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.

The drive from Boston to Portland is very scenic, especially once you get to the Maine coastline.

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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.

Spring Point Ledge Lighthouse is one of the best things to see when driving Boston to Portland, Maine.

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)

While driving Boston to Portland, Maine, you'll see so many great spots to take photos, including this buoy wall in Rockport, MA.

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.

Driving Boston to Portland, Maine allows you to stop in some of the best coastal New England towns. This one is Rockport, MA.

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.

Portsmouth is a great stop to make when driving Boston to Portland, Maine, and is home to some really nice restaurants and shops.

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!

Kittery, ME offers a variety of things to do when stopping during your drive from Boston to Portland, Maine.

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.

Nubble Lighthouse is one of the best sites to see when driving Boston to Portland, 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.

Ogunquit is one of the best places in Maine if you're looking to spend time at one of the best beaches in the state.

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.

Views from downtown Kennebunkport near Dock Square are really serene, and this is one of the best places to stop during the drive.

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.

The pier at Old Orchard Beach in Maine is one of the more unique places to stop when driving Boston to Portland, Maine.

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).

Portland Head Lighthouse is an absolute must when driving Boston to Portland, Maine.

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, rthe community already has plans to rebuild them. I’m closing monitoring this, and will. update as soon as I have more information, but it will likely take at least a year, but likely longer.

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.

The Cottages at Cabot Cove is my favorite place to spend the night when driving Boston to Portland, Maine.

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

If you stay at the Cottages at Cabot Cove, definitely take their rowboats out into the cove. This was from a trip at the end of October, and the foliage was magical.

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.

Spring Point Ledge Lighthouse in Cape Elizabeth is a really fun 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.

Taking a walk along the beaches in Kennebunkport is one of the most fun things to do if you stop in this area during the trip.

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

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!

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This beautiful mural in Newburyport can be found close to Market Square.

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Boston to Portland, Maine: A Road Trip Itinerary (2023-2024)

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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!

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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).

A statue of iconic Bewitched actress on a crescent moon with broom sits visible on one of the best tours in Salem, Massachusetts.

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 ! 

Witch house in Salem

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)

A boat dock with colorful boats and buildings, and fall trees reflected in the water

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. 

A store front with colorful shirts on display and a sign saying "Good Vibes Only" out front

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)

Long sandy beach stretches near the ocean. There's a strip attached covered in hotels, buildings, shops, and more.

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)

Town sitting on the edge of a lake under a sunset with cotton candy skies.

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!

Red sign on a red building that says "Strawbery Banke Museum"

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)

White Nubble Lighhouse and lightkeepers house are visible on a grassy island, with blue skies over head and the ocean in front with waves crashing against the rocks

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)

Ogunquit Harbor full of boats on a sunny day in things to do in Ogunquit

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)

Large yellow and white mansion on a fall day with a carpet of leaves on the ground

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! 

Colorful flowers in front of canal and large grey house

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)

A pier is seen jutting out into the ocean with a sandy beach extending out beside it; a beachfront amuseument park and the surrounding town is silhouetted by the setting sun

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)

Black and white lighthouse on a rocky cliff near the water under a blue sky.

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)

historic downtown district in portland

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.

The Portland Observatory is a red brick tower with a 360 observation deck that allows for views of Portsmouth and the ocean beyond

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

Portland, Maine, USA coastal townscape

Road Trip From Boston To Portland, Maine

If you don't think a short drive could match up to a cross-county adventure, the road trip from Boston to Portland is bound to change your mind - featuring some of the East Coast's most beautiful beaches and cities, this is a trip you're bound to remember for a long time.

The 110-mile road trip from Boston to Portland takes 1 hour 45 minutes to drive. Stops along 2 different routes include Bear Brook and Hampton Beach State Parks, Old Orchard Beach Pier, Canobie Lake Park, Salisbury Beach State Reservation, and Salem.

Be sure to keep on reading to learn all the details regarding this beautiful itinerary.

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

The road trip from Boston to Portland covers 110 miles of ground along the quicker route and takes around 1 hour 45 minutes to drive. With a drive this short, you can take off at virtually any hour and make it to Portland in time to do something fun in Portland.

With that said, a better way to enjoy this route is to make as many stops as possible along the way - the route is packed with Atlantic Coast attractions for you to check out, and there are plenty of inland detours you may want to consider too.

Portland Head Light in Maine at sunset with pink clouds in the sky

Another way of approaching the drive is to start off your adventure inland, driving to Manchester in New Hampshire before returning to the coast for the other half of the journey. This route takes a bit longer to drive, coming in at 140 miles and taking 2 hours 10 minutes to drive.

Whichever route you choose, you can expect a fair bit of traffic on your way out of Boston and into Portland - if you happen to get caught up in congestion, you can always slow down and check out some of the gorgeous beaches and resort towns on the Atlantic Coast.

If you are looking to extend your road trip, here is our guide for the ultimate Maine road trip itinerary:

READ MORE - Ultimate Maine Road Trip Itinerary

Best road trip route from Boston to Portland

There is no best route for the road trip from Boston to Portland - the main difference is that the longer route goes a bit inland, passing cities and parks that, if you're short on time, might be too out of the way for a detour when taking the coastal route.

Whichever way you spin it, it won't take more than four hours to drive to Portland and back, so consider taking one route on the way there and the other during the return trip.

The Coastal Route

Leave Boston via Interstate 93, cutting through Middlesex Fells Reservation before hopping onto Route 95. Pass Breakheart Reservation and Lynn Woods, and take the time to drive to Salem and check out the Salem Witch Museum.

Back on the interstate, pass Bradley Palmer State Park before cutting through Georgetown-Rowley State Forest and crossing the Merrimack River. Then, be sure to visit Salisbury Beach State Reservation, North Beach, and Hampton Beach State Park before reaching Portsmouth.

Cross the Piscataqua River to enter Maine, then stop by Rachel Carson National Wildlife Refuge before taking a break in Biddeford. Finally, stop by Scarborough Fair State Park before getting onto Interstate 295 and reaching Portland.

Waves in the Atlantic Ocean and houses on cliffs in York, Maine.

The Inland Route

Once again, take Interstate 93 out of Boston, but after cutting through Middlesex Fells Reservation, stay on this interstate and pass Harold Parker State Forest and the town of Andover.

From Lawrence, you can do some optional detours to Haverhill or Lowell, then pass by Canobie Lake Park and detour to America's Stonehenge before taking a break in Derry.

Next up is Manchester - explore the city and get on Route 101, passing Bear Brook and Pawtuckaway State Parks. From Exeter, simply follow the route to Interstate 95 - the two routes converge just south of Portsmouth.

Looking to stay longer in Maine? Here is our guide to the ultimate road trip itinerary in Maine .

Best places to stop between Boston and Portland

The road trip from Boston to Portland is filled with amazing hotels, and although there's not a lot of driving, many of the beaches and towns along the way deserve at least a full day's attention. These are some of the hotels you'll want to book before taking off:

Admire the riverside view in Portsmouth

Home to some of the most gorgeous architecture along the East Coast, Portsmouth is a city brimming with charm and personality. The best resort in town is The Hotel Portsmouth, whose elegant rooms will leave you feeling like 17th-century royalty .

Nothing can beat a cozy weekend morning by the fireplace with a good book, and for good measure, the hotel also throws in some amazing window views of the exterior, which is as lovely as they come.

Gardens at Prescott Park, in Portsmouth, New Hampshire

The real draw of this resort is the location, though - situated in Haymarket Square, this place is a stone's throw from many of Portsmouth's finest attractions, including The Strawberry Banke Museum and Prescott Park.

Best of all, the Piscataque River is mere minutes away on foot, so if you want to make the most of the city, take a leisurely stroll along the riverbank and enjoy the view of a lifetime.

The price is extremely fair for hotel in a major tourist thoroughfare, and taken together with the elegance of the interior and the resort's proximity to all things Portsmouth, you have an offer that can't be beat.

Take in the beauty of The Portland Waterfront

As one of the swankiest cities in all of Maine, Portland is the kind of place that keeps you coming back for more every tourist season. You'll want to spend a long time here, ideally in Portland Harbor Hotel, the epitome of style, comfort, and oceanside luxury .

After a few minutes of relaxing in your cozy room or in the tastefully decorated lobby, you're guaranteed to fall in love with every nook and cranny of this fabulous resort.

Historical Portland Old Port after sunset

For a meal that can't be beat, head out to the hotel's very own BlueFin North Atlantic Seafood Restaurant to enjoy some of the finest seafood you're likely to try.

Once you're done, you can hit the fitness center before retreating to the comfort of your suite's spa bath for that final touch of elegance before going to bed.

Portland is one of the most historically significant cities in all of Maine, and luckily, the Portland Harbor Hotel is mere minutes from various historic districts and monuments.

Things to see on a road trip from Boston to Portland

As short as the drive is, the road trip from Boston to Portland can keep you occupied for days on end. If you have the time, try to devote at least a week to this trip to see as much as you possibly can.

The route is more diverse than the short mileage might have you believe, so it's hard to list every attraction on the way, but these are some of the absolute highlights:

  • Salem Witch Museum - Located in Salem, this museum lets you see historically accurate reenactments of 17th-century witch trials.
  • The Witch House - Although it doesn't delve in reenactments, this house is claimed to be an actual site for witchcraft over 300 years ago.
  • The House of the Seven Gables - New England's oldest wooden mansion that also served as inspiration for a chilling Hawthorne novel.
  • Singing Beach - Located in Manchester-by-the-Sea, this beach is one of the best places to experience an East Coast summer.
  • 7 Seas Whale Watch - Located just a short distance away from the Singing Beach, this place offers a surreal whale and dolphin-watching experience.
  • Castle Hill on the Crane Estate - Palatial English-style mansion that is perfect for a photo session.
  • Salisbury Beach State Reservation - For an unparalleled beach experience, enjoy the crashing of the waves at Salisbury Beach as you take a stroll along the boardwalk.
  • Hampton Beach State Park - Undoubtedly one of the best beaches in the northeast, Hampton Beach State Park deserves as much attention during this trip as Portland itself.
  • Odiorne Point State Park - Well over 100 acres of trails with amazing ocean views along the rocky Atlantic shoreline.
  • Strawbery Banke Museum - This iconic outdoor museum will give you a clear perspective on old-time living in New Hampshire.
  • Funtown Splashtown USA - You can unleash your inner child in Maine's largest water and amusement park - your kids are guaranteed to get a kick out of this place too!
  • Canobie Lake Park - An iconic theme park housing some of the most thrilling rides in all of the States.
  • America's Stonehenge - This beautiful archaeological site is surrounded by incredibly scenic hiking trails shrouded in greenery.
  • Manchester (New Hampshire) - Art lovers will get a kick out of the innumerable museums and art exhibits that call this place home.
  • Bear Brook and Pawtuckaway State Parks - Taken together, these two parks offer some of the most unforgettable vistas and hiking trails in New Hampshire.

Bridge and pine trees at Bear Brook State Park, New Hampshire

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

There really is no wrong time to do the road trip from Boston to Portland, although as you might expect from a coastal trip, the warmer seasons are generally the safest options.

Since you'll be passing many parks and beaches on the way, you'll want to take full advantage of the East Coast sunshine by traveling in the summertime - places like Hampton Beach State Park really come alive this time of year.

Aerial view of the Portland Observatory in Portland, Maine

The same is true for Portland itself, whose peak tourist season is around July and August. With temperatures peaking at around the mid-to-high 70s, Portland is extremely pleasant in the summer if you don't mind the crowds.

The city's temperatures take a bit of a hit in the fall, which can be good news if you're traveling on a budget - the only visitors you can find here in October and November are food festival attendees, so you can get an amazing deal on a hotel room around this time.

Winters in Portland can be harsh if you're not accustomed to temperatures in the 30s, and it takes a while for spring to actually kick in. With that said, the city looks divine once the snow has melted and the greenery starts to bloom again.

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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 .

boston to portland maine road trip

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.

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Guided by Destiny

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

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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.

Fall New England road trip stop in New Hampshire

Table of Contents

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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.

The Witch House Salem Massachusetts

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.

The Witch House in Salem Massachusetts

  • 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 .

Boutique shops in Salem Massachusetts

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.

Fall on the coast in Portland Maine

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.

Bard Coffee cappuccino in Portland Maine

  • 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.)

The Holy Donut 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!

Portland Maine Head Light

  • 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!

cocktail from Lukes Lobster in Portland Maine

  • 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.

Oxbow Blending and Bottling flight

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.

Kancamagus Highway during fall New England road trip

  • 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.

Albany Covered Bridge in New Hampshire in the fall

  • 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.

Dinner at The Common Man in Lincoln New Hampshire

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!

Percy Farm Corn Maze in Waterbury Vermont

  • 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!

Cold Hollow Cider Mill cider and donut

  • 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.

Church Street Marketplace in Vermont

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).

Molly's restaurant, one of the stops on the New England road trip itinerary

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.

Inside of the Boston Public Library, one of the most iconic things to do in Boston

  • 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!).

Speakeasy in Cambridge, A4cade

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!

VERSUS bar in Boston

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

Citrus and Salt restaurant in Boston dining area

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

Terra Eataly Boston dining area

  • 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.

Stuffed whole lobster from Legal Sea Food in 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!

Cappuccino from Trident Bookstore in Boston

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!

Fall Road Trip New England

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.

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

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Sidewalk Safari | Part-time Travel Blog

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

Boston to Maine Road Trip: Potts Point Maine

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.

Things to do in Maine in the summer: Turkeys at Maine Audobon's Gilsland Farm near Portland

Maine's Craft Beer Scene

"Beauty is in the eye of the beerholder"

Craft beer and kettle corn in Portland Maine

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.

Maine Getaway: plovers at Potts Point

New England Road Trip Stop #15: Bath, Maine

Where to stay on a boston to maine road trip.

Where to stay in Maine: Benjamin F. Packard Bed and Breakfast's Bergamesco sheep dog

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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.

boston to portland maine road trip

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

Boston skyline and harbor

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.

George Washington statue

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.

Salem, Massachusetts

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

North church Market Square

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.

Memorial bridge

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

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

Ogunquit

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.

Ogunquit beach

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

Kennebunkport sign

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).

Kennebunkport main road

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.

Batson River brewing

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.

Old Orchard beach

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.

Old Orchard Beach amusement park on the beach

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.

The view from the top of Mount Battie

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.

Portland head light

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.

Hardshore Distilling company

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

Luke's Lobster

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!)

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Laura

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.

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Your Guide to Wandering

Portland Head Lighthouse is a must-see on your roadtrip

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!

Boston Public Gardens

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!

Visit Salem's Witch Trial memorial

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!

Plum Island has salt marshes and dunes

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 Maine is a charming fishing town

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 Maine is a cute stop on your road trip.

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.

The pier at Old Orchard beach is a must see for its old-fashioned carnival feel

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.  

The portland area has several light houses

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. 

Downtown Portland Maine

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.

Amtrack map from Boston to Portland

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.

Coastal Maine is a must-visit trip

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!

Lobster rolls and lighthouses: The perfect Maine road trip

Andrew Collins

Maine's breathtaking coastline is unlike any other. It's only about 280 miles from the New Hampshire border to the New Brunswick, Canada, border if you follow the region's principal road, U.S. Route 1 (along with state Route 189 for the final stretch).

However, this jagged shoreline is anything but a straight shot. And if you measure the tide coastline — which includes every peninsula, inlet, island and tidal basin — the Maine coast actually measures 3,478 miles, making it the fourth-longest in the country (it slightly exceeds California's).

You could drive it sticking closely to U.S. 1 in about seven or eight hours, but you wouldn't actually see much of the ocean. For views of Maine's azure waters — its rocky headlands dotted with imposing historic lighthouses, its sheltered harbors aglow with sleek sailboats and colorful lobster buoys — you'll want to detour frequently from the main route. To fully experience this breathtaking maritime landscape immortalized in the paintings of Winslow Homer, Marsden Hartley, Andrew Wyeth and countless other luminaries, spend at least a few days (or ideally a couple of weeks) tracing the coast's many contours.

boston to portland maine road trip

As you traverse the coast in a northeasterly direction, heading "down east" as it's known in Maine vernacular, you'll encounter far fewer people and much less commercial development. The relatively direct stretch from the New Hampshire border to the state's largest city, Portland, abounds with sophisticated sea-to-table restaurants and posh country inns as well as charming lobster shacks, enticing ice cream stands and nostalgic minigolf centers. Once you get past Freeport, with its iconic L.L. Bean flagship store, you start to encounter the wilder and more rugged Maine coast, with its long and narrow peninsulas.

Along this part of the coast, you'll still find pockets of upscale vacationers in affluent summer colonies like Boothbay Harbor, Camden and Bar Harbor, but the pace slows. The final stretch of coast beyond Mount Desert Island to the Canadian border feels completely rural. You'll encounter few fellow travelers in this sparsely populated but verdant area that depends economically more on commercial fishing and blueberry farming than tourism.

But by exploring the full length of Maine's gorgeous coast, you'll find much to appreciate. You can feast on incredible seafood (not just lobster but rock and Jonah crab, oysters, mussels, and myriad fish) and a dizzying variety of craft beers. You'll discover superb art museums and galleries, and diverse flora and fauna to view on coastal hikes, wildlife-watching cruises and kayaking and biking tours. And, of course, there's the stunning natural scenery of Acadia National Park.

Here's your guide to planning the perfect coastal Maine road trip and everything you should see and do along the way.

Maine road trip planning

boston to portland maine road trip

GPS devices tend to be at cross purposes with actually enjoying a drive up the Maine coast, as they constantly attempt to shunt you onto U.S. Route 1 or, worse, Interstate Highway 95, instead of the happily meandering and circuitous roads that run closer to the shoreline. Unless you're pressed for time, feel free to ignore the entreaties of your GPS and take the scenic route whenever possible. Detour down to the tips of Maine's finger-shaped peninsulas, and if there's an island you can reach by bridge or even by ferry, go for it, at least once. Bailey Island, Deer Isle and Vinalhaven (which entails a ferry ride) are all good bets.

Note that many municipal beaches have steep parking fees for nonresidents, sometimes $25 or more. Day-use fees at state beaches are per person rather than per vehicle and typically cost around $7 or $8 per person. In Portland and some of the more popular small towns along the coast — Bar Harbor, Kennebunkport, Ogunquit — street parking can be hard to come by, especially during the summer high season, so prepare to use a pay lot that may also be expensive.

Gas stations are present all along U.S. Route 1 and in most towns, but they can be harder to find, or a lot more expensive, on the more rural peninsulas and islands. It's best to top off your tank before venturing anywhere remote.

Set aside enough time

boston to portland maine road trip

If you're driving this full itinerary from Kittery to the Canadian border, give yourself a minimum of five days and four nights to be able to experience the key sights along the way. This allows you to set aside a full day each for exploring Portland and Acadia National Park, and enough time to drive through all of the towns described in this article. To appreciate this trip at a more leisurely pace, budget a week to 10 days and try to spend two nights in some of the more prominent areas, such as Kittery-Portsmouth, Portland, Rockland-Camden, and Bar Harbor-Acadia National Park. If you have two weeks or even longer, you won't run out of engaging things to see and do.

Getting to the Maine coast

Boston Logan International Airport (BOS) has by far the greatest number of direct flights in New England, and it's just a 75-minute drive from the Maine border. Another option is to fly into Maine's small, user-friendly Portland International Jetport (PWM), which is a 45-minute drive from Kittery. A lesser-known option that's just a 50-minute drive from Kittery is Manchester-Boston Regional Airport (MHT) in New Hampshire. It's served by several of the major airlines. Although Logan Airport is likely the easiest to reach from much of the country and many international destinations, it is a busy hub in a city with notorious traffic, and rental car rates tend to be steeper than at the airports in Portland and Manchester, which are also smaller and more pleasant to navigate.

From Boston, Amtrak serves Portland and several smaller towns along the lower Maine coast. And there's frequent daily bus service on multiple carriers from Logan Airport and downtown Boston to both Portsmouth and Portland.

Best starting and end points on the Maine coast

boston to portland maine road trip

This itinerary follows Maine's coast in a northeasterly direction, beginning at the town of Kittery, which is just across the Piscataqua River from Portsmouth, New Hampshire. This corner of the state is easy to get to, as it's just a 75-minute drive up the coast from Boston via I-95, and there are plenty of hotels in the area, both on the New Hampshire and Maine sides of the border. This trip ends at the Canadian border, where you have the option of extending your adventure by continuing into New Brunswick and potentially beyond. Although it can take several days to travel along the coast's meandering roads, exploring its peninsulas and inlets, the drive back from Lubec to Kittery-Portsmouth takes just under five hours if you take the most direct interior route (state Route 189, U.S. Route 1, state Route 192 and state Route 9 to Bangor, and then I-95 the rest of the way).

The best time to visit the Maine coast

boston to portland maine road trip

For the best balance of weather and scenery without excessive crowds or super-steep hotel rates, make this trip during the spring and fall shoulder seasons, between May and mid-June or mid-September and mid-November. The exception to this rule is fall's peak foliage season, which along the Maine coast is generally from around mid-September through the first week of November. Although the coast attracts fewer leaf-peepers than interior New England, crowds do pick up around this time and hotel rates can also spike a bit.

July and August are peak high-season, as are holiday weekends in spring and fall. This is the best time to laze on Maine's beaches and even swim in the ocean (which is still pretty chilly, with highs averaging around 70 degrees in summer). It's also when seasonal businesses like lobster shacks, ice cream stands and scenic tour boats have their longest hours. But you'll pay a premium at coastal hotels during this time (note that the starting rates for hotels recommended in this article are for the summer high season).

Conversely, winter on the Maine coast can be a bargain as long as you don't mind bundling up, and you'll sometimes have beaches all to yourself. But many businesses, including lodgings and restaurants, shut down in winter — and in some cases all the way from mid-October through early May, especially the farther up the coast you go.

Kittery to the Kennebunks

boston to portland maine road trip

More than any other section of Maine's coast, this relatively short (30-mile) stretch in the state's southwestern corner is easiest to access from coastal roads, which more or less parallel the shore's contours, even beyond Kennebunkport and up through Cape Elizabeth and South Portland.

The region is characterized by broad, crescent-shaped, golden beaches and is home to the greatest concentration of tourism-related businesses. You'll find no shortage of accommodations, from swanky seaside inns to low-frills, family-friendly motels to vacation rentals of every configuration and price range. Although the population swells in summer and traffic can slow to a crawl on weekends, don't give in to the temptation to skip this region in favor of the quieter areas beyond Portland. It's a beautiful part of the state with a number of appealing attractions. What you might consider doing, however, is timing your trip so that you're in this area midweek rather than during the busier weekend.

Kittery and the Yorks

Start your journey by taking U.S. Route 1 over the Memorial Bridge, which crosses the Piscataqua River from historic downtown Portsmouth, New Hampshire, to Kittery, Maine's oldest town. If you want to fuel up early, stop on Badger's Island, which is right in the middle of the river, for a hearty meal at Ore Nell's Barbecue or in the historic downtown at Lil's Cafe , an artisan bakery with great coffee drinks.

Continue east on state Route 103 along the curving riverfront rather than following U.S. Route 1 into the tangle of outlet shops for which Kittery is most famous. Stop to walk around colonial-era Fort McClary State Historic Site , with its formidable granite walls and views of pretty Portsmouth Harbor. The road curves past characteristic colonial homes before joining with U.S. Route 1A, a scenic coastal road that passes through the classic seaside vacation villages of York Harbor, York Beach and Cape Neddick. These towns have a nostalgic family vacation vibe and there are plenty of places to hop out for a stroll along the sand or a bite to eat overlooking the sea.

Just north of York Beach — a stretch of beach cottages and hotels that looks like a postcard from the 1940s — turn right (follow the signs) to the parking area for what's quite possibly the most photographed building in Maine: Nubble Lighthouse, an elegantly simple white tower beside a red-roofed Victorian keeper's house set on a small rocky island just offshore. You can't actually visit the island, but the view from across the water is splendid, and next to the parking lot, Fox's Lobster House is a good spot to indulge in your first bowl of chowder or lobster roll.

Optional side trip to Portsmouth, New Hampshire

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The largest community on New Hampshire's 18-mile shoreline, this upbeat historic city with a population of around 23,000 is both an excellent base for exploring the adjacent southwestern corner of Maine and a delightful destination in its own right.

A compact seaport, Portsmouth is known for its carefully preserved colonial buildings, many of them open to the public. A highlight is Strawbery Banke Museum , a 10-acre living history village of more than three dozen restored structures. Sometimes described as a miniature Portland, this city of narrow tree-shaded lanes and well-tended gardens has a growing restaurant scene and plenty of galleries, crafts shops, bookstores and clothiers to keep you busy.

Just north of Cape Neddick, where U.S. Route 1A cuts west to join U.S. Route 1, turn right onto Shore Road and follow this narrow, curvy route into charming Ogunquit, which developed into an artists colony and a summer resort in the late 19th century and has in more recent decades become a popular LGBTQIA+ destination. Testament to this cheerful beach town's creative legacy are the small but excellent Ogunquit Museum of American Art and the acclaimed Ogunquit Playhouse summer theater. Be sure to check out the shops and seafood eateries (such as Footbridge Lobster and Barnacle Billy's ) of Perkins Cove, where there's also a photogenic footbridge across the town's boat basin. From here, walk the stunning 1.3-mile Marginal Way footpath along a series of sea cliffs into the cute downtown, where you'll discover a number of hip bars and restaurants.

Kennebunkport

As you head north on U.S. Route 1 from Ogunquit, turn right onto the state Route 9 shore route into the old-money enclave of Kennebunkport, with its appealing village center bisected by the scenic Kennebunk River. Stroll among Dock Square's many shops and restaurants, where you can also book a sightseeing cruise on The Pineapple Ketch , a historic 38-foot ship that provides a glimpse of the many imposing summer cottages (mansions, really) that dot the town's shoreline, including Walker's Point, aka the Bush compound, which served as the "Summer White House" for President George H.W. Bush. Off Dyke Road a few miles northeast of town, Goose Rocks Beach is one of the area's gems, offering great opportunities for tidepooling and soaking up rays.

Where to stay

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With days of driving ahead, you might consider treating yourself to a night or two in a fabulous spa resort, like Cape Neddick's sumptuous Cliff House Maine (rates start at $699 per night), which is perched on a dramatic rocky ledge a few miles south of the Ogunquit border. In addition to having a 9,000-square-foot spa overlooking the sea, this contemporary 226-room hotel boasts a championship golf course, several restaurants and myriad recreational activities. From the enchanting Trellis House (rates start at $309 per night), an eight-room bed-and-breakfast surrounded by lush gardens and greenery, you're steps from Ogunquit's Marginal Way coastal path and within walking or trolleying distance of the beach and local dining.

The contemporary-chic AWOL Kennebunkport (rates start at $327 per night) offers a distinct contrast to the area's many old-fashioned inns. A short walk from lively Dock Square in Kennebunkport, it's made up of 17 airy cabins with low-slung, tasteful furnishings and private patios and balconies. Most rooms have fireplaces, and rates include a breakfast featuring a toast bar with bagels, muffins, breads and gourmet toppings. AWOL is part of the renowned boutique hotel brand Lark Hotels, which has four other Maine properties, including the stunning Kennebunkport Captains Collection (rates start at $471 per night), which is just around the corner and consists of four smartly updated historic homes with plush rooms and suites outfitted with soaking tubs, working fireplaces and plenty of other perks.

Just across the state line in Portsmouth, you'll find a great selection of both modern full-service hotels and distinctive urban inns. A couple of notables include the Hotel Thaxter (rates start at $369), a new 15-room boutique inn within the heart of the city's historic downtown, and Wentworth by the Sea (rates start at $389 per night), which is a 10-minute drive outside of town on the beautiful New Castle island. This legendary grande dame was built in 1874 and overlooks a scenic harbor where the Piscataqua River meets the ocean. It offers a spa, two pools, tennis courts and a Scottish-style links golf course.

Greater Portland

boston to portland maine road trip

Maine's largest city has just under 70,000 residents and is 50 miles up the coast from the New Hampshire border. In addition to being a picturesque port city with an incredible food scene, it's an excellent place to anchor yourself if you're planning a longer stay and appreciate having proximity to both the sea and a vibrant arts and cultural scene. From Kennebunkport, state Route 9 leads into the towns that form the metro area's southern edge, including Biddeford and South Portland.

Biddeford and Cape Elizabeth

From Kennebunkport, follow Route 9 as it curves back inland along the Saco River into Biddeford, a once-thriving textile mill town that underwent a severe downturn during the second half of the 20th century as industry moved elsewhere. By the early 2000s, the city center's handsome, though largely empty, redbrick mill buildings and storefronts began to attract chefs, brewers, makers, artists and other entrepreneurs, and today Biddeford buzzes with activity.

Stop for breakfast or lunch at acclaimed spots like Catface Cafe and the Palace Diner , or a memorable dinner at Elda . Sample fine spirits, including aromatic small-batch gins, at cozy Round Turn Distilling , and house-roasted coffees and local beer at the inviting bookstore-cum-cafe Elements .

Once you've filled up on excellent food and drink, follow U.S. Route 1 over the river into another small industrial city, Saco. Here, you have a decision to make about which route to follow. If you have a soft spot for the thrum of boardwalk amusement parks, fried-dough and saltwater taffy vendors, T-shirt shops and souvenir stands, and other retro-kitschy fun, head east a few miles to Old Orchard Beach, a spirited if at times raucous honky-tonk vacation town with a long pier, a beach that's jammed on weekends with towels and umbrellas, and fireworks shows on Thursday nights from late July through early September.

If this isn't your bag, continue up U.S. Route 1 to the bedroom community of Scarborough, and take state routes 207 and 77 through the upscale seaside town of Cape Elizabeth. On this scenic route, you can detour south to Prouts Neck to visit the Winslow Homer Studio ( tours are offered only by advance reservation through the Portland Museum of Art), where the artist painted many of his legendary Maine seascapes from the 1880s until his death in 1910. And you can visit the Portland Head Light , which has served as a beacon to ship captains since 1791 and inspired countless paintings, including Edward Hopper's memorable 1927 work, "Portland Head." You can walk around this graceful stone tower and tour the museum inside the quaint keeper's house — walking paths lead along the rock bluffs and throughout surrounding Fort Williams Park. Route 77 continues north across Casco Bay Bridge and into the heart of Portland.

boston to portland maine road trip

With its walkable streets lined with stellar restaurants, cocktail lounges, fine galleries and fashionable boutiques, Portland is the perfect city to ditch your car for an afternoon, or even a few days, and explore on foot. The exercise will come in handy given how much eating and drinking you'll be tempted to indulge in. Moreover, there's a clutch of first-rate hotels downtown.

Great views can be had from the grassy lawns of the Western Promenade and Eastern Promenade, two hilltop parks that bracket the city. The Portland Museum of Art features extensive holdings of painters who have immortalized the region's natural scenery, including Homer and Hopper but also John Marin, George Bellows and Andrew Wyeth. There's also an outstanding contemporary collection and terrific rotating exhibits. A few blocks away you can visit the childhood home of poet Henry Wadsworth Longfellow, which now contains the Maine Historical Society . Nearby, the Old Port district exudes old-world charm with its bustling wharves, seafood markets and narrow lanes.

Where to eat and imbibe? Longtime favorites include Fore Street for locally sourced seafood and meats and Duckfat for Belgian-style frites and luscious milkshakes. Along the same block, head to Eventide Oyster Co. for fresh-shucked bivalves and its sister establishment, The Honey Paw , for boldly flavored pan-Asian cooking. Newer chef-driven spots such as locavore-minded Twelve and warmly convivial Thistle & Grouse are turning heads with their inventive, artfully prepared cuisine. And James Beard Award-nominated chefs are well represented in town; consider Krista Cole of Sur Lie (she also runs Gather , just up the road in Yarmouth), Courtney Loreg of Woodford Food & Beverage , Isaul Perez of Isa Bistro and Jake Stevens of Leeward , to name just a few. Allagash , Bissell Brothers and Austin Street are among the more than two dozen craft breweries making waves in and around Portland, while purveyors of everything from artisan baked goods (the Holy Donut , Forage , Norimoto ) to locally roasted coffee ( Tandem , Bard , Speckled Ax ) appear in seemingly every direction. Prepare to be blown away.

The islands of Casco Bay

If you have an extra day, consider taking a cruise among the nearly 150 islands of Casco Bay; six can be reached by scheduled ferry service with Casco Bay Lines from downtown Portland. You can rent a bike near the terminals of most of the islands if you're up for a two-wheel adventure, or just go for a cruise. The sunrise and sunset runs are especially scenic, while the mailboat run lets passengers soak up the scenery as workers deliver mail to several of the islands. For a longer visit, consider booking one of the many vacation rentals on the islands, or staying at one of the few full-service hotels, such as the Inn at Diamond Cove on Great Diamond Island.

As you continue up the coast from Portland, you'll encounter the one span of this itinerary that's best undertaken via a dull but efficient freeway. Hop onto Interstate Highway 295 for the nearly 20-mile drive to Freeport, an attractive and historic town that's both a suburb and a retail hub, thanks to the presence in the heart of downtown of the renowned gear and sportswear store L.L. Bean . Established here in 1912, this massive flagship store is open 24/7 and is a must for stocking up on everything from boating and skiing equipment to tasteful housewares and practical yet attractive fleeces, sweaters, boots and more. A crop of other name-brand retailers have outlet shops within walking distance of L.L. Bean.

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Set in an imaginatively transformed 1850s mill building in downtown Biddeford, the artful Lincoln Hotel (rates start at $334 per night) contains 33 spacious, industrial-chic rooms with brick walls, gas fireplaces, soaring ceilings and huge windows. It's an excellent choice for taking advantage of Biddeford's increasingly acclaimed culinary scene. Close to Portland Head Light and convenient to downtown Portland but with a peaceful setting on Cape Elizabeth's idyllic Crescent Beach, the pet-welcoming Inn by the Sea (rates start at $495 per night) has 62 individually designed rooms with casually opulent decor; suites have full kitchens.

The seven-story Press Hotel (rates start at $432 or 67,000 Marriott Bonvoy points per night) occupies a 1920s Old Port building that once housed the city's newspaper and has been given new life as a hip 110-room hotel with old-fashioned writing desks, local art, a rooftop deck, lots of comfy common spaces and a scene-y (for Portland) farm-to-table restaurant. Located in Portland's historic West End, The Francis (rates start at $395 per night) is set in an imposing redbrick mansion that had fallen into a state of disrepair before its new owners completed an ambitious two-year restoration. This dashing 15-room boutique inn has light-filled, uncluttered rooms with a modern vibe, and guests can book spa treatments in the hotel's sister property, The Longfellow, just across the street.

On Great Diamond Island, just a 25-minute ferry ride from Old Port, the distinctive Inn at Diamond Cove (rates start at $249 per night) has been created out of late-19th-century army barracks and has spacious, stylish suites, some with kitchens, that feature porches or balconies, and a large pool and acclaimed waterfront restaurant.

Brunswick to Camden 

boston to portland maine road trip

From Freeport, U.S. Route 1 continues to the dapper college town of Brunswick (home to Bowdoin College and arguably the state's most famous artisan ice cream purveyor, The Gelato Fiasco ), before becoming a less-trafficked and generally quite scenic two-lane road as it meanders in an east-by-northeast direction through Maine's storied Mid-Coast region. It's about a 60-mile drive from Brunswick to Camden, much of it through lively village centers lined with colonial and Victorian houses and storefronts.

You won't see the actual coastline along this section of road, but numerous state roads run south from U.S. Route 1 down to the picturesque tips of several craggy peninsulas, leading to fabled sites of natural beauty like the Giant's Stairs on Bailey Island, Popham Beach in Phippsburg and Pemaquid Point in Bristol. Detouring down these winding, slow-going roads can easily take an hour or more round-trip, without stops, so unless you have lots of time on your hands, don't attempt to explore every one. But do try to set aside time for at least one of these rewarding side excursions, as it's when you get off the beaten path and experience this region's windswept beaches and dramatic rock formations that you gain a true sense of coastal Maine's sheer beauty.

Bath and Boothbay Harbor

Continue on U.S. Route 1 from Brunswick to the bustling small city of Bath, whose location along a deep stretch of the Kennebec River has made it a hub of shipbuilding since the mid-18th century. Thousands of vessels, including striking wooden clipper ships, were built in the shipyards that formerly lined the riverfront, and the grand Federal and Victorian homes that you see throughout town are a testament to the wealth derived from this important industry. On the south side of downtown, Bath Iron Works opened in 1884 and has built countless warships for the U.S. Navy. It continues to function in this capacity as a division of General Dynamics Corp.

You can learn about the town's, and the state's, rich shipbuilding legacy at the outstanding Maine Maritime Museum , which opened in 1971 on the site of the historic Percy & Small Shipyard. This rambling 20-acre campus contains dozens of carefully preserved buildings along with a terrific museum with an impressive permanent collection of nautical art, ship models and memorabilia, as well as excellent rotating exhibits. On your visit, set aside time to take one of the nature and lighthouse cruises that the museum conducts along the Kennebec River.

From Bath, shortly after passing through historic Wiscasset (home to the famous lobster shack Red's Eats ), turn right onto state Route 27 and continue south to Boothbay Harbor, an idyllic yachting enclave that's home to several stunning lodgings as well as a handful of colorful boutiques and convivial seafood restaurants. Boothbay Harbor's greatest draw is the expansive Coastal Maine Botanical Gardens . Peaceful trails lace the more than 300 acres of formal plantings, a delightful children's garden, shady riverside woodlands and art installations, including five whimsical, larger-than-life troll sculptures that Danish artist Thomas Dambo fashioned out of recycled wood.

Back on U.S. Route 1, you'll continue through several attractive small towns, including Damariscotta, known for its oyster farms and beautiful Victorian buildings. River House and King Eider's Pub are a couple of excellent spots in town to enjoy the local seafood.

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You'll find some of Mid-Coast Maine's most bewitching scenery along the shore of West Penobscot Bay, starting with Rockland. Once a rough-and-tumble hub of commercial fishing and lime quarrying, and later a supply center serving the needs of the region's swankier resort communities, this town of about 7,100 has enjoyed a recent renaissance thanks in part to the opening of the renowned Farnsworth Art Museum , known for its remarkable collection of works by Andrew Wyeth (as well as his father, N.C., and son Jamie). The museum also features the works of many other notables of American painting and sculpture, including Louise Nevelson and Marsden Hartley. The Farnsworth is the centerpiece of Main Street, whose striking redbrick Italianate buildings house one-of-a-kind shops and eateries.

A block away, the strikingly sleek Center for Maine Contemporary Art , which acclaimed architect Toshiko Mori designed in 2016, is another cornerstone of the town's remarkable creative scene. Rockland supports an increasingly robust dining scene, with Primo and the ethereal Mediterranean cuisine of James Beard Award-winning chef Melissa Kelly leading the way.

Before heading north toward Rockport, make the easy 15-minute detour southeast to Owls Head Lighthouse , a stout white lighthouse that's notable for its dramatic setting atop an 80-foot bluff that guards the entrance to Rockland's busy harbor. Climb to the top of this 1852 structure for a rewarding view of Penobscot Bay and the nearby island of Vinalhaven, to which ferry service is available from downtown Rockland; there's a small, informative museum at the base. Home to more than 150 meticulously maintained antique cars, motorcycles and planes, the Owls Head Transportation Museum makes for a fun stop on your way back to Rockland.

Rockport and Camden

U.S. Route 1 continues north along Penobscot Bay through quaint Rockport, a venerable artists colony set around a glorious little harbor and home to destination-worthy restaurants like 18 Central Oyster Bar and, turning out seasonally sourced Maine-meets-Mediterranean fare, Nina June . Turn right onto U.S. Route 1A and follow this narrow, twisting road through the village and around to Camden City Park, a slice of greenery set on a bluff with commanding views of the antique wooden-masted sailboats and schooners in Camden Harbor. It has access to a wonderful little beach, too.

In Camden, an affluent summer getaway that's famous for its fleet of historic Windjammer ships, several outfitters in town offer sails on the bay. Stroll around downtown, relax in the Olmsted Brothers-designed Harbor Park or make the short but rather steep 1.1-mile round-trip hike up to the top of Mount Battie in Camden Hills State Park . From the historic observation tower at the top, to which you can also drive, the bay views are stupendous. Back in town, alluring restaurants await, such as Long Grain , for some of the tastiest Thai food in the Northeast, and 40 Paper , with its oft-changing menu of flatbreads, pastas and charcuterie focused on locally sourced ingredients.

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A stately 1860s captain's house with additional rooms in adjacent buildings, the Topside Inn (rates start at $369 per night) sits on a hilltop with a gracious lawn and sweeping views of Boothbay Harbor. It's a short stroll from local shops and restaurants and a great base for visiting Coastal Maine Botanical Gardens and the Maine Maritime Museum.

Overlooking the harbor in the heart of downtown Rockland, the stylishly modern 250 Main Hotel (rates start at $358 per night) has 26 spacious, high-ceilinged rooms on five floors, along with a rooftop deck with fantastic views of the water and downtown. The thoughtful staff tends to guests' every need, and amenities include a light complimentary breakfast and afternoon wine and cheese.

One of Mid-Coast Maine's most luxurious hideaways, the Camden Harbour Inn (rates start at $555 per night) is part of Relais & Chateaux and enjoys a spectacular setting on a hill with expansive views of the town harbor. This 20-room property features an inn and the critically acclaimed restaurant Natalie's; it's also a short walk from downtown dining and shopping. A half-mile up U.S. Route 1 from downtown Camden, Whitehall (rates start at $231 per night) occupies a 19th-century sea captain's mansion that's been given a clever, boldly colored 21st-century makeover. The 36 rooms and suites are set among a few buildings and range from plush and expansive to simple and economical (with bathrooms down the hall).

Camden to Bar Harbor

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There are essentially two ways to get from Camden to Bar Harbor, which is just 40 miles east as the crow flies: the long way, following U.S. Route 1 up around Penobscot and directly across to Ellsworth, and the really long way, which entails detouring extensively down through the beautiful Blue Hill Peninsula and onto pastoral Deer Isle before cutting back up to Ellsworth.

The first option takes a little under two hours without stops, while the second option can take as long as four hours depending on how many of the Blue Hill Peninsula's nooks and crannies you decide to explore. This side excursion is well worth the time if you're not in a rush. Either way, from Ellsworth, it's an easy drive down state Route 3 onto the eastern shore of Mount Desert Island to get to Bar Harbor.

As you drive northeast along U.S. Route 1, skirting the western shore of Penobscot Bay, you'll pass through the small beach town of Lincolnville, which is where you can pick up the ferry to the attractive summer vacation island of Islesboro, before entering one of the coast's most alluring small towns, Belfast. With a downtown abundant with grand centuries-old homes and shopfronts with ornate brick facades, the governmental seat of Waldo County is a pleasure to explore on foot. You'll find a smattering of generally casual bars and eateries in town, plus some intriguing antiques and housewares shops.

Searsport and Bucksport

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As you continue up U.S. Route 1, more antiquing awaits in the friendly village of Searsport, which is also worth a visit for its superb Penobscot Marine Museum . About 10 miles north, right before the road crosses the Penobscot River, make a left turn and follow the signs to Fort Knox Historic Site and the Penobscot Narrows Bridge and Observatory . Built in 2007, the soaring cable-stayed Penobscot Narrows Bridge is home to the world's tallest bridge observatory; take the elevator to the top of the 420-foot-high West Tower to enjoy the 360-degree views. Then return to earth and stroll the grounds of the adjacent Fort Knox, a formidable granite fortress constructed in the mid-19th century.

After driving across the Penobscot Narrows Bridge, you'll come to the small riverfront town of Bucksport, a former mill town that's reinvented itself as a burgeoning center of tourism. The walking path along the riverfront makes for a pleasant stroll.

Blue Hill Peninsula and Deer Isle

Bordered by Penobscot Bay to the west and Jericho Bay, Blue Hill Bay and Mount Desert Narrows to the south and east, the mostly rural and incredibly peaceful Blue Hill Peninsula is about 25 miles long and contains just a handful of unpretentious yet dignified villages and a cluster of atmospheric country inns and reliable restaurants. As you drive along its curving country roads and alongside its pebbly beaches and graceful bays, it's easy to imagine you're seeing a slice of coastal Maine much as it probably looked a century ago. Home to several conservation areas and nature preserves, the peninsula is popular for hiking, with 934-foot-tall Blue Hill Mountain among the best destinations for a not-too-strenuous 2-mile round-trip scramble, and the views from the top are impressive.

To get here, turn right onto state Route 166 from Bucksport and follow it south along the eastern shore of Penobscot Bay to Castine, a once-bustling colonial seaport that transitioned gradually into a summer colony of understatedly wealthy industrialists in the 19th century. You'll find a handful of endearing shops and eateries in the village center overlooking the harbor.

From here, backtrack up and around Northern Bay and then follow state Route 175 south to a bridge and then a causeway leading to 30-square-mile Deer Isle, with a pair of winsome villages, Deer Isle proper and Stonington, with still more appealing boutiques, galleries and eateries. Home to one of the state's most famous farm-to-table restaurants, Aragosta , Deer Isle attracts more than its share of foodies. Return to the main route by crossing back onto the peninsula and taking state Route 175 or 172 northeast to the peninsula's largest town, Blue Hill, which is still pretty tiny (the population is slightly fewer than 1,000 souls).

Follow U.S. Route 1 and then state Route 3 onto Mount Desert Island, home to the postcard-worthy resort town of Bar Harbor as well as most of Acadia National Park . Bar Harbor was established as a fishing and shipbuilding town in the 1760s, but by the middle of the next century, prestigious American landscape painters, including Thomas Cole and Frederic Church, were drawn here by the captivating harbor, towering granite cliffs and mountains, and sheltered beaches. The town soon attracted wealthy visitors, many of whom, including Rockefellers, Astors and Vanderbilts, erected massive summer homes. The downtown is one of the prettiest, albeit busiest during the summer high season, in the state.

From May through October, cruise ships tie up in the harbor and ferry passengers into town, resulting in sometimes excessive crowds. That being said, the lovely Main Street is lined with appealing shops and eateries, and both the Village Green and waterfront Agamont Park are enchanting spots to relax, perhaps with a slab of fudge or a dish of ice cream from one of the countless sweets shops. Pro tip: Mount Desert Island Ice Cream , which now has locations as far away as Japan, serves the best frozen desserts in town, with unique flavors like coriander-lemon curd and hojicha (roasted green tea). Make sure to visit the two excellent history museums in town, the Abbe Museum , a Smithsonian-affiliated property devoted to interpreting Maine Indigenous culture and natural history, and La Rochelle Mansion , the Gilded Age "summer cottage" of George Bowdoin that opened as a museum in 2020.

Acadia National Park

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Home to the highest peak on the Eastern Seaboard (Cadillac Mountain, elevation 1,530 feet) and remarkably diverse landscapes of rugged and rocky coastal headlands and pristine forests and beaches, Acadia National Park is one of the great natural treasures of New England. About 77 square miles, the park covers around half of Mount Desert Island, mostly on the eastern of the island's two lobes; the rest of Acadia is on Isle au Haut (reachable by ferry from Deer Isle), a number of small and mostly uninhabited islands in the vicinity, and the southern end of the Schoodic Peninsula. Most visitors focus their efforts on the portion of the park adjacent to Bar Harbor, which is indeed an excellent place to start, although this section of Acadia also receives the greatest number of visitors and can feel a bit overwhelming in summer, especially on weekends.

After stopping by the park's Hulls Cove Visitor Center, drive the breathtaking 27-mile Park Loop Road, absorbing the views from the many rocky ledges. Enjoy lunch at the historic Jordan Pond House restaurant. It's famous for its fluffy fresh-baked popovers with butter and strawberry jam.

Although you can drive to the summit of Cadillac Mountain, parking is limited and reservations are required between mid-May and mid-October to drive to the summit. If you love getting outside and you're ready for a break from driving, consider hiking to the top instead. Several trails, ranging in length from around 2 to 7 miles round-trip, lead to the summit. Other appealing treks in the park include neighboring and less crowded Dorr Mountain and climbing the ladders and rungs of the short but quite vertical Beehive Loop, which overlooks one of the park's loveliest stretches of shoreline, Sand Beach. If you have an extra day or want to get away from the crowds, set aside a few hours to explore the park's quieter western side, checking out the trails around Beech Mountain and Echo Lake.

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A luxurious base that's close to both Camden and Belfast yet not far from the Blue Hill Peninsula, the exquisitely restored Homeport Inn and Tavern (rates start at $179 per night) is a short walk from Searsport's town park and fishing pier. This 1860s sea captain's house has a warmly lit British-style pub serving elevated comfort fare, and many rooms have terraces overlooking the verdant gardens.

Famous for having one of the state's most celebrated restaurants, Aragosta at Goose Cove (rates start at $360 per night) offers overnight stays in nine dog-friendly cottages with kitchenettes and three suites, all of them steps from the sea (and some of them with direct water views). It's in the quiet village of Deer Isle, far from crowds, even in the middle of summer. The Blue Hill Inn (rates start at $237 per night) is one of the true gems of the Blue Hill Peninsula. This 1830s mansion decorated in the Federal period style has 11 upscale rooms, and there are two more contemporary suites in an adjacent Cape House cottage. Rates include a lavish multicourse breakfast, and the inn is within walking distance of the harbor and several popular restaurants.

With one of the most desirable locations of any hotel on Mount Desert Island, the refined Bar Harbor Inn & Spa (rates start at $469 per night) sits on a promontory with stupendous views of Frenchman Bay and a wealth of amenities, including an infinity pool, a full-service spa and three waterfront restaurants; many rooms have balconies with water views. The inn accesses the town's famous coastal Shore Path and is an easy stroll from numerous restaurants, shops and the sightseeing cruises that depart from the town pier. The owners run a few other first-rate properties in town, including the Bar Harbor Grand Hotel (rates start at $409 per night), a contemporary reconstruction of a baronial 19th-century inn that was lost in a fire.

The stylishly updated Salt Cottages (rates start at $505 per night) date to the 1940s and are a 10-minute drive from downtown Bar Harbor, across the road from Hulls Cove Beach and right by the Hulls Cove Entrance to Acadia National Park. Popular with families, this welcoming beachy-chic resort offers a host of amenities, from a pool and hot tub to lawn games and a fire pit with s'mores. For a quieter stay away from the bustle of Bar Harbor, book a room at the beautifully renovated Claremont Hotel (rates start at $529 per night), overlooking Somes Sound in Southwest Harbor, on the more tranquil western half of Mount Desert Island. It's a great base for exploring the trails in Acadia National Park's west side, and this 6-acre property features a large pool, three excellent restaurants and a wide range of accommodations options, from classic hotel rooms to houses with multiple bedrooms.

Bar Harbor to Lubec

boston to portland maine road trip

After returning to U.S. Route 1 from Mount Desert Island, it's about a 90-minute journey — the final 15 minutes on state Route 189 bring you to the town of Lubec, which is the easternmost point in the contiguous United States. This is the most sparsely populated stretch of Maine's coast. It's punctuated by a few hardscrabble fishing, farming and timber towns, and the natural scenery along the smaller roads leading out to the coast is beautiful, but there aren't a lot of dedicated attractions in this region. One notable exception to keep an eye out for as you zoom along U.S. Route 1 is the Wild Blueberry Heritage Center in tiny Columbia Falls, which occupies a distinctive pale-blue geodesic dome building meant to resemble a bulbous blueberry. It's one of those goofy roadside stops that's fun for a photo op. Inside the building, a small nonprofit museum has exhibits about the state's most famous crop and a gift shop selling all things blueberry-themed.

For the most part, car traffic dwindles to a trickle, even in summer, once you drive east of Ellsworth. At the end of the road, however, Lubec and neighboring (across Johnson Bay) Eastport are inviting villages free from excessive development. For fans of seaside solitude, it's worth tacking on an extra day or two to complete the drive to the Canadian border.

Even if you're not planning to go all the way to Lubec, consider driving at least as far as the small, laid-back village of Winter Harbor on the Schoodic Peninsula, which dips down into the Gulf of Maine just 5 miles across the water from Bar Harbor. In summer, you can take a passenger ferry between the two towns; otherwise, it's an hour's drive up and around Frenchman Bay. At the southern tip of the peninsula, off state Route 186, you can enter the nearly 4,000-acre Schoodic District of Acadia National Park, with its largely untrampled conifer forests and bike-friendly scenic park loop road and gravel paths. Only a tiny fraction of visitors ever make it to this pristine and highly underrated section of the park that's anchored by the Schoodic Institute , a 1930s mansion that once held offices and living quarters for the U.S. Navy base that occupied the land before it was transferred to the park in 2002. The building now houses a visitor center and a small museum with exhibits on natural history and the peninsula's interesting military history.

A mellow fishing village surrounded on three sides by water, scenic Lubec has just under 300 residents and an unpretentious downtown with a handful of casual lodging and dining options. After spending the night in town, you can rise early and drive to nearby Quoddy Head State Park to watch the sunrise from the nation's easternmost point. Set aside an hour or two to walk around the 49-foot-tall candy-striped West Quoddy Head Lighthouse and explore the park's peaceful, windswept nature trails.

Campobello Island

boston to portland maine road trip

Another enjoyable activity in this part of the world is driving over the only bridge onto Canada's Campobello Island (from the Canadian mainland, you can get to this wooded island of about 950 residents by ferry only). The main event here is visiting Roosevelt Campobello International Park , the 2,800-acre summer hideaway of Franklin and Eleanor Roosevelt. You can tour the 1897 shingle-style house and learn more about the couple in the excellent visitor center. Don't forget to bring your passport!

Tantalizingly within view of both downtown Lubec and Roosevelt Campobello International Park, this historic village on the southeastern tip of Moose Island is only reachable (by car, at least) by driving about 45 minutes around Cobscook Bay. (In summer, there is a passengers-only water taxi that runs between Lubec and Eastport.) Despite feeling even more remote than Lubec, Eastport's downtown actually has more in the way of infrastructure, with a waterfront historic district that comprises a few blocks of handsome Victorian buildings containing a smattering of galleries and cafes. Horn Run Brewing occupies one of the prettiest buildings in town and serves well-crafted brews and tasty pub fare, with a tree-shaded patio looking across the Passamaquoddy Bay toward Canada's Deer and Campobello islands. Stop by the Tides Institute & Museum of Art , which is set inside a vintage bank building and contains rotating exhibits.

Optional side trip to St. Andrews, New Brunswick

You could easily continue your coastal explorations by crossing onto the Canadian mainland and driving farther into the Maritime Provinces. From the border crossing between Calais, Maine (which is a half-hour drive up the St. Croix River from Eastport), and St. Stephen, New Brunswick, it's just an hour or so to the province's largest, and Canada's oldest, incorporated city, St. John. From there, plenty of travelers continue on to Prince Edward Island and Nova Scotia.

But even if your goal is to return to your starting point in southwestern Maine, you might consider making a quick side excursion to St. Andrews, which is just a half-hour southeast of the Calais-St. Stephen border crossing. This colorful maritime village perched at the tip of a peninsula that juts into Passamaquoddy Bay is known for its quaint downtown art galleries, seafood eateries and colonial houses. It's also home to several upscale inns and hotels, including the gracious, Tudor Revival-style Algonquin Resort.

boston to portland maine road trip

En route from Bar Harbor to the Schoodic District of Acadia National Park, the enchanting Crocker House Country Inn (rates start at $210 per night) sits near the tip of a secluded peninsula, Hancock Point, an easy stroll from the Frenchman Bay waterfront. The 11 rooms in this 1884 inn received a dapper renovation in 2022, and the inn's restaurant serves exceptionally tasty contemporary American and Asian specialties.

At the Inn on the Wharf (rates start at $130 per night) in tiny Lubec, you can stay in the easternmost town in the United States while enjoying a view from your room of the sun setting to the west over the water. The inn operates out of a former sardine factory but also has rooms in several contemporary cottages on a hill overlooking the bay. A casual restaurant serves simple, fresh seafood, and whale-watching excursions are offered on the inn's 26-passenger boat. In Eastport's downtown historic district, the Kilby House Inn (rates start at $150 per night) is set in a pretty Queen Anne house with four period-furnished rooms with antique beds and country quilts; a full breakfast is served in the dining room each morning.

If you decide to hop across the border for a night or two, consider staying at the elegantly restored Algonquin Resort St. Andrews by-the-Sea (rates start at $218 or 40,000 Marriott Bonvoy points per night), which is in the quaint seaside village of St. Andrews, New Brunswick. A member of Marriott's Autograph Collection, this red-roofed late-Victorian hotel has 233 stylishly appointed rooms, five restaurants and bars, a luxurious spa, and an award-winning 18-hole golf course.

Pure Wander

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.

sunset at the cliff house maine

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.

boston to portland maine road trip

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.

cliff house ogunquit main lobby and lounge with cliff views

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.

balcony overlooking the ocean at the cliff house in maine

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!

window view cliff house ogunquit

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.

eileen in a mirror at the cliff house spa in maine

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.

lounge area cliff house spa maine

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

boston to portland maine road trip

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.

dessert ice cream sandwich cliff house maine

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.

ll bean flagship store freeport

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.

moose taxidermy ll bean store freeport maine

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?

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Join the discussion 19 Comments

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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.

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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.

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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!

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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.

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

boston to portland maine road trip

Good catch!

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

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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.

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Nice trip. Great pics that you are posting.

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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

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

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Road Trip: Boston to Portland, ME

Image 1

A road trip from Boston to Portland, ME is an exciting adventure that takes you through the stunning beauty of New England's coastal towns, charming lighthouses, and rolling hills. This relatively short journey makes for an ideal weekend getaway, offering a chance to escape the hustle and bustle of city life. Along the way, you'll discover several hidden gems and picturesque spots perfect for taking photos. From indulging in fresh seafood to exploring the nooks and crannies of New England, there are many exciting activities to enjoy on this road trip.

History of Portland, ME

Portland, Maine, has a rich and storied history dating back to the 17th century. Established as a fishing and trading village, the city has transformed into a bustling hub of culture, art, and commerce over the years. With its picturesque cobblestone streets, historic architecture, and stunning waterfront views, Portland offers an alluring blend of old-world charm and modern sophistication.

Portland ME view

What Kind of Car You Should Rent to Get to Portland, ME

When planning your trip from Boston to Portland, choosing the right car for your journey is essential. Kyte offers a wide range of options, from economy cars for budget-conscious travelers to spacious sedans and SUVs for those seeking comfort and style. For winter trips, consider renting an AWD vehicle to easily navigate snowy and icy roads. Additionally, if you plan on exploring the great outdoors or participating in water sports, an SUV with ample storage space for your gear might be the best choice.

How to Get to Portland, ME from Boston

The journey from Boston to Portland, ME, is a scenic drive that takes approximately two hours. Begin by getting on I-95 N in Peabody from US-1 N, a 15.8-mile stretch that takes about 26 minutes. Continue on I-95 N for 90.1 miles, passing through New Hampshire and entering Maine. Keep left at the fork to stay on I-95 N, and then keep right at the next fork to continue on I-295 N, following signs for South Portland/Downtown Portland. Finally, take exit 7 from I-295 N onto Franklin St in Portland.

The Route from the Boston Logan International Airport

Kyte services Boston Logan International Airport (BOS) from a handover spot near BOS, not on airport property. The handover location is at South Station, located at 700 Atlantic Avenue. A Kyte surfer will be waiting for you at the front entrance at the corner of Atlantic and Summer St.

To reach South Station, take a 15-20 minute rideshare or use public transit, which takes approximately 20-25 minutes. Follow signs for the Silver Line from the airport's arrivals area and take the train towards South Station. Trains stop at the Airport T Station every 10 minutes.

Once you have your Kyte, get on I-93 N and travel 0.6 miles before taking exit 19 from I-93 N. Then, get on I-95 N in Peabody, and follow the remaining directions as mentioned above.

Alternative Route

For an alternate route from Boston to Portland, follow these instructions:

Merge onto I-93 N via the ramp on the left toward Concord, New Hampshire, and continue for 22.5 miles. Take exit 40A to merge onto I-495 N and drive for 23.4 miles. Continue onto Exit 60 (signs for MA-286/Beaches/Salisbury) and travel 0.6 miles before merging onto I-95 N. This will take you through a toll road entering New Hampshire and, subsequently, Maine. Keep left at the fork to stay on I-95 N, then keep right at the next fork to continue on I-295 N, following signs for South Portland/Downtown Portland.

Safety Tips for Driving From Boston to Portland, ME

When embarking on your journey from Boston to Portland, remember to stay alert and be aware of changing road conditions, particularly during winter months. Check the weather forecast and road conditions before you leave. Drive at a safe speed and maintain a safe distance from other vehicles, especially when roads are slippery or visibility is low.

Attractions in Portland, ME

Portland is a vibrant city filled with exciting activities and attractions for visitors of all ages. From water sports to hiking, shopping, and dining, there's something for everyone in this picturesque coastal city.

Boats docked

Water Sports

Nestled along the picturesque shores of New England, Portland is a coastal haven for water enthusiasts seeking both relaxation and adventure. The city's stunning coastline, characterized by rugged cliffs, pristine beaches, and charming lighthouses, invites visitors to partake in a range of water-based activities. Renting a kayak or stand-up paddleboard is a popular choice for those who wish to leisurely explore the serene waters of Casco Bay, where they can glide through calm inlets, admire the captivating scenery, and observe the area's diverse marine life.

For those seeking a more exhilarating experience, Portland offers ample opportunity to set sail on a thrilling nautical adventure. Numerous sailing schools and charter services are available, catering to sailors of all skill levels, from novices to seasoned experts. Alternatively, visitors can embark on a whale-watching tour, providing an unforgettable encounter with majestic creatures like humpback and minke whales. These guided tours not only offer an adrenaline-pumping experience but also allow guests to learn about the region's rich maritime history and the importance of conserving its marine ecosystems.

Hiking and Biking

Portland is not only a haven for water enthusiasts but also a paradise for those who love hiking and biking. The city features an extensive network of trails and parks that cater to outdoor adventurers of all skill levels. One of the most popular routes is the Eastern Promenade Trail, a scenic pathway that meanders along the waterfront, providing breathtaking views of the city's skyline and the sparkling waters of Casco Bay. The trail is ideal for a leisurely walk, jog, or bike ride, and it also connects to several other trails in the area, offering endless opportunities for exploration.

For those seeking a more challenging adventure, Portland is just a short drive from several state parks that boast a variety of trails through diverse landscapes. Bradbury Mountain State Park is a favorite among hikers and mountain bikers alike, offering a mix of easy and more difficult trails that lead to the summit, where visitors can enjoy panoramic vistas of the surrounding countryside. Meanwhile, Wolfe's Neck Woods State Park provides a tranquil escape amidst lush forests and picturesque shorelines. With its well-kept trails that wind through dense forests, salt marshes, and rocky shorelines, this park is a great place to really get into nature.

Shopping and Dining

Downtown Portland offers a unique shopping experience, with numerous local boutiques, art galleries, and specialty shops. Stroll along the historic Old Port district, where you'll find charming cobblestone streets lined with an array of shops and restaurants. Portland is also a food lover's paradise, offering diverse culinary options from farm-to-table eateries to fresh seafood and award-winning craft breweries.

Annual Festivals in Portland, ME

Portland is home to several annual festivals that draw visitors from far and wide. One of the most popular events is the Old Port Festival, held every June in the city's historic district. This lively celebration showcases the best of Portland's music, art, and food scenes, featuring live performances, local artists displaying their work, and an array of food trucks and vendors offering delicious cuisine. The festive atmosphere, combined with the charming cobblestone streets of the Old Port, creates a memorable experience for all who attend.

Just north of Portland, in the picturesque coastal town of Rockland, the Maine Lobster Festival takes place every August. This iconic event is a tribute to the region's most famous crustacean and offers a delectable feast of seafood dishes, including the star of the show: Maine lobster. In addition to the mouthwatering culinary offerings, the festival features live entertainment, cooking demonstrations, and activities for the whole family, such as carnival rides, games, and a parade. The Maine Lobster Festival is not only a celebration of the state's thriving lobster industry but also a testament to the strong sense of community that characterizes the region.

As summer turns to fall, Portland's Harvest on the Harbor festival arrives in September, enticing food and wine enthusiasts with a showcase of the best of Maine's culinary scene. This multi-day event highlights the region's talented chefs, local farmers, and artisanal producers, featuring tastings, cooking demonstrations, and food-focused seminars. Attendees have the opportunity to sample a variety of dishes, from innovative farm-to-table creations to classic New England fare, all while enjoying the beautiful waterfront setting.

Portland, Maine, is a captivating destination that promises an unforgettable experience for all who visit. With Kyte's convenient and easy rental car service, you can explore the city and its surroundings at your leisure. Choose the perfect vehicle for your trip and follow the scenic routes from Boston to Portland to experience the best of New England's charm and beauty. From the rich history to the diverse attractions and natural wonders, Portland awaits your arrival.

Boat in the water

Boston to Maine Road Trip: Your Complete Itinerary Guide

Boston to Maine Road Trip

America is hallowed ground when it comes to road trips. Ever since Kerouac published On the Road , the thought of driving around this amazing country has been on everyone’s minds. Whether you want to explore Hawaiian islands or drive from coast to coast, there are endless wonders to be discovered. One option you might be considering is a Boston to Maine road trip.

This is a relatively short trip but also among the most epic. America’s northeastern coast holds spectacular beauty that can be enjoyed at any time of year. Before you set off, though, it’s important to do your research. Make sure you know what to expect, what to pack, how long you need, and where to stop.

This article will help you make your Boston to Maine road trip as epic as possible. Keep reading to increase your understanding of this region. Learn how to prepare for an epic road trip in America’s northeastern states.

Table of Contents

Why Take a Boston to Maine Road Trip?

Boston skyline

The Great American Road Trip is hallowed ground for the traveler. It’s the ultimate expression of freedom and exploration. America is a vast patch of land that requires time to fully understand. That’s why many people choose to rent or buy a car and then journey across different parts of the country. Rather than staying in a single destination, you can get to know this land better by taking to the road.

The question is, which route do you take? Route 66 is perhaps the most famous but at almost 2500 miles (almost 4000 km) in length, this isn’t feasible for most people. Instead, it’s better to choose a shorter route that can be accomplished more quickly. A Boston to Maine road trip is closer to 250 miles, making it doable in a single day. If you’re pushed for time, then this is the perfect way to get all the benefits of a road trip, without spending a lot of money or taking loads of time off work.

Different parts of America offer different benefits for tourists. Yellowstone National Park might be the most beautiful area of the country while southern states might contain more fascinating indigenous history. If you’re into the founding of this great nation, though, then it all begins in the northeast. That’s where Europeans first arrived to found the USA as we know it today. A Boston to Maine road trip is the best way to discover the history of America while traveling through stunning scenery.

How Far is a Boston to Maine Road Trip?

Boston at night

Every road trip will be unique, meaning that the distance you travel will vary. It will vary depending on which part of Boston you start from, where specifically in Maine you end up, which route you take, which sights you want to see, and how far you deviate from the original route. This can drastically alter the total journey time of your trip.

If your plan is to leave central Boston and drive directly to a town in central Maine like Guilford, then your road trip will be a little under 250 miles (400 km). However, most road trippers won’t take such a direct route. Road trips aren’t about getting to a place as quickly as possible. They’re about experiencing and enjoying the journey along the way. They’re about unexpected obstacles and spontaneous detours.

Therefore, it’s best to assume your route will be longer than this. Sit down with a map (either physical or online) and plot the route you want to take. This is the easiest way to see how long the distance really is. The chances are that your total driving journey will be more like 300 to 400 miles (480 – 640 km) long. You’ll then want to add a bit on to account for detours you make along the way.

How Long Does this Road Trip Take?

Boston roads

Like the distance, the time it takes you to complete this journey depends on a number of factors. If you wanted to, you could easily complete the journey in under half a day. After all, the journey time between Boston and Guilford, Maine, is under four hours. You could easily do it in one sitting, without taking any breaks. But what kind of a road trip would that be?

Most people who make this journey want to take their time. They want to stop at beauty spots and historical monuments . They want to get out of the car every now and then to explore this fantastic bit of land. Perhaps you want to stop to eat. Also, you’ll be unlikely to take the quickest route between the start and the end of your Boston to Maine road trip.

Once you’ve added in detours and stoppages, this road trip is likely to take longer than a day. We recommend staying overnight at least once along the way, turning this into a two-day drive, perhaps over the weekend. However, it’s impossible to know exactly how long your journey will take. The point of road trips is that they’re spontaneous and you decide when to stop and when to drive as you go, based on a gut feeling. You’ll only know how long this trip will take once it’s done.

Key Stops to Make

Boston public garden

In order to plan your trip, you need to decide exactly where to stop along the way. These are the key sights that make the trip worth taking. Fortunately, there is plenty to experience along the route from Boston to Maine. The important thing is to decide whether you want to visit natural beauty spots, historical monuments, big cities, or a mixture of all three.

Once you leave Boston, the main urban areas of interest include Newbury Port, Salisbury, Hampton, Portsmouth, York, Portland, Brunswick, and Waterville. There are even more towns further north, depending on how far into Maine you travel. As the names of the towns imply, these were founded by the English as soon as they arrived in the New World. That makes them excellent places to learn about the founding of America.

In terms of natural beauty, you’ll want to stay near the coast for glimpses across the great Atlantic Ocean. The biggest and most beautiful national reserves include Wells National Estuarine Research Reserve and Rachel Carson National Wildlife Refuge. Both of these places are must-visits if you love nature. In terms of monuments, lookout for historical homes, lighthouses, and observatories along the way.

Road Trip Packing Guide

couple on road trip

The Boston to Maine road trip involves traveling through some of America’s coldest destinations so be prepared for this. If you’re from the south, then you probably don’t realize just how cold it can get up there. In Boston – the southernmost point on this road trip – winter temperatures can drop as low as 40°F (-5°C). In this case, you’ll obviously need warm clothes to keep you warm throughout the trip.

Furthermore, the cold brings snow, which you need to be prepared for. Ensure your car is fitted with snow tires and always carry a shovel to dig yourself out of trouble. You should also make sure that your car is always fully stocked with plenty of food and water so you know you’ll be okay if you get stuck.

Of course, you could always make the trip during the summer. In this case, it’ll be much less dangerous and you won’t need to pack so much survival gear. The good thing about this trip – compared to, say, an Arizona desert road trip – is that you’ll never be too far from a town. That means you can pack light and always buy more gear if you need it.

Things to Do When You Get to Maine

Boston cityscape

Your Boston to Maine road trip doesn’t need to end once you reach your final destination. If you’re going to Maine anyway, make sure you have a list of things to do once you get there. This is the perfect chance to round off your trip and end it on a high. With that in mind, research the best things to do in Maine. You can pick your favorite to be your final destination.

What are your favorite things to do? Love American food ? Eat in Maine’s best restaurants. Prefer culture? Visit all the museums. This is your unique itinerary so it’s up to you to do the research and plan the best adventure. However, to get your creative juices flowing here are some of the best things to do in Maine:

  • Explore Acadia National Park
  • Take a trip out to Monhegan Island
  • Marvel at the Victoria Mansion in Portland
  • Wander through the Portland Museum of Art
  • Learn history at the Maine Maritime Museum
  • Have a look around the Nubble Lighthouse
  • Relax on Old Orchard Beach

Maine is full of incredible beauty and fascinating history. A road trip gives you the freedom to explore it at your own pace, prioritizing the things that excite you the most. Make sure you choose something to end your Boston to Maine road trip and use it as motivation to keep on chewing up the miles.

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For more than 11 years, Joe has worked as a freelance travel writer. His writing and explorations have brought him to various locations, including the colonial towns of Mexico, the bustling chowks of Mumbai, and the majestic Southern Alps of New Zealand. When he's not crafting his next epic blog post on the top Greek islands or French ski resorts, he can often be found engaging in his top two hobbies of surfing and hiking.

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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.

Quick Overview of the New England Road Trip Itinerary

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

Getting breakfast at Becky's in Portland, Maine

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

Pafoua sitting looking at Portland Head Light

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

donuts in a case from The Holy Donut

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

Enjoying a lobster roll at the Maine Lobster Company

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.

Another stop on the road trip is Peak's Island

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.

battery steele on Peak's Island

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!

A stop on the road trip is Acadia National Park

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!

Enjoying our meal at Galyn's om the patio on Bar Harbor.

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

IMG 1360

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.

Pafoua hiking beehive trail in Acadia National Park

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.

IMG 1558

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

Eating some popovers at Jordan Pond House in Acadia National Park.

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.

IMG 1717

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!

Bass Harbor Light Station

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

Boats in port

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!

State House in 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.

4 pairs of feet surrounding the Freedom Trail marker on the ground

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.

Old South Meeting House

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.

USS Constitution

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

city of Boston from the boat

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

Front of Mike's Pastry

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

IMG 2244

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

IMG 2275

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!

Paf and friends at Fenway Park

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.

IMG 2285

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!

cemetery on ghost tour

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.

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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)

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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.

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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.

12 Photos From Boston To Portland, Maine (Captured On Road Trips)

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This Underrated Arizona National Park Is Set To Be One Of The Most Popular For 2024

10 arizona road trips that are best taken in winter, underrated, but scenic: this small town in tennessee is a great alternative to nashville.

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.

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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

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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!

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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:

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Plan your summer vacation to Maine

Laura Motta

Jul 8, 2024 • 5 min read

Kids paddle out to an island in a kayak, Maine

Maine has plenty of summer adventures on deck – which one will you choose? © Mike Brinson / Getty Images

Maine is my summer place. I grew up going there with my family, to the region southwest of Portland , where my grandparents owned a three-season lakeside cottage. More recently, I’ve ventured beyond the lakes, especially to Maine’s storied Atlantic coast. My rambles have taken me to quiet coves and packed seafood shacks, to art galleries and antique malls. Here’s how I would plan the perfect summer getaway. 

Pick your home base 

Vibes: This breezy, classic Maine beach town draws crowds of families and older couples all summer long.  

Do: Walk the Marginal Way , a thumbnail of a coastal trail that offers cliff-top views of the Atlantic, jaw-dropping seaside homes and the sprawling beach below.

Eat: Cornerstone , which serves excellent pizzas and craft beer in unpretentious downtown digs, attracts as many locals as travelers. 

Stay: Anchorage by the Sea is an Ogunquit mainstay thanks to its prime seaside location and its emphasis on Maine-style comforts like fire pits, cozy Adirondack chairs on the lawn and a great on-site seafood restaurant. 

View of people walking on a rocky beach, with grass and flowers in the foreground

Vibes: Maine’s largest city manages to feel urbane and lively without ever seeming like it’s overdressed or in a rush. The cobblestone streets of its downtown area are lined with award-winning restaurants and fun shops.  

Do: Get out on the water. Sailing and boat trips of all kinds, from fishing excursions to leisurely sunset cruises, leave daily from the piers near the old port. 

Eat: Central Provisions serves elegantly prepared new American fare in a moody brick-walled space downtown.   

Stay: The Press Hotel , with is black-and-white, typography-inspired design, pays homage to the newspaper that once called the building home.  

Damariscotta

Vibes: Riverside Damariscotta has all the beauty and none of the crowds of its seaside neighbors. It’s also a great base for roadtripping up and down the coast. 

Do: Hop on board with Damariscotta River Cruises to learn about oyster harvesting in the region. You might even catch sight of the harbor seals that swim up river to find dinner. 

Eat: At Bred in the Bone , a Mediterranean-style menu is made exclusively with locally grown ingredients. 

Stay:  The town is devoid of hotels, so vacation rentals are the way to go in and around Damariscotta. 

Booking accommodations

Searching for a summer stay in Maine? Book early. That’s especially true if you’re looking to stay along the coast. Expect limited availability and sky-high prices at the last minute, though you can still score some better rates if you’re staying inland and daytripping to the coast.  

Female hiker and dog at Jordan Pond and The Bubbles, Acadia National Park, Maine

Scheduling your days

Once you’ve chosen your base, plan to spend one or two days there exploring and the rest of your time daytripping. Each of the cities mentioned above unlocks a host of possible excursions, and they’re also easily reachable from each other by car. 

For Ogunquit, head to York with its famous lighthouse at Cape Neddick or go north to Kennebunkport , arguably the most famous Maine beach town.

For Portland, take a culinary deep dive or visit to one of the city’s museums. ( The Children’s Museum and Theater of Maine gets high marks from my four-year-old niece.) Portland also makes a great short trip by itself. If you’re staying in Portland, it’s an easy drive to the rollicking Old Orchard Beach, with its old-fashioned pier and throwback roller coaster . Seaside walks on Cape Elizabeth are also an easy drive from town – just expect to spend some time hunting for streetside parking once you arrive. And the shopping outlets in Freeport were designed for rainy days. 

If you’re staying in or around Damariscotta, a drive to the towns of Rockland and Camden are a must, as is a trip to Boothbay Harbor, which still feels like a small fishing village. 

Because it’s Maine, I’d be remiss if I didn’t mention Acadia National Park , which is a 2.5-hour drive north of Damariscotta, the northernmost base city mentioned above. You can see the park’s highlights in one day by sticking to the main Park Loop Road, but you won’t see everything unless you allocate more time. If you’re choosing this excursion, get an early start to avoid crowds and summer heat. 

A close-up photo of oysters on ice

Plan your meals

Portland’s food scene is a delight, whether you’re on the hunt for burgers, pho, or izakaya. Take the time to plan out your meals here and make reservations, as popular and well-reviewed restaurants may not be able to accommodate walk-ins.

Outside of Portland, lobster rolls, fresh oysters and fried seafood like shrimp and scallops dominate the culinary landscape. Expect waits in July and August at places like Barnacle Billy’s, a classic New England seafood joint with a back patio that overlooks Ogunquit’s Perkins Cove. Stay long enough to see the opening of the cove’s 80-year-old manual footbridge, maybe while sipping the restaurant’s signature rum punch. You’ll find similar salty dog vibes up and down the coast at places like Cape Neddick Lobster Pound (York), Lobster Shack (Ogunquit) and Schooner Landing (Damariscotta). 

If you’re ready to shuck your own oysters or grill codfish steaks on the back patio of your vacation rental, Fisherman’s Catch (Damariscotta) is a charming shop that has fresh seafood but also nicely curated accompaniments like marinades and wines. In Portland, Harbor Fish Market in the old port is the place for oysters and heaps of local charm.  

Getting there and getting around

For travelers who are coming from outside the region, most Maine trips start at Boston’s Logan Airport or at Portland International Jetport. Flights into Boston are more frequent and thus generally less expensive, but you can find lower fares into Portland by booking six to eight weeks ahead. 

You will need a car to do any meaningful exploring outside of Portland. However, the town itself is walkable and it’s feasible to visit for a weekend relying only on your feet and rideshare apps. 

Keep planning your trip to Maine:

Plan a Maine tour with these beautiful road trips Revel in the beauty of the Pine Tree State at Maine's best state parks Enjoy the best of Maine's coast at these amazing beaches

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Bus from Boston, MA to Portland, ME

More travel options, enjoy free onboard entertainment, reserve a seat, need to make a change, on this page, bus stations and stops in boston, ma, boston (south station).

View this address on Google Maps

To view more info about this station, visit our page Boston (South Station)

To view more info about this station, visit our page Brookline

Cambridge (MA)

To view more info about this station, visit our page Cambridge (MA)

Bus stations and stops in Portland, ME

Portland park & ride.

To view more info about this station, visit our page Portland Park & Ride

Portland (East Bayside)

To view more info about this station, visit our page Portland (East Bayside)

Discover all the places you can go

Choose from almost 2,300 destinations with Greyhound, FlixBus and our connecting partners!

Frequently asked questions

The bus trip from Boston to Portland is about 111 miles long. The quickest trip with Greyhound takes 2 hours 15 minutes and you can expect a minimum of 3 stops.

Yes, night trip options are available from Boston to Portland. Check out the route's schedule and choose the best option to suit your plans!

The Boston to Portland bus starts from $23.49. Booking in advance, whether on the app or website, is the best way to get the most affordable bus travel. If you book online, you can choose to pay with a debit card or credit card on the Greyhound app or website. If you prefer, you can also pay in person with cash.

You can track the status of your Boston to Portland bus using Greyhound's bus tracker . With this tool, you can see the real-time location of your bus and get updates on its departure and arrival times.

When traveling on the bus from Boston to Portland with Greyhound, you can bring one carry-on bag with you (maximum 25 lbs, 16x12x7 inches). You can store one bag under the bus for free, and if you have a Flexible fare, the second bag stored under the bus is also free. You can also carry additional or bulky baggage for a supplementary charge. You can reserve extra baggage while booking your ticket on our website or app. Alternatively, you can add bulky items later through the 'Manage My Booking' section. If your departure is from a location with Greyhound personnel, you can book and pay for your extra luggage there. For more information, please refer to our baggage policy page here .

The last Greyhound bus to Portland from Boston leaves at 6:35 pm.

Traveling by bus from Boston to Portland with Greyhound is a convenient and environmentally responsible choice, as bus travel reduces traffic and emissions compared to traveling by car.

Onboard services available on Greyhound buses from Boston to Portland include free Wi-Fi for all passengers, personal power outlets near every seat, reclining leather seats with footrests, extra legroom, overhead storage, and an on-board restroom.

Yes, on this website you can book both Greyhound and FlixBus tickets from Boston to Portland. You can check both the Greyhound and FlixBus ride schedules once you select your departure city, destination city, and desired trip date.

Greyhound runs up to 1 ride per day from Boston to Portland. You can search for your preferred departure date and check the schedule using the search bar above.

Greyhound buses are equipped with wheelchair lifts to assist passengers using wheelchairs or mobility scooters. Each bus has space for two passengers with these devices. It's recommended to book your bus from Boston to Portland in advance to ensure a spot. If you'd like to transfer to a regular seat, our drivers will stow your device for you. Service animals are also welcome on board our buses. For further details on accessibility and service animal policies, please check this link .

You can easily find the bus stops in Boston and in Portland on this page: check the address and their location on the map!

The first Greyhound bus to Portland from Boston leaves at 6:20 pm.

With Greyhound and FlixBus, you can conveniently reach 8 destinations from Portland, including Boston, MA, New York, NY, Bangor, ME.

Plan your bus trip from Boston to Portland with Greyhound

How to book your bus ticket to portland from boston, discover more popular bus connections.

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boston to portland maine road trip

Planning a New York to Maine Road Trip Itinerary

W hether you are going for the beaches and the lobster rolls, or trying to hit peak fall foliage and everything pumpkin and apples, May through October is the perfect time to plan a New York to Maine road trip.

While it is tempting to rush through Southern New England on your way from New York to Maine, take some time to stop and see the sights along the way. This New York to Maine road trip itinerary was designed for a one-week trip, but can easily be extended to include more time at each destination or you can continue up the Maine Coast to see more of Vacationland.

This road trip is designed to go from New York City to Portland, Maine. However, if you want to include more stops between New York and Boston, you will also want to look at my New York to Boston itinerary for additional ideas.

Or, if you want to see more of Maine, you can continue north for a road trip through the Maine Highlands . This itinerary will take you from New York City to Maine, with stops in:

  • Mystic, Connecticut
  • Newport, Rhode Island
  • Boston, Massachusetts
  • Portland, Maine

New York to Maine Road Trip

If you are taking a New York to Maine road trip, the quickest route will be under six hours through Hartford, Connecticut. This makes the best return trip from Maine, but on your way, I’d recommend taking a slightly longer and a smidge more of a scenic route on your way to Maine.

From New York City, take Interstate 95 approximately 3.5 hours (traffic can vary) to the historic seaport town of Mystic, Connecticut. If you need a pitstop along the way, downtown Stamford and New Haven both offer great dining options, or grab some lobster rolls at Ford’s Lobster in Noank, Connecticut.

Stop #1: Mystic, Connecticut

Your first overnight stop should be in the charming seaside town of Mystic. I’m not sure if it is more famous for Mystic Pizza, the 1988 film starring Julia Roberts, or the historic Mystic Seaport, a must-see family attraction. You will probably want to stay here for two nights, as there is plenty to do in town and nearby.

Mystic Seaport is a recreated 19th Century seafaring village, complete with ships, shops, and workplaces staffed with costumed interpreters ready to tell you about their craft and day-to-day life in a 19th Century town. The cooperage, print shop, and general store are all popular stops with kids. Visitors can also step on board the Charles W. Morgan, the last wooden whaling ship in the world, or get out on the water on a Mystic River boat ride.

Downtown you can grab an ice cream and watch the drawbridge go up and down as ships pass by, browse the shops, or get something to eat at one of the many seafood restaurants. In addition to Mystic Pizza, I’m a huge fan of the Engine Room for lunch or dinner, or Kitchen Little for breakfast.

Kids will also love watching the beluga whales at the Mystic Aquarium or exploring the trails at the Denison Pequotsepos Nature Center. If you are visiting in the fall, it is worth waiting in line at B.F. Clyde’s Cider Mill for some hot, fresh apple cider donuts.

If you have time to spend a couple of days, nearby you can enjoy a ride on the Essex Steam Train, a visit to the Pequot Museum on the land of the Mashantucket Pequot Nation, a lighthouse tour from New London, a day at the beach in Misquamicut State Beach in Westerly, Rhode Island, or some wine tasting at Jonathan Edwards Winery near Stonington, CT.

Read more: things to do in Mystic with kids

Where to stay: Hyatt Place Mystic (includes free breakfast) and Mystic Marriott Hotel & Spa (not in downtown Mystic but a good full-service hotel option).

Stop #2: Newport, Rhode Island

From Mystic, it is about one hour drive to your next stop in Newport, Rhode Island. You can potentially just visit for the day and continue on to Providence or Boston, but staying overnight will give you more time on the Classic Coast.

Whether you are visiting in the spring, summer, fall, or winter , there is always something to do in the historic town of Newport, Rhode Island . Once a summer getaway for the wealthy New York industrialists, Newport still attracts the yachting crowd as the “sailing capital” and the classic coast. You can do Newport in a day, as it is only an hour from Mystic, but if you want to enjoy nearby beaches, farms, or take a day trip to Providence, Rhode Island , plan on staying one to two nights.

Two must-do things when you are in Newport are paying a visit to at least one of the famous Newport Mansions and getting out on the water for a sailing tour. The Newport Mansions are former homes of the business titans like the Vanderbilts, which were once used as “summer cottages” but more closely resemble palaces than a beach house. The largest and most famous is The Breakers, but I also enjoy visiting Marble House.

If you don’t want to tour the homes, take a drive down Bellevue Avenue to see them from the front and then walk along the three-mile Cliff Walk to get a glimpse of some of the backyards, along with gorgeous ocean views.

There are many sailing options in Newport, from sunset schooner sails to seal-watching eco-tours (in the winter). Leave time to enjoy shopping and strolling along Thames Street and Broadway in downtown Newport. You can also pop into the International Tennis Hall of Fame or one of two car museums around town. There are plenty of options for a great meal, including Bowen’s Wharf, the Black Pearl, Diego’s, and Midtown Oyster Bar.

In the evening, be sure to take a drive along Ocean Drive and try to catch a sunset from either Brenton Point, the Lawn at Castle Hill Inn, or Newport Island Harbor Resort on Goat Island. On your second day, either hit the beach (my favorites in Newport are Gooseberry Beach and Second Beach) or take a drive over to the neighboring island of Jamestown to visit my favorite spot in Rhode Island, Beavertail State Park. If you prefer an urban outing (or if you are visiting on a Waterfire night), head up to Providence for the day or afternoon/evening.

Where to stay: Newport Marriott has a great location and nautical decor, The Brenton Hotel is a hip hotel in central waterfront location, and The Vanderbilt is an upscale, historic property with a great rooftop bar.

Stop #3: Boston, Massachusetts

When it is time to bid adieu to Rhode Island, drive two hours north to Boston. Now if you have extra time, you will want to spend three days in Boston, especially if you want to take some day trips to Gloucester , Rockport, or Salem, or stop at Plymouth along the way.

Boston is rich in history and charm, and like any large city, it has its fair share of great museums too. If you are interested in history, taking a walk along the Freedom Trail is a must-do. Of course, you may get more out of it if you sign up for a tour with a costumed guide.

To better understand Boston’s pivotal role in the Revolutionary War and founding of the country, pay a visit to the Boston Tea Party Ships & Museum . Kids will especially love tossing the tea into the Boston Harbor or a snack at the tea shop.

Within a short walk of the Boston Tea Party Museum, you can also visit either the Boston Children’s Museum or the New England Aquarium. If you are visiting in the summer, I’d recommend booking a whale-watching cruise in advance for an afternoon on the water and a glimpse of some magnificent creatures. If you don’t have time for a whale watch, you can still enjoy some time on the water with a harbor cruise or a ferry around the Boston Harbor Islands.

Afterward, take a walk along the Rose Kennedy Greenway and either enjoy some of the food trucks congregated there, or walk over to the North End, Boston’s “Little Italy” and pick up some cannoli at Mike’s Pastry. And while it is touristy, the street performers around Fanueil Hall are always entertaining and there are plenty of places to grab a quick bite. For a more upscale food hall, drop into the Boston Public Market or head across town to Eataly Boston.

Sports fans should try to book a tour of the “Green Monster” and Fenway Park or try to catch a Boston Red Sox game in this classic stadium. If you appreciate art, visit the Museum of Fine Arts, or the intriguing Isabella Stewart Gardner Museum nearby (and learn about the famous heist that took place there.)

While you are in town, take a stroll through the Boston Common and Public Gardens, and take a ride on a Swan Boat before you visit the famous “Make Way for Ducklings” sculpture. You can also pop into Cheers on Beacon Hill and see if anyone knows your name. Movie and television fans would also enjoy a tour with On Location Tours of popular Boston filming sites from Good Will Hunting, Ted, The Departed, and others.

Read more: Things to do in Boston with teens

Where to stay : Boston is notoriously pricey, so for a family, you may want to consider one of the following options: Residence Inn Boston Downtown/Seaport Hotel has a convenient location to downtown, North End and harbor; Element Seaport is in newer seaport district with family size rooms; and Hyatt Place Boston/Seaport District has free breakfast and a good location in popular Seaport District.

Stop #4: Kennebunkport, Maine

On your way to Portland, head two hours north of Boston to the charming coastal town of Kennebunkport, Maine. As soon as you pass into Maine, get off the highway and hightail it to Bob’s Clam Hut for some of the best lobster rolls and fried clams in New England. Then meander up the coast, taking your time to stop into a few of the best towns in the Maine Beaches region.

If you need to stretch your legs, stop in York for a walk along the 1.5 mile Cliff Walk or stock up your kitchen pantry at the Stonewall Kitchen company store. Another must-stop destination on your road trip to Maine has to be in Cape Neddick at the Nubble Lighthouse. Located on an island just off the coast, this is one of the most photographed lighthouses in Maine. If you are hungry, you can get some fresh lobster at Fox’s Lobster House right next door or Dunne’s Ice Cream down the street.

Just a little further along you will arrive in Kennebunkport (you might want to drive past the Bush Family compound along the way.) In town, you can enjoy shopping and dining at the many restaurants such as Federal Jack’s, Allison’s, Mabel’s, or the famous Clam Shack.

We also like to head out of town to Cape Porpoise Chowder House, which is popular with locals and tourists alike. Just be warned that parking is hard to find so you may need to walk a bit. You can stay in Kennebunkport or drive another 40 minutes to Portland, Maine. Your final destination on this New York to Maine road trip.

Where to stay: The Boathouse is a waterfront hotel right in Dock Square is perfect for when you want to be in the center of the action. If you prefer a bed and breakfast, try the The Inn at English Meadows .

Stop #5: Portland, Maine

Portland , Maine is one of the best small cities on the East Coast . Plan to spend at least a couple of days exploring Portland and the surrounding area. The park and area around Portland Head Light in Cape Elizabeth is a perfect spot for a picnic and to clamber over the rocks and watch the boats go by. When you are there, be sure to pick up a lobster roll from the Bite into Maine food truck.

Back in Old Port, take an afternoon to explore the boutiques along the harbor and wharves. There are so many amazing restaurants in Portland to try including Luke’s Lobster, Duckfat, Eventide, and Fore Street. There are also many craft breweries in the Portland area and you can board the Brew Bus for a tour if you don’t want to risk driving.

On your second day, you can take a ferry around the Harbor Islands or try a lobster cruise where you learn all about lobster fishing and even get to keep and cook what you catch. Or, spend a day shopping up in Freeport, home of the flagship L.L. Bean store.

Read more: Things to do in Portland in winter

Where to stay: Press Hotel or the AC Hotel Portland

While this New York to Maine road trip itinerary only takes you into Southern Maine, it is easy to extend this to head up to the coast with a stop at either Boothbay Harbor or Rockland before reaching Bar Harbor and Acadia National Park .

This road trip gives you a great introduction to Southern New England and includes some of the region’s highlights. If you are looking for more road trip ideas and want to dig a little deeper into New England, I’d recommend:

  • New England road trips to take in the fall
  • Vermont road trip itinerary
  • Off-the-beaten path Maine road trip

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Plan a New York to Maine road trip with this one-week itinerary on where to stop, things to do, and where to stay.

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Day Trips in Maine: 3 itineraries for eating, drinking and adventuring your way through Vacationland

Summer day trips are a big part of life in New England. We visit our favorite beaches and ice cream spots, and we discover new bookstores and trails.

Journalists from the New England News Collaborative have been on the road, seeking out the best local spots in the region. Find ideas for Maine and other New England states at http://mainepublic.org/daytrips .

Jump to: Portland and Southern Maine | Bar Harbor and Coastal Maine | Rangeley and Western Maine

Maine is known as “Vacationland,” and it really lives up to that name. Whether you want a day trip to the beach, a coastal hike or a mountain lake swim, Maine has it all. As you may have heard, we are known for our seafood, especially our lobster. When it comes to finding the best lobster roll, know that fresher is better, but be prepared to spend some money. We are also known for our spectacular lighthouses and ocean views. You might even see a whale or a moose if you're lucky!

Check out this list of fun things to do, places to see, and food to eat in three key regions of the state — southern Maine and the Greater Portland area; Down East Maine; and the Western Mountains. Know that this is not an all encompassing list but a good place to start your day trip plans.‎

Southern Maine & Greater Portland

Southern Maine and Greater Portland offer a great mix of beach aesthetic and small-city living. Known for its vast array of eateries, Portland in particular is a foodie and beachgoers dream. Plus, there are breweries galore to satisfy all your IPA dreams. As someone who lives here, these are the spots I can thoroughly recommend if you're looking to spend the day eating and exploring in the area.

What to do if you're a...

Beachcomber

If you’re looking to surf, relax with a good book on the sand, or find a spot for your dog to run, these are some of the best beaches in southern Maine.

  • Higgins Beach — This is a great beach for surfing and for lounging. Parking is limited, so make sure to get there early.
  • York Beach — A classic Maine beach with miles of sandy beach to walk, run and play beach games.
  • Ogunquit Beach — A popular beach with a cute downtown within walking distance, Ogunquit also has a natural lazy river that occurs with the tidal change and provides a calm area for kids to play in the water.
  • Old Orchard Beach — This is a busy location, but the beach and activities are well worth it! Ride the Ferris wheel and get some ice cream while you're there.

Lighthouse Geek

  • Portland Head Light — This is a favorite among lighthouse lovers, and is located in Cape Elizabeth, about a 10 minute drive from Portland. The lighthouse is located in Fort Williams Park, with 90 acres of land for walking and outdoor activities. 
  • Spring Point Ledge Lighthouse — A lesser known lighthouse, and my personal favorite, Spring Point Ledge lighthouse is only a 10 minute drive from downtown Portland and offers a great view of the water. Note that it's not easily accessible as it has some large rocks you have to walk across to get to the lighthouse. 
  • Nubble Lighthouse — Located in York, Nubble is a picturesque lighthouse that's classic coastal New England. 

Portland Headlight Lighthouse in Cape Elizabeth, Maine.

  • Evergreen Cemetery — Established in 1854, Evergreen cemetery is the largest in Maine and, as a garden-style cemetery, it offers walking trails and a pond. It's also a great location for bird watching.
  • Portland Fire Engine Co. Tours — Take a guided tour in style! Ride a vintage fire engine while seeing historic landmarks and learning about the city of Portland's rich history.
  • Portland Art Museum — Located in downtown Portland. Note that there is free admission to all 4-8 p.m. Fridays. Through the Portland Art Museum, you can also get tickets to the Winslow Homer Studio tour in Scarborough, and see where the famous Maine painter made much of his work. (Available May 20- Nov. 10, tickets range from $25 to $70.)
  • Longfellow Books — Located in Monument Square, it is easily accessible by foot as you walk through downtown Portland. They have a robust collection of new books and very friendly staff.
  • Cove Street Arts — Check out Cove Street Arts to learn about Maine’s place in American art history and see multidisciplinary art exhibits. Note that they are closed on Sundays and Mondays.

With so many good food options across Maine, you'll be happy we have three meals a day. (Or more, if you dispense with formality!)

  • Scratch Baking Co. — Located in South Portland, Scratch is known for their bagels and baked goods. Make sure to grab some Maine salt bagels, and don’t worry, the line moves fast! Note that Scratch is open Wednesday-Sunday. 
  • Bird and Co. — This taqueria serves brunch on the weekends and has a wide variety of delicious vegan options. 
  • The Highroller Lobster Co. — famous for their lobster rolls, Highroller is conveniently located right in the Old Port and has a bright inside seating area as well as outdoor seating. Make sure to check out their merch as well!
  • Duck Fat — As the name suggests, this restaurant is known for using duck fat to fry their Belgian style fries, giving the food a rich flavor. Don't miss the poutine!
  • Sweet Pea's Ice Cream — Don't forget dessert! Stop by Sweet Pea's after a day at the beach in Ogunquit, Maine.

Sweet Pea’s Ice Cream shop in Ogunquit, Maine on Sunday, June 23, 2024. (Raquel C. Zaldívar/New England News Collaborative)

  • Eventide Oyster Co . — Grab some oysters and fresh seafood at Eventide, and make sure to try their famous brown butter lobster roll.
  • Crispy Gai — Incredible Southeast Asian street food in a casual dining setting. You have to try their famous chicken wings, which come with your choice of sweet or spicy sauces.
  • Allagash Brewing — Take a tour of the brewery, order samples and grab a bite to eat. Allagash White, a Belgian-style wheat beer, put this brewery on the map.
  • Bissell Brothers — Bissell has a large beer selection as well as fun events happening throughout the year, and especially during the summer. 
  • Tomasos Canteen — This is a great casual spot to grab a beer, share some wings with friends and maybe even munch on some fried pickles. Note that they have limited seating.  
  • Oxbow Brewing — Located in Portland’s walkable East End, Oxbow is a great spot to listen to live music and drink an authentic farmhouse ale in their beer garden. Also make sure to grab some Duckfat frites at their takeout window. 

Bar Harbor & Coastal Maine

The Maine coast stretches some 3,500 miles, including bays and inlets — meaning there are a myriad of beaches, islands and coastal towns to explore. Bar Harbor is just one part of the Maine coast, but it's a top destination, with Acadia National Park as a backdrop and a beautiful, quintessential downtown as well. Maine’s Down East region is known for its natural beauty and fresh seafood, especially lobster! I grabbed a coworker and spent the day checking out some of these spots.

Nature Lover

Coastal Maine is a nature lover’s utopia. Near Bar Harbor, the go-to spot is Acadia National Park . Acadia has a perfect mix of coast and mountains and has tons of trails and views for everyone. You will need to purchase a park pass for your vehicle upon entering the park, but note that these passes last for seven days.

If you want a chill outdoors experience…

  • The Ocean Path Trail — This is a flat, 4.5-mile trail along the rocky coastline offering some amazing views of the water and nearby islands. This is a great path for all ages and abilities. You can park along the road parallel to the trail and start walking at any point, or you can park at the start of the trail at Sand Beach. This might be my favorite thing to do in the park!
  • Sand Beach — The name says it all! This beach is tucked between rocky cliffs and provides a great spot to have a beach day, go for a swim or play in the sand with your kids. Be aware that it can be crowded during peak season. Also make sure to take advantage of the free Island Explorer shuttle, which stops at all popular locations in the park, to help you avoid parking in the busy lots. 

If you want something a little more challenging…

  • Cadillac Mountain — The Cadillac summit is famous for being the highest point on the Eastern Seaboard and, depending on the time of year, it contends for the first place to see the sunrise in the U.S. You can either reserve a permit to drive up to the top; get an early start and hike up the Cadillac North Ridge Trail, a 4.2-mile out-and-back trail; or cycle up one of the best-regarded, most challenging bike climbs in the state.
  • The Beehive trail — This is a rung-and-ladder trail, which can be challenging for some hikers and not easily accessible. But if you’re up for the challenge, the 1.4-mile round trip promises great views that overlook Sand Beach and the Gulf of Maine. 
  • Cafe This Way — a cozy breakfast spot with outdoor seating and friendly, quick service. This was a perfect way to start off our day in Bar Harbor. You can even get a breakfast sandwich with French toast as the bread!
  • Looking Glass Restaurant — A great spot for breakfast with a view of the ocean. Make sure to order a Looking Glass-exclusive item.

A french toast breakfast sandwich at Cafe This Way in Bar Harbor, Maine on June 3, 2024.

  • Geddy's — A classic Bar Harbor restaurant located right in downtown. The interior highlights a rustic Maine aesthetic with high-quality food and fresh Maine seafood. Don't forget to order a lobster roll! 
  • Finback Ale House — There are a variety of whale-themed restaurants in Bar Harbor, as visitors can spot humpback, finback, and minke whales off of the coast of Maine. I had some fresh clam chowder and, of course, we had to grab a beer to finish off our day of eating and drinking.
  • Thirsty Whale — If you want more of a tavern feel, visit the Thirsty Whale a few doors down that has a wide variety of seafood, appetizers and specialty cocktails.
  • El El Frijoles – If you are headed down the coast towards Sedgwick, make sure to check out El El Frijoles (a play off of Maine’s famous L.L.Bean). This family-owned summer restaurant serves homemade Mexican food made with local Maine ingredients that you can enjoy indoors in a beautiful screened-in porch area, or share a meal with friends around the outdoor fire pit. 

Lifelong Learner

If you’re a history buff or find yourself in Bar Harbor on a rainy day, there are tons of places to check out.

  • Abbe Museum — Located right in downtown Bar Harbor, the Abbe Museum is the spot to learn about the Wabanaki Nation’s heritage, culture and homeland.
  • La Rochelle Mansion and Museum — If you are interested in turn-of-the-century homes, you need to take a morning or afternoon and walk through the Bar Harbor Historical Society’s well-preserved home from the early 1900s. The mansion offers a look into a classic New England high class home with beautiful grounds and views. 

La Rochelle mansion in Bar Harbor, Maine on June 3, 2024.

If you’re more interested in Bar Harbor’s wildlife and ecology…

  • Mount Desert Oceanarium and Education Center — Here you can meet Maine’s coastal critters including fish and lobster, and learn about coastal habitats.
  • George B. Dorr Museum of Natural History — If you’d rather stay closer to downtown Bar Harbor, check out the College of the Atlantic’s Dorr Museum, where there's a touch tank for all ages to get up close and personal with starfish, crabs and other crustaceans. If you are traveling on the free Island Explorer bus, the shuttle stops right near the Dorr Museum throughout the summer, making visiting easily accessible to all.

If you are an art lover and are traveling down the coast from Bar Harbor, have you ever heard of the giant trolls of Maine?

  • Coastal Maine Botanical Gardens — The trolls are a big attraction at the Botanical Gardens in Boothbay. Their real name is “Guardians of the Seeds,” and they were made by Danish artist and sustainability activist, Thomas Dambo. The botanical gardens have lots of things to see, including gardens in bloom and a butterfly and moth house. They are open May through Oct. 20, and there is an admission fee. This is a great spot for the whole family!
  • Center for Maine Contemporary Art — Make sure to visit the gallery in Rockland. This museum focuses on art made by Mainers or people who are inspired by Maine. It’s a great chance to see and support local Maine art. 

Rangeley & Western Maine

The western mountain and lakes region of Maine is known for winter season activities including skiing, snowboarding and hunting. But the area also is a great summer getaway, with tons of swim spots, hiking trails and places to eat. I would argue this drive is the most scenic in this guide. I made sure to stop by some of these places and see what Western Maine is all about.

Nature lover

  • Winter skiing — The mountain region is known for winter skiing. Check out Saddleback Mountain, Sugarloaf, Sunday River, Mt. Abram and Pleasant Mountain. 
  • Cascade Stream Gorge Trail — For a quick day hike for the whole family, check out this short, 1-mile loop that leads you to see a series of waterfalls. This is a great option for kids.
  • Saddleback Mountain via Ski Lodge trail — If you’re looking for a more challenging day hike, trek the 5.9 miles (about 3.5 hours) up and back.
  • Rangeley Lake State Park — A great spot to camp, swim or enjoy a picnic lunch by the lake on the public access lawn area.
  • Coos Canyon — Check out Coos Canyon on Route 17, located right on the Swift River. There are swimming and cliff jumping spots, plus places where you can pan for gold!

Breakfast...

  • Looney Moose Cafe — Located in Stratton, this might have been my favorite meal of the day! Not only can you eat a hearty breakfast, but they also make homemade doughnuts. Stop by on your way to Sugarloaf to fuel up for skiing or hiking. 
  • The Red Onion — Right on Main Street Rangeley, the Red Onion is a local favorite known for their pizza.
  • Classic Provisions — This is a go-to breakfast and lunch spot in Rangeley. They have a variety of sandwiches and salads, as well as coffee drinks and house-made pastries. Plus you can walk two steps and grab an ice cream next door.

A couple eats ice cream by Haley Pond in Rangeley, Maine on June 19, 2024.

  • Rangeley Inn and Tavern — Not only is this a great lodging spot, but it also has an attached tavern that serves quality food in cozy dining rooms.
  • The Mountain Social Kitchen and Bar — This is a great fine dining option. They have locally made food and are located right on the main street in Bethel. 
  • Furbish Brew House & Eats – Situated on Main Street in Rangeley, you can sip on your brew while enjoying a view of Rangeley Lake.
  • Outdoor Heritage Museum — This is a small but robust museum where the whole family can learn about western Maine’s history of hunting, fishing and wildlife from the 20th century. They even have a 100-year-old cabin!
  • Rangeley History Museum — Stop by to learn about the history of Rangeley and western Maine. This location is right on Main Street. 
  • Maine Mineral and Gem museum — Who knew you could hold a piece of the moon in western Maine? Plus, we even got to touch 7 billion-year-old stardust. This museum has the largest meteorite collection in North America, plus tons of beautiful gems and stones. Their staff can answer all your burning questions about space rocks! Note that admission ends at 4 p.m., while the museum closes at 5 p.m.
  • Did you know that Rangeley is located exactly halfway between the Equator and the North Pole? There’s even a spot on Main Street where you can stand and be exactly in the middle!

Lunar meteorites at the Maine Mineral & Gem Museum in Bethel, Maine on June 19, 2024.

boston to portland maine road trip

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Spirited ‘Funny Girl’ captures excitement of early musical theater

The show that made Barbra Streisand famous is playing at Maine State Music Theatre through July 13.

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Jenna Lea Rosen as Fanny Brice with the cast of “Funny Girl” at Maine State Music Theatre. Photo by MSMT/Jared Morneau Photography

Who are the luckiest people in the world? At least for theater fans, the answer is “people who need people,” a line made famous well over half a century ago by Barbra Streisand in the original production of the musical “Funny Girl.”

THEATER REVIEW

WHAT: “Funny Girl: the Musical” by Maine State Music Theatre

WHERE: Pickard Theater, Bowdoin College Campus, Brunswick

REVIEWED: June 28 (matinee); continues through July 13

TICKETS: Starting at $93

CONTACT: 207-725-8769, msmt.org

On the heels of the show’s recent Broadway revival, the Maine State Music Theatre has opened a spirited production of the classic musical on its home stage at the Pickard Theater on the campus of Bowdoin College in Brunswick.

The show primarily captures the rousing excitement of early musical theater while unavoidably making us think about how it launched the career of Streisand. At a lengthy but enjoyable two-and-one-half hours, plus intermission, it’s a show that still charms with its memorable songs, old-style comedy and bittersweet love story.

The impressive production, directed and choreographed by Kenny Ingram and with the time-honored music of Jule Styne, lyrics by Bob Merrill and book by Isobel Lennart, tells the semi-fictionalized story of Fanny Brice, a real-life figure who rose from humble origins to showbiz stardom as a give-it-everything-you’ve-got performer in the early 20th century.

At first socially awkward and vulnerable, but with a unique talent and an admirable determination to succeed, Fanny gained the attention of famed impresario Florenz Ziegfeld, Jr. and went on to star in many of his glitzy stage shows. At the same time, Fanny’s personal life was a bit of a rollercoaster ride.

Jenna Lea Rosen takes the lead role and scores comedically with her initially wide-eyed approach to Fanny’s personal and professional challenges. Armed with a feisty “New Yawk” accent, the actress easily takes charge of backstage, front stage and offstage scenes. Her vocals are compelling on both comic numbers (“Sadie, Sadie” and “Rat-Tat-Tat-Tat”) and in more intimate moments (“People” and “Don’t Rain On My Parade”). Advertisement

Douglas Raymond Williams plays Fanny’s handsome rogue of a love interest who brings her to a fuller life but fails her in the end. His opera-trained vocals alongside Rosen (“I Want to be Seen With You” and “You are Woman, I am Man”) establish both the heat and uncertainties within their relationship.

Among the many standout secondary actors and choristers, Tyler Johnson-Campion is a tap-dancing whiz. His work with Sue Cella, who plays Fanny’s mom, is a treat on “Who Taught Her Everything.” Cella also has some fun moments squabbling with a competitive friend played by Maine State favorite Charis Leos.

Tommy Betz shines as a Tenor and David Girolmo returns to the Pickard stage as the stern but supportive Mr. Ziegfeld. Jeremiah Valentino Porter gets to toot a hot horn on “Cornet Man.”

The Maine State Music Theatre Orchestra, led by Jason Wetzel, mixes up the period flavors with a newer Broadway expansiveness. The costumes designed by J. Theresa Bush and scenic design by Jeffrey D. Kmiec take the audience back to a distant era when musical theater and its early stars were on the rise.

Steve Feeney is a freelance writer who lives in Portland.

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    This drive covers 110 miles total. For the most scenic drive from Boston to Portland, Maine, go part of the way via the highway-free, coastal route. You'll still take Route 93 to Route 95, but get off at exit 90 to go into the Hampton Beach area of New Hampshire; this should be about an hour's drive to this point.

  5. Road Trip From Boston To Portland, Maine

    The Coastal Route. 110 miles. 1 hours 45 minutes. The Inland Route. 140 miles. 2 hours 10 minutes. The road trip from Boston to Portland covers 110 miles of ground along the quicker route and takes around 1 hour 45 minutes to drive. With a drive this short, you can take off at virtually any hour and make it to Portland in time to do something ...

  6. Boston to Portland, Maine: The Ultimate Guide to Road Trip Routes and

    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 ...

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

    New England fall road trip itinerary. Day 1: Drive from Boston to Maine with a pitstop in Salem, Massachusetts. Things to do in Salem, Massachusetts. Day 2: Portland, Maine. Things to do in Portland Maine. Day 3: New Hampshire | Conway, Lincoln, and White Mountain National Forest. Things to do in New Hampshire.

  8. From Boston to Maine: The Ultimate 3-Day New England Road Trip

    Take a New England road trip and drive from Boston to Portland Maine for a weekend in the summer. Discover places to visit in Maine when you travel from Boston to Maine by Car. ... New England Road Trip Stop #7: Portland, Maine We parked the car in Portland Maine and spent the rest of the day at the end of our Boston to Maine road trip on foot ...

  9. Boston to Portland Maine Road Trip

    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.

  10. Boston to Portland, ME drive

    drive for about 35 minutes. 3:58 pm Portland (Maine) stay for about 1 hour. and leave at 4:58 pm. drive for about 5 minutes. 5:03 pm arrive at Portland, ME. driving ≈ 3 hours. From: City:

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

    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.

  12. Boston to Portland (Maine) drive

    drive for about 37 minutes. 3:33 pm Kennebunkport (Maine) stay for about 1 hour. and leave at 4:33 pm. drive for about 35 minutes. 5:08 pm arrive in Portland (Maine) eat at Duckfat. stay at Portland Regency Hotel & Spa. driving ≈ 3 hours.

  13. Boston To Portland, Maine: 10 Things To Do On This New England Road Trip

    The Kancamagus Highway: a 34-mile (55 km) scenic drive. This stop is a bit of a detour from the main route from Boston to Portland. Be sure to plan appropriately! The Ultimate Pennsylvania Road Trip: Exploring The Kittatinny Ridge And Its Surrounding Beauty.

  14. Guide to the perfect coastal Maine road trip

    Getting to the Maine coast. Boston Logan International Airport (BOS) has by far the greatest number of direct flights in New England, and it's just a 75-minute drive from the Maine border. Another option is to fly into Maine's small, user-friendly Portland International Jetport (PWM), which is a 45-minute drive from Kittery.

  15. 39 Best Stops Between Boston and Portland

    How long is the drive from Boston to Portland? The direct drive from Boston to Portland is 107 mi (172 km), and should have a drive time of 1 hr 49 mins in normal traffic.. If you're going on a road trip from Boston to Portland, we did the research for you and compiled some great stops along the way — with Salem, Ogunquit, Cambridge, Portsmouth, Gloucester, Concord, Kennebunkport, Rockport ...

  16. Boston to Maine Road Trip: Ogunquit, Freeport and Portland

    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.

  17. Boston To Portland: What To See On This Coastal Road Trip

    It's located on Washington Square North. How to get there: Take I-93 North to Exit 28A onto I-95 North. Follow I-95 North to Route 128 North. Take exit 25A and follow Route 114-East into Salem. Follow signs to the Salem Visitor Center. Note: I-95 North and Route 128-North share the same road for the loop around Boston.

  18. Road Trip: Boston to Portland, ME

    The journey from Boston to Portland, ME, is a scenic drive that takes approximately two hours. Begin by getting on I-95 N in Peabody from US-1 N, a 15.8-mile stretch that takes about 26 minutes. Continue on I-95 N for 90.1 miles, passing through New Hampshire and entering Maine. Keep left at the fork to stay on I-95 N, and then keep right at ...

  19. Boston to Maine Road Trip

    Follow this guide to plan the ultimate weekend road trip from Boston to Maine. ... After another 40 minutes on Interstate 95, you'll arrive in Portland, Maine's biggest and most vibrant city. Park in Old Port and spend an hour or two getting lost among the 19th-century warehouses, unique shops, and intriguing museums that line Congress Street. ...

  20. Boston to Maine Road Trip: Your Complete Itinerary Guide

    This can drastically alter the total journey time of your trip. If your plan is to leave central Boston and drive directly to a town in central Maine like Guilford, then your road trip will be a little under 250 miles (400 km). However, most road trippers won't take such a direct route.

  21. 10 day New England Road Trip Itinerary (Portland to Boston Drive)

    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.

  22. 12 Photos From Boston To Portland, Maine (Captured On Road Trips)

    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 ...

  23. New England road trip Boston-Acadia NP: recommended stops?

    Reply to: New England road trip Boston-Acadia NP: recommended stops? Your message. Read our community guidelines. Get notified by e-mail when a reply is posted. Preview. Maine forums . Maine forums . ... Portland, ME . Hilton Garden Inn Auburn Riverwatch. 914 Reviews . View Hotel. Auburn, ME . View all hotels. Maine Destination Experts. CB48 ...

  24. Portland (Maine) to Boston drive

    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.

  25. The New York Times on how to spend 36 hours in Portland

    Travelers in Portland, Maine, a city bursting with culture, restaurants, and outdoor adventures, just received a helping hand from The New York Times. 2 New England destinations made CNN's ...

  26. Plan your summer vacation to Maine

    For travelers who are coming from outside the region, most Maine trips start at Boston's Logan Airport or at Portland International Jetport. ... Plan a Maine tour with these beautiful road trips Revel in the beauty of the Pine Tree State at Maine's best state parks Enjoy the best of Maine's coast at these amazing beaches.

  27. Boston, MA to Portland, ME Bus

    The trip from Boston to Portland takes as short as 2 hours 15 minutes and could cost as little as $23.49. The first bus departs at 6:20 pm and the last bus departs at 6:35 pm. Greyhound offers daily bus rides from Boston to Portland. When traveling with Greyhound to Portland from Boston, expect free Wifi, power sockets, and a guaranteed seat ...

  28. Planning a New York to Maine Road Trip Itinerary

    This road trip is designed to go from New York City to Portland, Maine. However, if you want to include more stops between New York and Boston, you will also want to look at my New York to Boston ...

  29. Day Trips in Maine: 3 itineraries for eating, drinking and adventuring

    Jump to: Portland and Southern Maine| Bar Harbor and Coastal Maine| Rangeley and Western Maine. Maine is known as "Vacationland," and it really lives up to that name. Whether you want a day trip to the beach, a coastal hike or a mountain lake swim, Maine has it all. As you may have heard, we are known for our seafood, especially our lobster.

  30. Spirited 'Funny Girl' captures excitement of early musical theater

    On the heels of the show's recent Broadway revival, the Maine State Music Theatre has opened a spirited production of the classic musical on its home stage at the Pickard Theater on the campus ...