Boston to Maine, take a look at our partner site, RentalCars.com .

Road trip route from Boston to Maine: a round trip of the state

Follow Route 1 out of Boston then join the interstate heading north. Seeing as it's only a short drive up to Maine, you might like to detour towards the coast to visit Salem, Gloucester or Rockport along the way.

Otherwise, simply follow Interstate 95 (I-95) North all the way across Massachusetts and New Hampshire until you reach Portsmouth, where the Piscataqua River Bridge takes you into Maine.

Road Trip Route from Boston to Maine

Part 1: drive from york to ellsworth - a road trip through greater portland, mid-coast and downeast.

Once you've crossed over from New Hampshire to Maine, make your way north eastwards, keeping the coast on your right-hand side. You can either use the interstate here or hop onto the highway if you want to explore at a more leisurely pace.

You'll pass York and Kennebunkport before arriving in Portland, from where you'll take Route 1 to skirt around beautiful Casco Bay.

The highway then takes you on through Wiscasset and Thomaston. You might like to explore the miles and miles of rivers, inlets and rugged coast that sits to the south of the highway here, including Harpswell, Popham Beach, Georgetown Island and Boothbay Harbor.

Carrying on along Route 1 around Penobscot Bay, turn right when you reach Ellsworth and follow the road toward Trenton, where you'll cross the Mt Desert Narrows. Spend some time exploring Acadia National Park and Bar Harbor before returning along the route back to Ellsworth.

If you have a little extra time, detour east along Highway 1 here towards Schoodic Head, where the National Scenic Byway offers more fantastic views. Otherwise, simply continue up the highway from Ellsworth as far as Bangor.

Part 2: drive from Bangor to Greenville - a road trip through the Maine Highlands

From here, rejoin the interstate and follow it north as it runs parallel to the Penobscot River up to Medway. Then turn off the interstate and head towards Millinocket.

At East Millinocket you can take a detour up to North Penobscot to pick up the Katahdin Woods & Waters Scenic Byway, or continue on past Millinocket and join Golden Road on the narrow strip of land that separates Millinocket Lake and Ambajejus Lake.

Golden Road skirts the edge of Baxter State Park, where you'll find Mt Katahdin and dozens of amazing trails. Continue along Golden Road as it starts to swing back south again. When you reach Caribou Lake, which will be on your right, take the left fork and head towards Kokadjo and Greenville.

Here, you can spend some time exploring Moose Lake Scenic Byway, the Maine Highlands and the northern part of the Kennebec Valley, before continuing south through Abbot and Kingsbury Plantation to reach Bingham.

Part 3: drive from Kennebec River back to Casco Bay - a road trip through the River Valley and Lakes & Mountains

Follow the highway south the short distance to Solon, then turn onto Route 201A to cross the Kennebec River before taking Cross Town Road as far as Embden. Here, take Wentworth Road onto ME-16, continuing straight ahead onto Long Falls Dam Road where ME-16 swings round to the west.

With Gilman Pond to your left, continue on Long Falls Dam Road until you reach the southern tip of Flagstaff Lake. Here, you can park up to explore the trails of Bigelow Preserve or continue further along East Flagstaff Road to enjoy views out across the lake.

When you're ready to move on, return back along Long Falls Dam Road, turning right to briefly follow ME-16 west before taking a left onto the road to New Portland.

Next, head south past Farmington, Livermore Falls, Mechanic Falls and Casco, before continuing south onto Frye Island to enjoy some time on the shores of Sebago Lake.

From here, return to the highway, following Route 302 south as far as Riverton, where you'll rejoin I-95 to begin your drive back to Boston.

Best places to stop between Boston and Maine

Maine offers a fabulous blend of activity and relaxation, and there are some fabulous hotel stops along the route which let you combine the two seamlessly.

Watch the sunrise over the Atlantic in Bar Harbor

Around 8 hours and 30 minutes out of Boston, Acadia National Park is one of the must-see stops along this route and spending a night or two in nearby Bar Harbor gives plenty of time to enjoy the national park.

Ascend Cadillac Mountain, the first place in the US to see the sun each day (for 6 months of the year), or head to Thunder Hole where waves break impressively into a natural inlet. It's also a great place to see Maine's stunning fall foliage on display.

As well as being a gateway to Acadia National Park, there are great food and drink options in the town of Bar Harbor itself, and beautiful views out over the ocean. If you're lucky you might be able to see whales feeding in the bay here in summer.

One of the top hotels in town is Queen Anne's Revenge , a beautiful location known for its fantastically welcoming team, and for the immaculate design that runs through every room. You can really immerse yourself in the coastal vibe here.

The town was once a summer getaway for wealthy city dwellers, who helped to shape the streets into what you'll see today - take a walk through West Street Historic District to get a feel for the legacy they left behind.

Immerse yourself in nature in Greenville

On the northern stretch of the route, with around 8 hours of driving between here and Boston, Greenville is the perfect place to base yourself for a few days to explore parts of the Maine Highlands and Moosehead Lake.

Moosehead Lake is the biggest in Maine, surrounded by exquisite countryside views, and it offers some unique recreational activities. While you're here you should definitely take a moose-watching tour, where you'll try and track down these gentle giants in the wild.

You can take a steamboat cruise on Moosehead Lake to enjoy the views from a different angle, or enjoy boating, kayaking and fishing. Or head a little further afield to explore the Kennebec Valley, where you can go white water rafting or hike up to Moxie Falls.

If you're looking for a luxury retreat as you near the end of your road trip, the kind with sweeping lake views, immaculate design, unbeatable service and an excellent restaurant, then look no further than the Lodge at Moosehead Lake. A stay here really is an experience in itself.

With a luxury price point and a minimum stay requirement, this won't suit every traveler's road trip plans, in which case there are other options in the area.

As an alternative, we'd suggest Leisure Life, Greenville , which is spacious, and easy to get to from the highway. You can enjoy amazing views right out of the hotel and relax after a long day of hiking and driving in the hotel's bar or by the pool table.

Check out the coastal vibe in Portland

Portland is known for its cobblestone streets, red brick townhouses, Victorian mansions and thriving arts scene, so although you might have passed through Portland at the start of your trip, it's also a great place to spend a final night or two before returning to Boston.

Head to the Portland Museum of Art to catch a really varied and thought-provoking selection of exhibitions, ranging from contemporary pieces to works by some of art history's biggest names.

Then head to Portland Observatory. This ocean-facing signal tower is a reminder of Portland's maritime past, and all through summer you can take a guided tour to learn more about the city's ocean-going heritage.

Finally, before you hit the road, make your way to Old Port to enjoy the view out across the water one last time while you watch fishing crews haul in their catch of lobster.

Centrally located Portland Harbor Hotel stylishly combines modern design with hints of coastal chic , and it's a beautiful place to stay while you're in town.

There are some great cafes, bars and restaurants in the immediate vicinity, and most of Portland's main attractions are within walking distance.

Things to see on a road trip from Boston to Maine

You'll be spoilt for choice as you make your way around Maine - whether your preference is to spend time in the city, on the coast or exploring the great outdoors, there's something for everyone on this trip.

We've picked out some of the highlights, but one of the real pleasures of this route is the chance to stop off and explore the small towns, coastal scenery and big views that you happen upon as you drive.

Things to see on the way to Maine

• Salem, MA - Known for the infamous 17th century witch trials, this waterfront town has a number of witch-related museums and tours. You can also visit the Peabody Essex Museum, explore Salem Maritime National Historic Site, or head to the historic House of Seven Gables.
• Portsmouth, NH - The oldest settlement in New Hampshire is still a working port with plenty of history on display. Tour the historic houses, Strawberry Banke living history museum, or Seacoast African American Cultural Museum for different perspectives on the coast's history.

Things to see around Maine

• York - Head to York Beach for saltwater taffy and classic seaside fun, with Fun-O-Rama arcade, quirky cafes and live music, all looking out over Maine's beautiful sandy beaches and bays.
• Ogunquit - The town's name means ‘beautiful place by the sea' so enjoy a coastal walk or a stroll along one of America's best beaches. Ogunquit Museum of American Art is set in beautiful gardens by the sea (summer opening only).
• Broad Cove Reserve - Follow one of the walking trails here to enjoy more sea views from the sandy beach.
• Popham Beach State Park - Where the Kennebec River meets the sea you can swim, surf or stroll along the shifting sands at this popular state park. At low tide it's possible to walk out to nearby Fox Island, but keep an eye that the tide doesn't cut off the causeway before you return.
• Bath - Just outside the ‘city of ships' you'll find Maine Maritime Museum, or enjoy a fabulous seafood meal in one of the redbrick downtown restaurants.
• Reid State Park - Seabirds come here to nest in the dunes, rocks and sweeping sandy beaches which are also a fabulous place for humans to enjoy the coastline or hike up the headline for views across the park and islands.
• Augusta - Visit the Maine State Museum or the Old Fort Living History Museum to find out about the past of Maine's capital city. Then follow the River Rail Trail along the Kennebec River to enjoy beautiful views across the valley.
• Kennebec Valley - If you have time to take a fabulous scenic detour, head north from Augusta through Skowhegan, taking your time to explore the lower reaches of the stunning Kennebec Valley.
• St George Peninsula - Turn south from Thomaston to explore more of the region's rugged coastline, try some local wine, or visit the quirky Owls Head Transportation Museum.
• Rockland - Best known as the home of the Maine Lobster Festival, Rockland is also a meeting point for the arts, with Center for Maine Contemporary Art and the North Atlantic Blues Festival.
• Belfast - With its independent galleries, live music and Arts Walks, historic Belfast can be a buzzing place to stop if you're passing through in summer.
• Penobscot Narrows - Where the road crosses the Penobscot River, a massive observatory tower offers unbeatable views along the river and out to sea.
• Bar Harbor and Acadia National Park - This rugged and wild national park offers fabulous views out to sea, and is a haven for wildlife. It's one of the most-visited national parks in the country.
• Bangor - Stephen King is one of Bangor's most famous residents, and fans can take a tour of places that have inspired his work. Maine Forest and Logging Museum give a great insight into one of the state's most significant industries. And Cole Land Transportation Museum is a great place for fans of motor vehicles.
• Baxter State Park - To start exploring the Maine Highlands, head up to North Penobscot or Mount Katahdin for hikes to suit different abilities, as well as kayaking, fishing and climbing.
• Kokadjo - You'll find more moose per square mile in the area around Kokadjo than anywhere else in Maine – head to this tiny town's Trading Post for directions.
• Greenville - Follow the scenic byway along Moosehead Lake, where you can also hike or take a boat cruise.
• Bingham - Explore the northern part of the beautiful Kennebec Valley with a detour up Route 201 towards The Forks and Moxie Falls, Maine's highest waterfall. There's also great white water rafting on the river here.
• Bigelow Preserve - Faced with the proposed development of a huge ski resort here in the 1970s, Bigelow Preserve was established to protect this undeveloped area, where you can follow the northern part of the Appalachian Trail.
• Sebago Lake - This large lake is a popular destination for boating, kayaking, swimming and hiking and fishing – it's more than 300 feet deep which creates ideal conditions for trout.

Best time to go on a road trip from Boston to Maine

It's possible to visit Maine all year round, but depending on when you travel you'll have a very different experience. You'll encounter snowfall and freezing temperatures through the winter compared to temperatures in the 80s in summer!

With summer temperatures like these, you have the perfect set-up for hiking and outdoor activities, and although the ocean never gets very warm (60 degrees Fahrenheit), you'll still see people braving the chill.

You can also join in with the celebrations at Maine's many summer events, which include Old Port Festival in Portland in June, and Maine Lobster Festival in Rockland in August.

Don't expect to have the place all to yourself if you visit in summer though - Acadia National Park is one of the most-visited in the US, and popular towns and cities can get pretty crowded in August.

Also, keep in mind that conditions can change quickly along the coastal stretch of this route. There's a chance of big thunderstorms through summer, and it rains often (though usually not heavily).

Jumping forward a few months, there's no avoiding the fact that Maine is very cold in winter. Temperatures on the coast can reach the high 30s Fahrenheit at times, but inland you should expect temperatures below freezing, and as low as 10 degrees Fahrenheit, from December to January.

However, all that snow means that Maine is all set up for winter sports. With downhill skiing in the mountains, Nordic skiing through the forests, snowmobile trails and ice fishing, Maine can be a fabulous winter destination. However, some businesses do shut up for the winter, so it pays to be flexible.

Roads are kept as clear as possible, but always drive with the freezing conditions in mind, and apply extra caution if you're used to driving in more temperate parts of the world.

Spring takes a while to warm up and can be extremely unpredictable. Melting snow can bring slushy, muddy puddles, and temperatures in March are still usually below 40 degrees. By May though, you should see warm days (up to 65 degrees) and relatively low rainfall. If you're hiking, pack bug spray, as the rising temperatures bring out bugs that, although harmless, aren't likely to enhance your day on the trail.

If you do travel in spring, check out Kenduskeag Stream Canoe Race which takes place in Bangor in April - people travel from all over the country to join in this huge event. You can also enjoy the Fiddlehead Foodie Fest in Portland, a celebration of some of Maine's culinary delights.

Fall can be spectacular, particularly in the Maine Highlands, but be aware that October sees more rainfall than any other time of year. Daytime temperatures are pleasant, from the mid-70s in September down to around 60 in October, but evenings will start to feel cold.

It is a good idea to pack a warm sweater if you're planning on visiting Harvest on the Harbor in Portland.

September also might just be the ideal time to visit – with reduced crowds, warm days, and low humidity. By November, the foliage has fallen, the weather has turned, but the snow hasn't arrived yet, so we'd suggest this is definitely a time to avoid making the trip.

Driving times and distances between Boston and Maine

To help you with your planning, we've included more details about the driving times for the places we recommend trying to fit into your route:

Join our email list!

By joining our email list, you give LazyTrips permission to use your email for sending you newsletters, emails and updates including for marketing purposes. Your email will not be provided to third parties.

Related posts

Already have an account? Log in

Sidewalk Safari | Part-time Travel Blog

From boston to maine: the ultimate 3-day new england road trip itinerary.

Boston to Portland Maine Road Trip Map

Click on the image of the map below to open an interactive version in google maps with information on the drive from boston to portland, maine (and beyond) and maine getaway points of interest., new england road trip stop #1: newburyport massachusetts, new england road trip stop #2: portsmouth, new hampshire, new england road trip stop #3: kittery, maine and around, new england road trip stop #4: lunch in wells, maine, new england road trip stop #5: kennebunkport, main, new england road trip stop #6: biddeford, maine, new england road trip stop #7: portland, maine, things to do in portland maine , rwanda bean, portland head lighthouse.

Maine's Craft Beer Scene

"Beauty is in the eye of the beerholder"

Walk Portland

Dinner at david's restaurant, new england road trip stop #8: l.l. bean factory store, new england road trip stop #9: bowdoin college and around, new england road trip stop #10: maine maritime museum, new england road trip stop #11: land's end, new england road trip stop #12: giant's stairs trail, new england road trip stop #13: island candy company, new england road trip stop #14: potts point.

New England Road Trip Stop #15: Bath, Maine

Where to stay on a boston to maine road trip.

Did you enjoy this post about our Boston to Maine road trip? Sharing is caring...

FOLLOW SIDEWALK SAFARI PART-TIME TRAVEL BLOG$type=social_counter

• twitter|14.8k|followers|follow
• instagram|10.3k|followers|follow
• pinterest|4k|followers|follow
• facebook|835|likes|like

Featured In

Terms and Conditions

Privacy Policy

Boston to Maine Road Trip: Ogunquit, Freeport and Portland

Boston to Maine: the classic mini east coast road trip. As far as day trips from Boston go, it’s an easy, breezy state to visit in under a few hours. The best part is, you can hop in the car or take the train to many of the town and cities nearby, depending on your preference.

When I was growing up, we used to go to Maine all the time for family vacations. From Bar Harbor and Sunday River to Saco and Portland, I enjoyed locations up and down the east coast.

This year, I wanted to re-live some of the magic with my husband and plan our own Boston to Maine road trip. Being weekend warriors these days, we wanted to find and upscale, beautiful location less than three hours from our front door. He likes to hike and be outside (even in the winter!) and I also like a little luxurious comfort and fireside cocktails.

Maine’s Most Decadent: The Cliff House Resort and Spa

Have you ever entered a grand ballroom? Where the ceilings are high like palace, and there’s decadent detail in every corner? The Cliff House Ogunquit offers just this with a modern Maine twist.

While our beautiful room was cozy and decked out with traditional nautical décor, the real draw was the grand entrance of the hotel. It’s history dates back to the late 1800s, and has been a breathtaking place of tranquility ever since. Check-in the main lobby area, then descend down the staircase to be greeted with sweeping, floor-to-ceiling views of the cliffs and ocean waves. Maine does rugged seascape like no other, and the Cliff House has managed to bottle it up all in one panoramic vista.

Like most luxury resorts, the Cliff House offers amenities on-site to satisfy all tastes. Have a dip in the indoor pool, or try one of the two outdoor pools when weather permits. They also boast an outdoor heated hot tub for the brave who like to enjoy a snow winterscape surrounded by steam!

Most guests come to the Cliff House in Ogunquit to relax. You can get lost in a movie at their private theatre, or curl up with a book by the fireplace in the sunny lobby space.

Otherwise, indulge downstairs at the Cliff House Spa. Visitors can book various treatments to rejuvenate skin and polish up their toes. I appreciated the big robes to wear around the sauna and lounging areas too! Don’t forget a tea after your treatment overlooking the ocean.

The Cliff House has a few dining options on-site, such as the upscale Tiller Restaurant.

There you can savor lobster dishes any time of year, or try one of their generous appetizers over craft cocktails. I think the dessert of homemade cookies and blueberry ice cream was the highlight. Take your nightcap out to the lounge area for some live acoustic guitar on weekends.

You can also have a quick lobster roll at Nubb’s Lobster Shack or a morning latte at The Bald Head Coffee Co. But there’s also unlimited Keurig coffee and fresh local milk available on every floor of the hotel.

If you’d like to book your own getaway to Maine, check out these specials for the Cliff House – especially in the off-season.

The town of Ogunquit is just nearby as well if you’re truly itching to get off-property, but it’s not necessary.

More Pitstops on Maine’s East Coast

While Ogunquit, The Cliff House and even Kennebunkport nearby are enough for a trip in itself, you may want to do more. Within an hour are a few more options for day trips or overnights at your leisure.

Freeport : About an hour north is the cherry town of Freeport. What makes it most famous is the LL Bean flagship store . Well, multiple stores! Lots of people will stop there on their Boston to Maine road trip (or take the train too). Have a wander through the various retail buildings that go all-out in presentations, including a trout pond and lots of taxidermy animals. Other retailers have jumped on board too, so you can check out deals at Patagonia and Fjallraven.

Portland: UPDATE 4/14: I’ve been now! Portland is awesome! Take a look at our two Portland guides here and here with a little something for everyone. This hipster city lies between Ogunquit and Freeport.

Boston to Main Road Trip: The Route

It’s easy to reach the Cliff House Ogunquit from Boston. To drive, you follow Route 95 north about two hours from downtown Boston. Don’t forget a cheeky visit at the New Hampshire border to the liquor stores – there’s no tax!

If you decided to continue onto Freeport for shopping and strolling, it’s another hour. Have a quick breakfast before getting downtown at the Freeport Café – the fantastic home fries are worth the stop. You can stop in Portland too (or stay overnight) between the two spots as well if you have a few extra days.

Boston to Maine Train: Options for State-to-State Routes

While we didn’t take the train in this experience, it’s a great option for those who prefer to skip the drive. To get to the Cliff House (Ogunquit), you can take Amtrak from Boston to the Wells Amtrak Train Station. It’s about 7 miles by taxi to the hotel form there.

Or, you can go straight to Freeport and the LL Bean flagship store and start your trip form there. That’s also Amtrak ( the Downeaster line ) from North Station. It arrives in downtown Freeport for an afternoon of shopping. You can then hop back on the train to Wells, close to the Cliff House as your base.

Although I’m a road trip woman at heart, Amtrak changed my mind recently with a trip from Boston to NYC . I love that the trains often end right downtown, are smooth, and clean. If you book far enough in advance, it’s the same cost as a flight or even gas while driving. If you’re a weekend warrior too, those extra few hours with Wi-Fi on the train on your way from Boston to Maine might be a game changer, just don’t forget to  connect safely  to avoid any surprises while you’re off the grid later.

There you have it! Start your Boston to Maine road trip any time of year for a quick staycation. If you love to drive or take the train, start anywhere on Route 95 and head north!

Have a look at our great Boston to Miami road trip if you’re looking for an even longer adventure. Have you been to Maine? What’s your favorite part? What’s the best hotel you’ve ever experienced?

Hey there, I'm Eileen!

Welcome to Pure Wander, a blog community focused on all things traveling in packs! We aim to become the best resource for tips and tricks to plan your next group adventure!

Click here to learn what the rest of our team is up to!

Subscribe for Pure Wander Freebies

Pure Wander On YouTube!

Most recent posts.

• Embracing Joy: An Ode To Stowe, Vermont’s Delicious and Natural Wonders
• From Skinny to Wide-Leg: 10 Chic Ways to Wear Jeans on the Road
• Explore the Spirit Guides Exhibit at the Denver Botanic Gardens
• Jet-Set Savings: Building a Travel Fund for Your Dream Destinations
• Get Your Boating License with Offshore Sailing School, in Florida

Search the Pure Wander Travel Blog

pure_wander

🌍Profesh traveling hot mess for 20 yrs! 💅🏼 🌎Travel with family & friends✨ 🌎Different destinations beyond basics 🛩️ 🌏Inspo, guides, & deals 🖊️

Author Eileen Cotter Wright

Eileen Cotter is a freelance travel journalist and owner of Pure Wander. She's our resident expat extraordinaire and falls down a lot in yoga class. Follow her on Instagram @Pure_Wander.

Join the discussion 22 Comments

I haven’t been to Maine but that ice cream cookie looks wicked good. I did work my way through college at the LL Bean distribution center in Columbus Ohio (before I left to be an ostrich farmer but that’s another story). All of the goods that got damaged in shipping ended up at the employee only clearance store which had discount days on top of that. I think the last of my LL Bean clothing finally left my closet as we moved from San Diego to Orlando. That’s a pretty good run. The Cliff House looks like a beautiful property and we love sitting in hot tubs in the winter.

We drove from Boston to Maine in 2006 and loved every minute! I remember visiting L.L. Bean and having lots of yummy lobster rolls. We didn’t stay anywhere near as luxurious as The Cliff House. That would be a dream! Maybe another trip to Maine is in order.

I LOVE road trips! I did a New England road trip a million years ago but did not get as far north as Maine, I think I made it to Rhode Island from Boston. I need to go back and do MORE! This one looks like a lot of fun!

Having a luxury trip like you had is always exceptional. The classical road trip gave so much to learn and inspire people around the world. Thanks for motivating me.

As far as I know, Augusta is, or at least used to be, the capital of Maine, and not Portland.

The Real Person!

Good catch!

This is really interesting, You are a very skilled blogger.

It’s actually a great and helpful piece of information. I’m satisfied that you shared this useful info with us. Please stay us informed like this. Thank you for sharing.

Nice trip. Great pics that you are posting.

This road trip sounds like an absolute dream! The picturesque coastal drive from Boston to Maine, with stops in Ogunquit, Freeport, and Portland, promises a perfect blend of scenic beauty and charming destinations. I’m inspired to plan my own adventure along this route. Thanks for the fantastic travel inspiration

I just put the link of your blog on my Facebook Wall. very nice blog indeed.,’-”,

Your creativity knows no bounds! Every time you post, I’m reminded of how much I admire your talent and dedication. This is another masterpiece, and I can’t wait to see what you come up with next!

Leave a Reply Cancel Reply

Save my name, email, and website in this browser for the next time I comment.

• About Us – Pure Wander Travel Blog
• Group Travel Inspiration
• Copyright & Privacy Policy

Follow us on IG!

Find us on social.

© 2024 Pure Wander.

• Write For Us
• Daily Drop x Pure Wander: Top Cards for Miles & Points
• Dad Diaries
• North America
• South America
• Letters To The Editor

Recent Posts

10 day New England Road Trip Itinerary (Portland to Boston Drive)

Looking to spend some time on the east coast by taking a road trip through new england this road trip itinerary will take you through some of america’s oldest cities and towns..

Get ready to be blown away by idyllic small-town vibes, white steeples with brick-red facades, fresh lobster rolls, whale watching, and history upon history on this New England road trip!

This New England road trip will take you from Portland, Maine up to Acadia National Park, then back down through Portsmouth and into Boston, Massachusetts.

🚗 When booking your New England Road Trip car rental online, I recommend using Discover Cars . They provide the best deals for car rentals in New England!

Prepare for yourself for this New England road trip by making sure you have all the gear you need to make the best of your time in the car!

Let’s jump in!

Quick Overview of the New England Road Trip Itinerary

Boston to portland maine map.

A quick summary of stops on your 10 Day New England Road Trip Itinerary

• Days 1-3: Portland, Maine (3-hour drive time on day 3)
• Days 3-5: Acadia National Park, Bar Harbor (4-6 hour drive time on day 5)
• Days 5-10: Portsmouth, New Hampshire, and Boston, Massachusetts
• Airports: Portland International Jetport in Portland, Maine (PWM); Logan International in Boston, Massachusetts (BOS)
• Transit: Rent a car for pick up at PMW and drop off at BOS

New England Road Trip Itinerary

The new england road trip itinerary days 1-3: portland, maine.

• Land at Portland International Jetport early in the day if possible and pick up your rental car
• You’ll want to book your stay for 2 nights in Portland

Where to Stay in Portland, Maine

The best accommodation option would be to stay in or very close to Old Port. This is the historic downtown area of Portland with many cute boutiques for shopping and restaurants within walking distance.

If the prices in this area are out of your budget, I would recommend staying at an accommodation in either Portland’s East End or West End as they are both near the heart of Portland, Old Port.

• The Portland Harbor Hotel | cute boutique style
• The Press Hotel | sleek and upscale style
• The Courtyard by Marriott Downtown/Waterfront | cost-effective option near all the fun sites

Day 1: Landing in Portland, Head Light, and Old Port

• Today you’ll see some great highlights of Portland including the lighthouse and Old Port
• Portland city drive time: 15-30 minutes around town, including the airport to Old Port

Start your morning off with breakfast at Becky’s in the West End. The blueberry pancakes are DELISH, however, the omelets are also great for a high-protein meal.

• Becky’s Diner | Address: 390 Commercial St, Portland, ME 04101

After breakfast, head over to Portland Head Light State Park for a short hike! This is one of the most popular sites in Maine and offers incredible views out over Casco Bay.

You can even do a lunch picnic here! Wear walking shoes (or sandals if you’d like to hike down to the water) and do some rock climbing to get some beautiful pictures of the Portland Headlight.

Spend as much time as you want here–it’s so beautiful! (We came here twice!)

Pro-tip: Tie up your hair and bring a jacket as it’s pretty breezy and a little chilly here!

• Portland Head Light State Park | Address: 1000 Shore Rd, Cape Elizabeth, ME 04107

In the afternoon, take an hour-long tour of the Wadsworth-Longfellow House which was Maine’s first house museum that opened up to the public. Longfellow was a national literary man of his time and most furnishings in his house are original or belonged to his family.

• Wadsworth-Longfellow Museum | Address: 489 Congress St, Portland, ME 04101

After getting your history fix, you can take a walk and explore Old Port. This area has many cute boutiques and fun restaurants to try out!

Stop by The Holy Donut for a delicious snack (even multiple times over a 2-day trip) with interesting flavors such as the Maine blueberry cake donuts or chocolate sea salt flavor.

• The Holy Donut | Address: 177 Commercial St, Portland, ME 04101

There are also so many restaurants lined up here that you can grab a quick lunch before doing all your shopping. Some recommendations include Duckfat (amazing Belgian-style fries with sauces) and The Honey Paw (ramen noodles and Asian infusion).

Or head over to the Maine Lobster Shack for a delicious lobster roll–nothing is better than this fresh-caught lobster. You can’t go wrong with the Maine Lobster Roll or the Brown Butter Lobster Roll, and try the Maine Root Soda while you’re here.

• Maine Lobster Shack | Address: 425 Fore St, Portland, ME 04101

Day 2: More of Historical Portland and Peak’s Island

• Today you’ll get some more historical experiences of Portland and explore Peak’s Island by ferry
• Portland city drive time: 10-15 minutes around town

The next morning, grab some breakfast at the Bayside American Cafe. With their delicious menu, you can’t go wrong – everything from Maine blueberry pancakes to Bayside eggs benedict!

• Bayside American Cafe | Address: 98 Portland St Portland ME 04101

After breakfast, check out another museum for the history buff: reserve a ticket to spend about an hour touring Victoria Mansion, a historical landmark that is one of the oldest in the country and known for its architecture and original interior design.

• Victoria Mansion | Address : 109 Danforth St, Portland, ME 04101

After touring the mansion, grab lunch at Hot Suppa! This Southern diner (and what I would consider hipster) has delicious offerings such as the Mother Clucker.

• Hot Suppa | Address: 703 Congress St, Portland, ME 04012

After getting a good bite in, take a 17-minute ferry to Peaks Island for some more exploring; we spent half a day here and had so much fun!

As you get off the ferry, rent a little golf cart From Mike’s Carts to get around the area. You can grab Lisa’s famous cinnamon bun at Peak’s Café as you start your cart tour.

Use this map to help you navigate your way around Peak’s Island. Head north first so that you can end your drive on Seashore Avenue, which provides endless views of the ocean.

Partway through your drive on Seashore Avenue, you can park your cart along the road and take a short hike to Battery Steele, which used to be a military fortification now graffiti-covered.

If you have time, you can also drive around the neighborhood and check out some of the cutest coastal homes–make it a game to find the best-named house!

You can also check out the Fifth Main Museum on the island as well to learn more about the history of the Civil war and other exhibits.

Keep track of the ferry schedule so you don’t miss the last one! Before you go, grab an ice cream cone from Down Front, a small convenience store.

• Ferry to Peak’s Island | Address : 56 Commercial Street, Portland, Maine 04101

Day 3: Close Out Your Portland Itinerary and Drive 3 Hours Toward Acadia

• Today you can choose your morning experience and then prepare for your drive to Bar Harbor
• Portland to Bar Harbor drive time: 3 hours

You can pack everything the night before and check out as you leave in the morning. Start off the day by heading back to Old Port to grab some snacks and breakfast in preparation to drive out.

Since you’ll be savoring your last moments in Portland, Maine, you can choose what you’d like to do:

• last-minute souvenir shopping in Old Port
• taking some last looks at Portland Headlight
• check out the Portland Museum of Art

You will want to leave Portland by 1 PM.

• Portland Museum of Art | Address: 7 Congress Sq, Portland, ME 04101

That’s everything for your 3 day Portland itinerary ! It’s about a 3-hour drive west to your next stop so you’ll want to have all your favorites (snacks, music, and conversation topics) ready to go!

The New England Road Trip Itinerary Days 3-4: Acadia National Park and Bar Harbor

• When you arrive in Bar Harbor, check into your hotel and get some dinner in town
• You’ll want to book a 2-night stay in Bar Harbor

Where to Stay in Bar Harbor

For accommodations, stay directly in Bar Harbor at a cute inn to get the best of your time. Keep in mind that cell service around these parts is spotty at best, so don’t be afraid to stop and ask for directions!

• The Inn on Mount Desert | affordable stay in Bar Harbor
• The Elmhurst Inn | old-fashion boutique style in Bar Harbor
• Acadia Hotel – Downtown | upscale stay in Bar Harbor

Day 3 Continued: Getting to Bar Harbor and Settling In

• Spend your time strolling through this charming small town
• Portland to Bar Harbor drive time: 3 – 3.5 hours

Continue your New England road trip itinerary and head west towards Bar Harbor, where Acadia National Park Pond is located. You should arrive in the afternoon and get lots of views of lakes and beautiful nature scenes.

Since you’ll be here later in the afternoon, head into Bar Harbor which offers a small-town feel and is a fantastic place to enjoy some delicious food.

We got ice cream cones every time we went (which was only twice!). While you’re at it, make sure to buy some snacks, maybe even a sandwich lunch to enjoy while in Acadia National Park Pond the next day.

This would be the time to grab souvenirs or do some window shopping in Bar Harbor. There are so many cute boutique shops to just browse through!

For lunner (lunch + dinner), Galyn’s is a cozy little seafood restaurant in a Victorian-era house that has options for outdoor seating.

Opt to sit out on the patio and enjoy the fresh air and views while you eat your clam chowder soup. If that’s not for you, they also have small plates, fettuccine, sandwiches, and many more options to choose from. It was wonderful!

• Galyn’s | Address : 17 Main St, Bar Harbor, ME

Day 4: Explore Acadia National Park Pond

• Get an early start at Acadia National Park and do all the exploring on the hiking trails and beaches
• Bar Harbor to Acadia drive time: 15 – 30 minutes going through the park

Continue your New England road trip and get an early start to Acadia National Park Pond, which is known as the “Crown Jewel of the Atlantic Seaboard” and it’s easy to see why.

Take your time in Acadia and explore all that it has to offer, you won’t be disappointed! The mountain views are incredible, the road is scenic and well-maintained.

The weather in Acadia is usually pretty nice, but it can get chilly in the evenings. Make sure to pack layers so you’re prepared for everything! I had a light jacket with me, but by midday, I was getting pretty warm from the sunshine and hiking.

One of my favorite hikes here is the Beehive Loop , which is a great way to get acquainted with the difficult trails.

If you are looking for an adventurous hike, this 450-foot cliff trail will get your heart pumping! As one of Acadia’s most popular hikes, expect steep granite staircases that challenge even experienced backpackers (think ladders and iron rungs), as well as exposed cliffs. The trail is about 1.4 miles roundtrip and can take anywhere from 1-3 hours.

Another more moderate hike is the Bubble Trail which branches into North and South.

Both trails are reasonable, but if you’re looking for a shorter trail, take the Bubble Rock trail to see “the bubble,” which is a huge rock shaped like a bubble sitting precariously on the cliff of the mountains.

If mountains aren’t your thing and you’re more of a beach lover, Sand Beach and Echo Lake Beach are great for swimming and hanging out. You’ll most likely come across Sand Beach first if you’re coming from the entrance at Bar Harbor, which will also bring you to the trailhead of the Beehive Loop.

At the beach, you can unpack your lunch and enjoy a nice view out into the ocean with the sun keeping you warm.

However, if you are hungry after your hiking expedition, enjoy lunch at Jordan Pond House where you can dine on traditional meals of New England that include lobster rolls, chowder, and more.

A popular fare here is popovers and tea and if you are like me who had no idea what a popover is… it’s a light roll made of egg batter and can be eaten with whipped cream or jam and tea. Delish!

• Jordan Pond House | Address : 2928 Park Loop Rd, Seal Harbor, ME 04675

For more adventuring in Acadia, make the drive to Cadillac Mountain or Thunder Hole. Cadillac Mountain is the tallest mountain on the East Coast at just over 1,500 feet with unparalleled views over Frenchman Bay and beyond.

Finally, no road trip to Acadia National Park is complete without a stop at the famous Thunder Hole! Don’t forget your raincoat because it looks like thunder when waves crash into rocks down below, causing an amazing sound experience for visitors nearby.

After a long day exploring Acadia National Park head back towards Bar Harbor at night to enjoy dinner in town. Grab a seat at one of my favorite restaurants, the family-owned Side Street Cafe.

The staff is so welcoming and the restaurant really fosters an atmosphere of community. Everything here is amazing–from appetizers to sandwiches and burgers.

• Side Street Cafe | Address: 49 Rodick St, Bar Harbor, ME 04609

After all the energy spent at Acadia, get some much-needed rest before the long 5.5-hour drive to Boston!

The New England Road Trip Itinerary Days 5-10: Boston, Massachusetts (with a stop in Portsmouth)

Where to stay in boston.

Driving around Boston can get congested during peak traffic hours, which will make your trip take longer than expected if you don’t plan accordingly.

Because of that, we decided to stay outside of Boston proper. Our Airbnb was about a 30-minute drive to Boston, which was actually more cost-effective for us since we weren’t always going to be in Boston proper.

If you would prefer to stay in Boston, you may be able to save on driving time on congested roads.

• Hampton Inn Boston Logan Airport | 16-minute drive to Boston, typical hotel stay
• The Newbury Boston | 3-minute walk to Boston proper, upscale stay

Day 5: Make the 5.5-hour drive South to Boston, with a short stop in Portsmouth, NH

• Check out of your rooms and prepare for a long drive south to Boston
• You’ll want to book your rooms in Boston for 5 nights
• Bar Harbor to Bass Harbor Light Station Drive time: 30 minutes
• Bar Harbor to Portsmouth Drive time: 3 hours, 55 minutes
• You’ll make a lunch stop in Portsmouth and get the chance to explore for a short while
• Portsmouth to Boston drive time: 1 hour

As you continue your New England road trip itinerary and start your drive down to Boston, you can make a stop at Bass Harbor Light Station. This historic lighthouse is off the beaten path but definitely worth checking out if you would like to add another lighthouse to your list!

After taking some pictures of the lighthouse, continue on your New England road trip and make a stop in Portsmouth, New Hampshire.

With a population of approximately 21,000 people, Portsmouth is the 13th largest city in all of New England! It’s also home to the Strawberry Banke Museum which consists of 11 historic homes and buildings dating back as early as 1695.

You can grab lunch in Portsmouth from places like the Clipper Tavern, The Wilder, or The Franklin.

If you’re game for ice cream (which is always on my list), check out Annabelle’s Natural Ice Cream, made with only the best ingredients! Then take a walk down the main street and explore the town on foot.

• Annabelle’s Natural Ice Cream | Address: 49 Ceres Street, Portsmouth

You’ll see an iconic New England church and steeple right in the town center. Right along this street are some cool shops like the River Run Bookstore, a fun game store called Diversions and Games, and a cute international boutique shop, Ten Thousand Villages.

After walking through some shops and exploring a little in Portsmouth, hop back in the car and finish out your New England road trip in Boston!

Next up on your New England road trip: Boston!

Day 6: Walk the Freedom Trail

• You’ll explore the freedom trail on foot and really get to see all the history in Boston proper – prepare yourself, it’s a long day of walking!
• Boston city drive time: 15-30 minutes depending on your stay

Take the rest of the days and go at your own pace. In this section of the New England road trip, you will not be driving across state lines or going long distances anymore.

There is SO much to see that you’ll need to make your itinerary work for you! Consider your top historic sites and your level of energy for all the walking you might do in the city. With that said, let’s jump into exploring Boston!

Boston is home to so much history! On the top of your list to do in Boston, the Freedom Trail .

This trail is a must-see for anyone who visits the city! The Freedom Trail is a self-guided historic walking trail that leads you to 16 of Boston’s most iconic landmarks. It is 3 miles long and will take you a whole day to complete as you make stops along the way.

You’ll want to get started on the Freedom Trail in the Boston Commons (1) . From here, you can visit the information center to get yourself a map and ask any questions. You’ll know you’re on the trail by following the marked trail embedded in the sidewalk.

As you get started, you’ll see the Massachusetts State House (2) located on a hill, and following that will be Park Street Church (3) , which was one of the first landmarks travelers would see coming into Boston.

Next, you’ll come upon the Granary Burial Ground (4) , which has some of the most influential historic persons like Benjamin Franklin’s parents, Paul Revere, and John Hancock. After this you’ll come upon a small square where you can visit King’s Chapel & King’s Chapel Burying Ground (5) , which is America’s oldest running pulpit – the bell still rings to call worshippers into the church.

You’ll also see Benjamin Franklin’s statue (6), the Old Corner Bookstore (7), and the Old South Meeting House (8) where the Boston Tea Party began!

At this point, you are right in the middle of a commercial hub to grab lunch – we got the familiar and ordered a burrito at Chipotle. However, there are so many restaurants to choose from.

Continue your trek on the Freedom Trail after lunch to the Old State House (9) , which is Boston’s oldest standing public building.

The trail will then take you to the site of the Boston Massacre (10) of 1770 where the Redcoats and Boston civilians broke out in gunfire. You’ll see the site marked with a marker.

Next up is Faneuil Hall (11), the “home of free speech” and “cradle of liberty,” you’ll see the popular golden cricket weather vane. It is now a cool marketplace and is one of Boston’s most popular attractions!

There is something for everyone with its many shops, restaurants, and music venues all in an old-fashioned market atmosphere. Right outside the marketplace, you might spot jugglers and dancers giving a great show!

After a little shopping, you’ll continue walking towards Paul Revere’s home (12) where you can take a tour inside. Continue your trek on the Freedom Trail to the Old North Church (13) , where you’ll see a statue of Paul Revere – this was the site of his midnight run.

You can also grab a snack in this area at Mike’s Pastries as he has some of the most delicious cannolis (address mentioned below)!

After the Old North Church, you’ll come to Copp’s Hill Burying Ground (14) , which is the final resting place for many artisans and craftsmen in the North End of Boston.

You’ll then take a 20-minute walk towards the USS Constitution (15) , which is the oldest commissioned warship afloat that fought during the war of 1812. Today, it is managed by the US Navy. You can purchase tickets and actually walk on the ship and even go underdeck to see the cannons and rooms.

Finally, head towards the last site of the Freedom Trail, Bunker Hill Monument (16) , which is a 221-foot granite obelisk.

At this point, it is likely that you’re well into the afternoon so I would recommend booking an Uber to drive you back to the Boston Commons, which is most likely where your car is parked.

If you would rather continue walking, you could walk the 3 miles back toward the commons.

From here, you can choose a place to grab dinner and call it a night! You’ll be exhausted from all the walking and sightseeing you’ve just completed.

Day 7: Whale watching, Boston Harbor, and the North End

• After all the walking yesterday, take it easy and go whale watching
• Explore the Italian district of the North End

Boston is the perfect place for whale watching ! There are several tour companies along the water where you can book a trip to see the whales.

The best time to see the whales in Boston is during the months of May – October when the whales migrate during the warmer temperatures.

Book your Boston whale-watching tour!

Boston Harbor Cruises has experienced marine biologists and tour guides to give you information while you are on the cruise. They are also experts in knowing the best spots where whales like to hang out.

You’ll head to Long Wharf, which is near the New England Aquarium to get in line for the tour. On our whale-watching expedition, we went to Stellwagen Bank National Marine Sanctuary.

It took a few minutes of watching, but we did spot some whales!

A whale-watching tour can take anywhere from 3-4 hours. Wear a jacket as it will get cold when you’re in the middle of the ocean.

• New England Aquarium | Address: 1 Central Wharf, Boston, MA 02110

After your tour, you’ll be right in the Boston Harbor. From here, you can walk along the waterfront and explore some sites. You can relax at the Charles River Esplanade which is a walking path along the waterfront with plenty of benches.

If you would like some more Boston history, check out some of the museums such as the Museum of Science, the Boston’s Children Museum, or the Boston Tea Party Ships and Museum.

For dinner, head to the Italian quarter in the North End which is the oldest neighborhood in Boston and has some of the most delicious food.

If you’re not into Italian food then there is still plenty of great places to try out including sushi, burgers, or lobster rolls that are sure to please everyone in your road trip group!

For dessert, try out the cannolis at Mike’s Pastry as they have been making these delicious pastries since 1926. The lines can look intimidating as they go out the door, but it goes quickly and the staff is very aware of your status in line.

• Mike’s Pastry | Address: 300 Hanover St, Boston, MA 02113

Day 8: Harvard University and Candle Pin Bowling

• Explore the college town of Harvard University
• Have fun candlepin bowling
• Boston to Cambridge drive time: 30 minutes – 1 hour depending on your stay

Boston is also home to many amazing colleges and universities. On this day of the New England road trip, we chose to take a visit to Harvard.

Start off by grabbing brunch at Le’s Vietnamese restaurant then check out the historic Harvard Bookstore.

After this, we wanted to take a walk around the Harvard Campus. Do note that visitors aren’t allowed within the buildings without a guest pass.

We just walked around the campus and noted the buildings as well as the plaques that were displayed. It was pretty cool to say that we went to Harvard!

If you’d like to experience Harvard University more deeply, you can book a 70-minute student-led tour to see everything the university has to offer. Either way, you’ll want to make sure that you don’t miss out on visiting Harvard Yard.

There are also three art museums and the Harvard Museum of Natural History to explore.

Book your Harvard Walking Tour

For a more relaxed New England activity, go candlepin bowling at Sacco’s bowling alley in Sommerville, which is about a 10-minute drive from Harvard University.

This type of bowling is a little different than what you might be used to. Candlepin bowling is played with smaller balls and the pins are thinner as well; it tends to result in more strikes which means more points!

Sacco’s does offer food for purchase so we ordered flatbreads off their menu for dinner.

• Sacco’s Bowling Haven | Address: 45 Day St, Somerville, MA 02144

Day 9: Fenway Park, New England Holocaust Memorial, Boston Public Market, Cheers, and a Ghost Tour

• Revisit Boston proper: there is so much more to see that might have been missed on the Freedom Trail – take your last day to visit all those last sites
• Boston city drive time: 15-30 minutes depending on where you stay

I’m not much of a sports fan, but I really enjoyed a walk around Fenway Park where the Red Sox play.

It was built back in 1912 and has been around ever since, also displaying members of the team around the stadium. With a guided tour, you’ll be able to visit the stadium’s collections of photographs, artifacts, and more!

Boston also has a memorial for the persecuted Jews during the Nazi regime where you can visit the New England Holocaust Memorial.

After walking through the memorial, you’ll end up near the Boston Public Market, which is filled with produce and gourmet food. This is the perfect spot to grab lunch!

• New England Holocaust Memorial | Address: 98 Union St, Boston, MA 02129
• Boston Public Market | Address: 100 Hanover St, Boston, MA 02108

If you’re a huge literary fan, you can visit the Edgar Allan Poe statue, which is so descriptive and very well-made. You can see one of his most notable works: The Tell-Tale Heart. The statue stands right across the street from the Boston Commons south of Boyleston Street.

Another iconic stop in Boston is to visit the Cheers restaurant filled with memorabilia from the show! It’s located on the other side of the Boston Commons where Edgar stands. You can grab dinner here and reminisce about the show.

• Cheers restaurant | Address: 84 Beacon St., Boston, MA 02108

For the brave, book a trolley ghost tour to hear bout Boston’s most haunted locations! The tour guides are historians, so you can be sure that the stories they tell will be accurate and interesting-we learned so much about the cemeteries and ghost sightings!

Fun fact: there’s a little girl who is regularly spotted right next to these gravestones!

Side Note: You can also spend one night in a historic hotel or B&B. Some of these places date back to the 1800s! Most hotels even offer their own ghost tours if you’re feeling brave enough to stay overnight at one of their historical spots.

As you hang out later in Boston, you can see the Massachusetts State House beautifully lit up in the night sky! You can grab dinner to go and have a picnic in the Boston Commons, which is a huge park area.

Day 10: Check out and return home

• Boston to Logan Airport drive time: 15-30 minutes depending on your stay

After exploring all you can in Boston, it’ll be time to head back home. Return your car to Logan International Airport and from there fly out to your home airport.

Summary of the 10 Day New England Road Trip Itinerary

• Breakfast at Becky’s Diner | Address: 390 Commercial St, Portland, ME 04101
• Explore Portland Headlight | Address: 1000 Shore Rd, Cape Elizabeth, ME 04107
• Get your history in at Wadsworth Longfellow’s place | Address: 489 Congress St, Portland, ME 04101
• Shop in Old Port and get a snack at the Holy Donut | Address: 177 Commercial St, Portland, ME 04101
• Grab food at the Maine Lobster Shack | Address: 425 Fore St, Portland, ME 04101
• Breakfast at Bayside American Cafe | Address: 98 Portland St Portland ME 04101
• Check out more history at the Victoria Mansion | Address : 109 Danforth St, Portland, ME 04101
• Grab a Mother Clucker at Hot Suppa | Address: 703 Congress St, Portland, ME 04012
• Take the Ferry to Peak’s Island | Address : 56 Commercial Street, Portland, Maine 04101
• Spend your morning experiencing the last of Portland: revisit Old Port, Portland Headlight, or explore the Portland Museum of Art
• Prepare snacks and drive 3 hours to Bar Harbor, where Acadia National Park is located
• Arrive and check into your accommodation in Bar Harbor
• Grab lunner at Galyn’s | Address : 17 Main St, Bar Harbor, ME
• Do some shopping and strolling in Bar Harbor – get some snacks for Acadia
• Get some rest!
• Start early – do a difficult hike on the Beehive Loop Trail or a moderate one on the Bubble Trail
• Eat snacks or your packed lunch at Sand Beach or Echo Beach
• Grab lunch or some popovers and tea at Jordan Pond House | Address : 2928 Park Loop Rd, Seal Harbor, ME 04675
• Drive to Cadillac Mountain and enjoy the views and Thunder Hole to check out the cliffs
• Finish your day in Bar Harbor at the Side Street Cafe | Address: 49 Rodick St, Bar Harbor, ME 04609
• Stop at the Bass Harbor lighthouse then make your 4-hour drive to Portsmouth, NH
• Grab lunch and ice cream – do some walking and shopping in Portsmouth
• Continue your New England road trip to Boston – check into your hotel
• Grab dinner – we got take-out pizza at a corner store and rested from our long drive
• Explore the Freedom Trail by walking to each site (3 miles long, but will take all day)
• Go whale watching at the Stellwagen Bank National Marine Sanctuary
• Explore the Boston Harbor: Charles River Esplanade, Museum of Science, Boston Children’s Museum, or Boston Tea Party Ships and Museum
• Check out the Italian Quarter in the North End
• Grab dessert at Mike’s Pastry | Address: 300 Hanover St, Boston, MA 02113
• Explore the college town of Harvard in Cambridge: Harvard Yard, Harvard Bookstore, Art Museums, Harvard Natural History Museum
• Experience New England candlepin bowling at Sacco’s Bowling Haven | Address: 45 Day St, Somerville, MA 02144
• Check out the iconic Fenway Park where the Red Sox play
• Walkthrough the New England Holocaust Memorial | Address: 98 Union St, Boston, MA 02129
• Grab lunch at the Boston Public Market | Address: 100 Hanover St, Boston, MA 02108
• Revisit Boston Proper – Edgar Allen Poe , and walking ghost tour , picnic in Boston Commons , do more shopping at Faneuil Hall Marketplace
• Grab dinner at the Cheers Restaurant | Address: 84 Beacon St., Boston, MA 02108
• Check out and return home

Map of the 10 Day New England Road Trip Itinerary

Options to Extend Your New England Road Trip Itinerary

If you have more time to spend on a New England road trip, here are a few other historic cities to stop: Concord, Massachusetts, New London, Connecticut, or Providence, Rhode Island.

• Concord, Massachusetts is also full of culture, museums, galleries, and shops. This was also the home to writers such as Emily Dickenson and Henry David Thoreau.
• Providence, Rhode Island is a small city with a lot of history and very friendly people. Be sure to check out the historic downtown area and the amazing restaurants.
• New London, Connecticut where you can visit the U.S Coast Guard Academy, Fort Trumbull State Park, and many more historical landmarks.

What to pack for your 10 Day New England Road Trip

Keep in mind that you’ll be in the car for a few hours, so also pack some comfortable clothes for a long New England road trip.

Boston can also be rainy, so you’ll want to make sure to have a rain jacket and/or water-resistant shoes for all the walking you’ll do.

Here is my recommended list:

• 4-5 tops or shirts
• 1 pair of leggings
• 1 pair of jeans
• 1 jacket (or rain jacket as it does get wet!)
• 1 pair of hiking boots or walking shoes
• 1 pair of sandals
• Sunscreen for Acadia

New England road trip itinerary

When is the best time to go on a 10 day new england road trip.

The best time for a road trip to New England is late spring through early fall. This region of the United States has a temperate climate with moderate temperatures, meaning you can usually avoid extreme heat or cold during these months.

In addition, this time of year offers more daylight hours and plenty of outdoor activities that are perfect for exploring!

You can also plan your road trip to New England during the autumn months, especially in late September to see the foliage change from green to beautiful oranges and reds. Take a drive through the White Mountains in New Hampshire for spectacular views of nature at its finest!

FAQs: 10 Day New England Road Trip Itinerary

Is boston worth visiting.

Absolutely! Boston is full of history and culture. From the Freedom Trail to Fenway Park, there are plenty of places to explore. The food in Boston is also fantastic with a variety of cuisines from Italian in the North End to seafood dishes on the waterfront.

How much money should I budget for a 10 day New England road trip?

It really depends on your budget and what activities you plan to do. For a mid-range budget, a good rule of thumb is to budget around $150-$200 USD per day for food and activities.

Accommodations tend to run between $100-$150 for stays that are close to the areas mentioned in this itinerary. Car rentals range between $80-$90 a day.

If you plan to travel with friends, you can save money by splitting the cost of the car rental and hotels. You can then set your own budget for food and fun activities.

Are there any special precautions I should take when driving in New England?

Yes, some roads can be narrow and winding so it’s important to be aware of the speed limit, road signs, and other drivers. It’s also a good idea to plan your route ahead of time so you know where you’re going.

You might find fog in the northern part of New England as well in the early morning. Be sure to know how to use your fog lights and take it slow.

When in Boston, be prepared for congested traffic, weird roundabouts, and confusing streets (from my own personal experience).

Final Thoughts: 10 Day New England Road Trip Itinerary

That’s a wrap on the ultimate 10 day New England road trip itinerary. New England is a beautiful destination with many historical landmarks, incredible coastal views, and delicious food!

Are you ready to explore New England? Check out these posts!

• 10 Day New England Road Trip (Portland to Boston)
• 3 Day Portland Itinerary
• Best Walking Tours in Portland
• One Day in Camden, Maine
• Boston to Wells Road Trip
• Day Trips from Boston by Train (MBTA Weekend Pass)

Liked what you read? Share it on Pinterest!

My favorite travel tips + resources.

Here is a quick glance at all my go-to travel tips and resources that I use to plan every trip! For more information, check out my travel resources page .

• Booking flights: I use Google Flights to check all routes and find the best flights. Then I compare Skyscanner (for the lowest prices) before I book.
• For hotels, I go through Booking.com or book directly with Marriott (for points + rewards).
• When I travel internationally, I’ll book through Hostelworld for very budget-friendly stays.
• For vacation rentals, use Vrbo or Marriott Homes & Villas .
• Expedia also has some great bundles for hotels, flights, and car rentals altogether.
• Car Rentals: I love renting cars through Discover Cars . They have been consistent and provide the best customer service.
• Trains in Asia: Trip.com has the best options!
• Trains in Europe: Trainline or Omio .
• Visa Application: For a hassle-free process, apply for your visa from iVisa .
• Travel Credit Card: I book all my travel (flights, hotels, car rentals) through Chase Sapphire .
• Vaccines and Medications: Check the CDC website for updates on necessary vaccines to enter a country, including updates on Covid-19 and recommended places to visit. I recommend getting all the vaccines you need before you go!
• Tours + Experiences: I absolutely love my tours! Everything from eerie walking ghost tours to food tours, I’ll usually book something every trip either through Viator or GetYourGuide .
• Entertainment: Looking for entertainment like sporting events, theater shows, or concerts? Book with Ticket Squeeze !
• Tech : Keep your internet browsing safe, secure, and fast with ExpressVPN
• Language Learning: The best place to learn a new language is through Babbel as you travel to countries you don’t know the language.
• What to Pack: I almost always travel by backpack . For products I like, check out my packing guide page for all the things I take with me on different trips.

Pafoua is the author and creator of Her Wanderful World. Pafoua writes from her numerous excursions about all things travel, from fun itineraries to creating memorable experiences on the road. When she’s not traveling, Pafoua loves a fun board game night with her friends or is snuggled up reading a good book. You can find her on Instagram @herwanderfulworld.

• Plan a Road Trip
• Plan a Flight
• Find an Airport
• Where to Stay
• All Questions

Portland (Maine) to Boston drive

Portland (maine) to boston road trip planner.

Here's a sample itinerary for a drive from Portland (Maine) to Boston. If you're planning a road trip to Boston, you can research locations to stop along the way. Make sure you check road conditions to double check the weather. Traveling with a dog or cat? Find pet-friendly stops . Camping along the way? Search for RV campgrounds . Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.

10:00 am  start in Portland (Maine) drive for about 35 minutes

10:35 am   Kennebunkport (Maine) stay for about 1 hour and leave at 11:35 am drive for about 39 minutes

12:14 pm   Portsmouth (New Hampshire) stay for about 1 hour and leave at 1:14 pm drive for about 38 minutes

1:53 pm   Groveland (Massachusetts) stay for about 1 hour and leave at 2:53 pm drive for about 39 minutes

3:32 pm   Salem (Massachusetts) stay for about 1 hour and leave at 4:32 pm drive for about 40 minutes

5:11 pm  arrive in Boston eat at Mike's Pastry stay at The Westin Copley Place

driving ≈ 3 hours

Portland (Maine) to Boston questions

Where should I stop along the way?

Kennebunkport (Maine)   (24 answers)     Wells Beach   (3 mentions)     York Beach   (2 mentions)     restaurants around Kennebunkport (Maine):         All Day Breakfast     questions about Kennebunkport (Maine):         family vacation Portsmouth (New Hampshire)   (21 answers) Groveland (Massachusetts)   (2 answers) Salem (Massachusetts)   (26 answers)     Salem Witch Museum   (2 mentions)     The House of the Seven Gables   (2 mentions)     hotels around Salem (Massachusetts):         Hawthorne Hotel     questions about Salem (Massachusetts):         What is your favorite restaurant in Salem (Massachusetts)?         witch         What is a good nighttime tour

Where's the best place to stay in Boston?

Are you going straight to a hotel, or looking for a vacation rental or Airbnb?

The best resource on neighborhoods, areas, and hotels is the Trippy page on where to stay in Boston .

You can also see most people recommend as the best amount of time to visit. Find out how many days in Boston to stay.

If you're looking for a quick answer, you can check out The Westin Copley Place , which was mentioned 4 times on Trippy.

Here are some more hotels people talk about:

Want to research more popular hotels in Boston? Click the blue button below.

Where's the best place to eat in Boston?

Need some recommendations on somewhere to get food?

Trippy members suggest Mike's Pastry , which was mentioned 15 times.

Here are some more restaurants people talk about:

Want to research more popular restaurants in Boston? Click the blue button below.

What are some things to do in Boston?

This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.

These are some of the places people talk about on Trippy:

Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!

For example, here are some questions people have asked about Boston. Click on any question to see answers from the community!

Click the button below to explore more questions and answers related to Boston.

Do I really have to go back home?

Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!

Want to plan the trip back? Get the reverse directions for a Boston to Portland (Maine) drive , or go to the main page to plan a new road trip .

Looking for ideas for more destinations within driving distance of Portland (Maine)? Try searching for places within 2 hours of Portland (Maine) .

You can also compare the travel time if you're flying or driving by calculating the distance from Portland (Maine) to Boston . Or get a full Portland (Maine) to Boston flight plan .

Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.

And if you know Portland (Maine) well, please help your fellow travelers and answer their questions about Portland (Maine)!

More info on this route:

road conditions

places to eat

cost to drive

cities along the way

flattest route

alternate routes

Google driving directions

12 Photos From Boston To Portland, Maine (Captured On Road Trips)

Your changes have been saved

Email is sent

Email has already been sent

Please verify your email address.

You’ve reached your account maximum for followed topics.

10 Scenic, But Underrated Mountain Towns That Are Great Alternatives To Aspen

10 small towns in the great smoky mountains to visit in winter, 10 small towns to retire in florida, ranked by cost of living.

There's nothing more soothing to the soul than being able to get in your car and having the freedom to drive just about anywhere. Regardless of what the destination is, half the fun lies in all the stops and memories you'll make on the way there. Road trips are based around experience: The sights, sounds, and smells travelers take in along the way are what make it all worth it.When driving from the bustling city of Boston to the calmer, more serene shores (or mountains) of Maine, the sights are half the fun. Whether road-trippers stick to the coast or veers off the beaten path to explore inland, there are bound to be worthy sights that both humble and surprise them. From a busy seaside city to an untamed, mountainous coast, these are all the things to love about the drive from Boston to Maine.

12 As You Leave Boston, Don't Forget To Check Out Its Quieter Parts

One of the best parts of any road trip is that initial first hour. The thrill and excitement of leaving the city will allow travelers to take in the quieter outskirts, and maybe allow some time for the exploration of lesser-seen sights. While it might be familiar, it's still new.

11 Making It All The Way To Bar Harbor Is A Must, Especially For The Salt Life

Bar Harbor is a popular spot in Maine, especially for tourists... But for good reason. This coastal town is stunning and holds all the charm you could ever ask for. Be it a cottage on the water or a hotel with a rooftop balcony, this town is likely to provide all the oceanside serenity you need after leaving Boston.

10 Along The Way, Make Sure To Pull Off For Gorgeous Shots Like This

If you stick to the coast, there will be plenty of chances to pull off and take a moment to enjoy all that the East coast is. The Atlantic waves play a lullaby if you're keen to listen close enough, and the ebb and flow of the waves are enough to quickly de-stress anyone from several hours of driving.

9 Don't Forget About The Food Carts, Like Elotes!

Inevitably, you will get hungry on this awesome road trip. So why not make the food stop a fun one? Sure, there's plenty of rest stops to pull off at and grab some fast-food, but why do that when you can support small? A quick detour into the right small town and you're face to face with comfort food, food carts, and delicious adventures.

8 The Best Stores Are The Ones With A Little Dust On The Shelves

Speaking of making detours, road trips are a great way to plan out all the places you wouldn't normally be able to visit on a day trip. Book stores, for instance, are tiny gold mines in New England. From first and second editions to unique and quirky titles, every one of them is a tiny slice of literary heaven.

7 Acadia National Park Is A Great Way To Unwind From All That Driving

It doesn't require an all-day trip to see the best that Acadia has to offer. One of Maine's best national parks is sure to please any nature-lover, and you also don't need to be a professional in hiking to appreciate the serenity that is Maine's wilderness (although water, solid footwear, and comfy clothes are encouraged).

6 Views Of The Mountains Are Endless Once You Leave The City

The White Mountains through New Hampshire are a sight to be seen, that's for sure. The view of Mount Washington, the tallest peak in New England, rises high above any man-made structure around. This mountain range is likely to grace your line of sight at some point.

5 Mount Washington Is A Bit Off-Course, But Worth It For The Tallest Summit In New England

To get a closer look at the glorious summit, Mount Washington does have an auto toll road that takes visitors all the way to the top. It's seasonal and likely to be crowded, but a bit of pre-planning goes quite a long way when it comes to a breathtaking view from the top.

4 Maine Is Full Of Fun Seaside Towns Just Waiting To Be Explored

Once you get to Maine, there's no end to what can be explored. From the mountains to the beach, you can take your pick of any towns that pique your interest. The scenery is beautiful all over (albeit a bit untamed in some areas), so even walking through the nearest town is likely to be a blast.

3 Don't Forget About The Donuts, New England Is Known For Them

You have to make a donut stop, right? Small bakeries and delis are half the fun of a road trip! While New York claims the best bagels, New England is quite the surprising contender when it comes to all things donut-y delicious. Who knows, you might even discover a new flavor.

2 A Little Stopover In Portsmouth Adds An Air Of Magic To An Otherwise Short Road Trip

The town of Portsmouth, New Hampshire, is a well-kept-secret. With its charming cobblestone streets, you'll feel as though you've stepped through town as you browse boutique shops that aren't too far from the water. With plenty of lunch spots, it can easily become an all-day adventure.

1 Finally, Reward Yourself With An Authentic Lobster Roll... You've Earned It!

So what is Maine known for? Lobster, of course! If taking on a full 10lb hunk of lobster isn't your first choice (cracking claws can be pretty messy), then a lobster roll is a nice and neat way to taste all that New England's best has to offer in terms of fresh seafood.

• Destinations
• Top Sights In Maine

🙌 Awesome, you're subscribed!

Thanks for subscribing! Look out for your first newsletter in your inbox soon!

Get us in your inbox

Sign up to our newsletter for the latest and greatest from your city and beyond

By entering your email address you agree to our Terms of Use and Privacy Policy and consent to receive emails from Time Out about news, events, offers and partner promotions.

Awesome, you're subscribed!

The best things in life are free.

Sign up for our email to enjoy your city without spending a thing (as well as some options when you’re feeling flush).

Déjà vu! We already have this email. Try another?

Love the mag?

Our newsletter hand-delivers the best bits to your inbox. Sign up to unlock our digital magazines and also receive the latest news, events, offers and partner promotions.

• Things to Do
• Food & Drink
• Time Out Market
• Coca-Cola Foodmarks
• Los Angeles

The best destinations for a New England fall road trip

Hop in the car and explore the region in search of changing leaves and find something to do for every type of traveler

Pumpkin spice lovers, rejoice. Fall is finally upon us (well, almost). It’s time to mark your calendars for sighting some proper fall foliage, frolicking in the leaves, and getting lost in a corn maze. While it’s easy to argue that fall is the superior season, not all regions are created equally when it comes to leaf peeping, and it’s no secret that one of the best in the country is in New England. If you’re looking for a proper fall getaway, here are 10 destinations for a New England fall road trip serving up your autumn fix.

RECOMMENDED: The best places to see fall foliage in the U.S.

Been there, done that? Think again, my friend.

New England fall road trip destinations

1.  for hiking: stowe, vermont.

One of the many factors that makes fall so great is the moderate temperatures, which makes September and October a prime time to visit places like Stowe, Vermont. Perched on Mount Mansfield, the highest peak in Vermont, Stowe, is an ideal escape for all of my mountain people. You’ll be situated near Stowe Recreation Path, Stowe Bike Path, and the Stowe Quiet Path, all picturesque trails that are prime for leaf-peeping. For an ideal place to stay, Outbound Stowe has direct access to Stowe’s Recreation Path and is charmingly set next to West Branch Little River. To really drive the mountain factor home, Topnotch Resort is set right at the foot of Mount Mansfield.

2.  For cocktail and beer aficionados: Biddeford, Maine

Often overlooked for its more popular neighbor, Portland, Biddeford, Maine, is one of the best-kept secrets in New England. Beautifully set on the coast, Biddeford provides access to three public beaches: Middle Beach, Fortune’s Rock Beach, and Biddeford Pool. Where Biddeford really shines, however, is its cocktail and brewery scene. Sacred Profrane Brewery and Tanktub offers a selection of craft beers that pair wonderfully with some of their savory menu items, like fish dip with saltines and their “lazy lobster bake.” Lucky Pigeon Brewing Co. has solely gluten-free beers, and Banded Brewing Co. is the town’s designated first brewery. For a cocktail, head to The Lobby Bar located inside The Lincoln Hotel , and for a brunch cocktail, head to Catface Cafe to savor their espresso martini.

3.  For foodies: New Haven, Connecticut

Earlier this year, U.S. Congresswoman Rosa DeLauro boldly claimed New Haven as the pizza capital of the country . While New Yorkers squirmed over the sentiment, it is difficult to argue that New Haven doesn’t make a mean “apizza,” and if you want to plan a New England trip entirely around eating, New Haven is the answer. Frank Pepe Pizzeria Napoletana is known as the best in the city, but Da Legna at Nolo, Ernie’s Pizzeria, Modern Apizza, and Sally’s Apizza shouldn’t be missed either. The city’s culinary offerings go far beyond just apizza (what New Haveners call pizza as a nod to its Neapolitan roots); here, you can get your fix of Greek cuisine at olea , slurp some ramen at Menya-Gumi , and warm up with the flavors of Jamaica at Jammin Jamaican Cuisine.

4.  For the best foliage: Newport, Rhode Island

Let’s be real; whether you are sad that summer is over or simply don’t obsess over autumn as much as the average Tumblr girlies do, fall foliage is undoubtedly a beautiful natural phenomenon. While you can see good foliage in various parts of New England, Newport, Rhode Island, is an underrated gem that is prime for catching those amber-hued trees. Prime time is typically in October, and one of the best places in town for those Insta-worthy fall pics is the 3.5-mile Cliff Walk . From there, you’ll be able to catch sights of both the Atlantic Ocean and the Newport Mansions, which are completely surrounded by leafy trees in shades of red, yellow, and orange.

5.  For one last taste of summer: North Falmouth, Massachusetts

If you’re pining to hang onto summer just a little while longer, nothing will get your fix quite like a New England beach town. And while you might be under the assumption that summer is the only time to visit places like North Falmouth, Massachusetts, fall is arguably better. Not only are the crowds fewer, but you get the treat of enjoying both the crashing waves of Cape Cod and the drop-dead gorgeous foliage. For a resort located right on the water, head to Sea Crest Beach Resort , where you can wake up each day to the salty air and take those therapeutic long walks on the beach as you cry that summer is over. No fake summer is complete without some seafood, so grab some New England Clam Chowder, Haddock & Chips, and, of course, a quintessential New England Lobster Roll from The Hatch.

6.  For small-town rustic charm: Littleton, New Hampshire

Sometimes, we just need a quiet escape, and that’s where rustic American small towns come in. Insert Littleton, New Hampshire. Here, the best plan is to have minimal to no plans. Simply enjoy the relaxed, quaint surroundings of Littleton, which is known as one of the best places in New Hampshire to be fully immersed in the dramatic fall foliage. Grab a bite at Chang Thai Cafe by Chopped contestant Emshika Alberini, and head to Chutters afterward to experience the longest candy counter in the world. One thing’s for sure: you can’t leave town without jumping on the Mount Washington Cog Railway to ride to the top of Mount Washington, the highest peak in the Northeast.

7.  For all things quintessential fall: Burlington, Vermont

Whether it’s sipping cider, attending a pumpkin festival, or going apple picking, autumn is the time for very specific and quirky outdoor activities. And nowhere in New England does it better than Burlington, Vermont. Just an easy train ride away from New York City via Amtrak’s Ethan Allen Express service, Burlington is the place to be for all things fall. Go pumpkin picking, hop on a hayride, and get lost in a corn maze at Sam Mazza's Farm Market or The Great Vermont Corn Maze in Danville . For a real hands-on experience, join the Vermont Pumpkin Chuckin' Festival . For cider-sipping, head to Citizen Cider , Cold Hollow , and VT Cider Lab at the Essex Experience . For a fall-tastic place to stay, Hotel Vermont has just launched a Fall Foliage Hotline. Guests of the hotel can call (802) 651-0080 from September through October, and the Hotel Vermont concierge team will provide insider tips on how to get the most out of viewing Vermont’s foliage.

8.  For your inner child: Kent, Connecticut

Raise your hand if you’re sick of adulting. Club Getaway in Kent, Connecticut is here to feed your inner child and make you forget the stresses that come with, well, being an adult. Sprawled over 300 acres of land, Club Getaway is jam-packed with activities, making for a truly unconventional fall getaway. Whether it’s ziplining, sky cycling, going on a pub hike, playing on giant swings, or perfecting your archery skills, Club Getaway is a safe place to leave your priorities at home and simply be a kid again. Note that Club Getaway closes for the season in mid-October and offers designated dates for fall packages .

9.  For a spectacularly spooky time: Boston, Massachusetts

Salem often gets the gold for the spookiest destination in Massachusetts, but if you want something a little less predictable and more nuanced, Boston is calling. Jump on the Old Town Trolley’s Ghosts and Gravestones tour, where you can take a trolley through various spooky sites, including Boston’s oldest burying grounds, the Omni Parker House (a.k.a. the most haunted hotel in the city), and even walking amongst the dead. You can still certainly get your Salem fix here, too, by jumping on the Salem Ferry , where you can spend a day visiting where witches were burnt at the stake in the 1692 Salem witch trials. You’ll further want to head to Fort Warren, where “the lady in black” (the ghost of the wife of a soldier) is alleged to haunt to this day. For easy access to both the Ghosts and Gravestones tour and the Salem Ferry, make yourself comfortable at Boston Marriott Long Wharf .

10.  For a dog-friendly getaway: Acadia National Park, Maine

Last but certainly not least is one of the most beautiful places in New England year-round: Acadia National Park . Spanning 50,000 acres, Acadia National Park is a great place to be outdoors in the fall and, therefore, a great place to bring your furry best friend. It’s one of the few parks that allows pets, and dogs are welcome as long as they stay leashed. For peak foliage, you’ll want to head here in October. Your accommodation is just as important as the destination you choose, and with a pet, that’s even more so. Terramor Outdoor Resort is deep in the woods, giving you close access to both the park with just two minutes to its entrance. There’s even a designated dog park within the grounds, giving your pup plenty of options to take in one of the most beautiful parts of the Northeast.

[image] [title]

Discover Time Out original video

• Press office
• Investor relations
• Work for Time Out
• Editorial guidelines
• Privacy notice
• Do not sell my information
• Cookie policy
• Accessibility statement
• Terms of use
• Copyright agent
• Modern slavery statement
• Manage cookies
• Advertising

Time Out products

• Time Out Worldwide

Press Herald

Account Subscription: ACTIVE

Questions about your account? Our customer service team can be reached at [email protected] during business hours at (207) 791-6000 .

• Local & State

Portland first responders honor lives lost in 23rd anniversary of 9/11

About 2 dozen Portland residents joined the commemoration at Fort Allen Park on Wednesday morning.

You are able to gift 5 more articles this month.

Anyone can access the link you share with no account required. Learn more .

With a Press Herald subscription, you can gift 5 articles each month.

It looks like you do not have any active subscriptions. To get one, go to the subscriptions page .

Loading....

On the first anniversary of the Sept. 11 terrorist attacks, Gregory Gay left work in Portland about 5 p.m. and drove to New York City to see ground zero.

He spent the night walking around, meeting and exchanging hugs with others who had come out to mark the somber occasion. About 6 a.m. the next day, he met a Port Authority police officer outside of the Millennium Hotel. The company he worked for, United Rentals, had donated its equipment to the city after the tragedy. The officer then walked with him into the site and to the Hudson River, where the victims’ families were, he said.

He wasn’t sure what compelled him to make the trip.

“I don’t know,” said Gay, now 67 and a Marine Corps veteran. “I think we all have a connection in some way.”

Twenty-two years later, Gay pulled on his Boston sweatshirt and joined about two dozen other Portland residents for the city’s ceremony at Fort Allen Park commemorating the 23rd anniversary of the attacks on the Pentagon and the World Trade Center.

Portland police officers and firefighters stood in formation as fire Chief Keith Gautreau and police Chief Mark Dubois were escorted by a bagpiper to lay two wreaths next to the memorial, which reads, “All gave some, some gave all, and all still some give.” Advertisement

“I ask you all this morning, especially my fellow first responders here today, across the country and especially after last night’s debate, let us put our political and social differences aside for at least this day to honor those lost and keep our promise to never forget,” Gautreau said.

Portland fire Chief Keith Gautreau, center, salutes the 9/11 memorial after laying a wreath in Fort Allen Park on Wednesday. Brianna Soukup/Staff Photographer

Wednesday’s clear, bright sky was reminiscent of that Tuesday in 2001, when nearly 3,000 people died in New York City, Washington, D.C., and Pennsylvania, Gautreau said. Among those killed were the brave New York City firefighters, police officers and Port Authority officers who ran toward the towers “without hesitation,” he said.

Gautreau reminded the small crowd of the community’s close connection to the attacks – two of the men who would later hijack American Airlines Flight 11 and destroy the World Trade Center flew out of the Portland International Jetport in the early morning. The plane left Boston and and crashed into the North Tower at 8:46 a.m. Mohamed Atta, of Egypt, and Abdulaziz al-Omari, of Saudi Arabia, stayed in South Portland the night before, at the Comfort Inn on Maine Mall Road in South Portland.

20 years later, they’re haunted by their encounters with 9/11 hijackers

Gay said he knows and respects a lot of Portland’s first responders. Since 9/11, their loved ones worry even more if they will come home safely, he said.

After the ceremony, he quietly stood in front of the memorial. On the same hand that was holding his coffee, he wore a bracelet representing each of the Armed Forces.

“These guys do a lot for us,” Gay said. “A lot of people don’t realize that. Not only them, but it takes a toll on their families more than anything.” Advertisement

On that trip to New York 22 years ago, Gay remembers having someone take his photo. He had just pulled out a photo from his pocket of his friend’s son, who was born at 4 a.m. on Sept. 11, 2001.

“With death comes life, no matter how you look at it,” he said to the stranger.

Today, Gay still holds onto a little urn filled with dirt and glass he collected from ground zero.

“I might just bring it to the headquarters of the fire department and leave it with them because I don’t have any family or anybody to leave it to,” Gay said. “I figured it’d be a nice little gesture.”

Related Headlines

20 years later, they’re haunted by their encounters with 9/11 hijackers

9/11 anniversary brings Biden, Harris and Trump together at ground zero

Comments are not available on this story.

Send questions/comments to the editors.

Maine issues its first-ever recall of tainted recreational marijuana

State’s highest court favors ‘squatter’s rights’ in old orchard beach parking dispute, the wrap: anjon’s set to reopen next week; union bagel moves to falmouth, developers pitch second condo complex with accessory dwelling units in portland, portland geese deformed by ‘unnaturally high-calorie diet’, member log in.

Please enter your username and password below. Already a subscriber but don't have one? Click here .

Not a subscriber? Click here to see your options