The Best Boston to Bar Harbor Maine Road Trip

The best time of the year is slowly approaching, especially if you love anything fall related: pumpkin spiced chai lattes, apple cider donuts, and sweater weather, autumn season. Last year, I jetted off on a New England fall road trip and it has become one of my favorite trips of all time. I love sharing my travels, and this one is no different. Here I have come up with a great way to explore what Maine has to offer, starting off with Boston and then heading off to Portland, Maine then to Bar Harbor and then, lastly, to Acadia National Park and witness the beautiful fall foliage.

Where is Maine?

Maine is a component of New England. New England a region in the Northeastern United States made up of 6 states: Maine, New Hampshire, Vermont, Massachusetts, Connecticut and Rhode Island. These states are so close in proximity, and easily accessible with a car, which makes New England the perfect place for a fall road trip!

When To Go?

If you’re looking for peak foliage make sure to look into foliage trackers, which give you a general idea of when to visit, like this one. I will say this, use these as a general guide. Alex and I went to New England after “peak foliage” and there was still plenty of beauty to see. There were PLENTY of beautiful trees with gorgeous colors. Good rule of thumb.

How To Get There?

You can access New England from any of the airports in the six states:

  • Boston Logan International Airport – Massachusetts
  • Bradley International Airport – Connecticut
  • Rhode Island T.F. Green International Airport -Rhode Island
  • Burlington International Airport – Vermont
  • Portland International Jetport – Maine
  • Manchester Boston Regional Airport – New Hampshire
  • Albany International Airport – New York (technically not part of New England, but it’s right outside it)

Depending on where you’d like to start your journey, you have many options to choose from. As I was researching flights though I noticed flights were slightly cheaper when you flew in and out of Boston. This makes sense as it’s a bigger airport, something to keep in mind. And with that we start our adventure in Boston!

Boston to Bar Harbor Maine Fall Road Trip

I will say the best way to get around New England will be by car, so renting one will be a must. Now don’t worry if you don’t like driving in a busy metropolitan city like Boston, the plan is to briefly be in the city. Now the plan is to ultimately make our way to Bar Harbor Maine. However, it wouldn’t be a fun New England road trip without making some quick pit stops in between Boston to Bar Harbor Maine.

Boston to Portland, Maine

Now, before we make our way to our first destination in Maine, I figured we can add a quick pit stop. Our first stop is only about 40 minutes away from the Boston Logan airport, to Salem. Now you can skip this stop all together and head straight to Portland instead. However, if you do that you’d be doing yourself a disservice and never find out there’s more adventures from Boston to Portland, Maine than you can imagine.

Salem, Massachusetts

Any Hocus Pocus fans?! What better way to start a fall road trip than by visiting Salem, Massachusetts? Check out some spooky ghost tours, rejoice in all things Halloween, visit all the sites where the movie was filmed and learn about the town’s history!

I recommend spending at least one day in Salem and really taking it in. I’ve only been to Salem once before, but only for half a day. We checked out the history and hauntings of Salem on a guided walking tour. We learned about the town’s history and spooky sightings, which I highly recommend. There’s a variety of tours you can do even some at night. The town rejoices in Halloween festivities, so visiting Salem during October is such a unique and wonderful experience you have to check out.

New England Fall Road Trip: Portland, Maine

After you’ve spent a day in Salem, head north to Portland, Maine! At about a little over an hour and a half, you’ll find this cool, trendy town, which happens to be the largest city in Maine. Spend a day in Portland and check out Old Port, the heart of the town. This downtown neighborhood is filled with many nick nacks left and right. The city preserves the town’s history, cobblestone streets, wharf and 19th century warehouses, while giving it a modern day twist.

If you’re not allergic to seafood, take advantage of your one night in Maine and eat some good seafood! Check out Luke’s Lobster Portland Pier, you can’t go to Maine and not eat seafood (unless you’re allergic). Afterwards, walk around downtown, enjoy the ambiance and uniqueness that makes Portland, well, Portland. Heads up, Portland is a harbor town, which can be busy when cruise ships dock, so if you find any restaurants you know you definitely want to check out make, reservations ahead of time.

Now you can’t go to Maine and not go light house sighting! Or maybe you want more of a quiet experience in Maine? At only about 30 minutes outside South Portland, you’ll find Cape Elizabeth, a small but beautiful town home to the famous Portland Head Lighthouse. Definitely make a pit stop here if you can. The area is beautiful, quiet and peaceful. It’s a wonderful place to stop and enjoy the sunset after a long day.

Portland to Acadia National Park

Next stop on our New England fall road trip, we make our way to Acadia National Park and witness some breathtaking fall foliage. It’s about a 3 hour drive from Portland to Acadia National Park, so you’ll need to need hit the road early.

Acadia National Park

This place had been on my bucket list for awhile now, and for good reason too! I once heard about Cadillac Mountain the first time I visited New England. Once I had heard about it, I wanted to jet off and experience it first hand. Now, if you’re not aware of what I’m talking about, I’m here to let you in on the number one thing to do in Acadia National Park.

From October to March, it’s said Cadillac Mountain in Acadia National Park is the first place the sunrise breaks through in the US. Be prepared to wake up super early in the morning (and bring a blanket) to welcome the sun. You’ll need to make a reservation at Recreation.gov. Once you look up Cadillac Summit, you’ll be faced with two options, daytime and sunrise. Opt for the sunrise option, you’ll need to purchase a $6 reservation (1 reservation ticket per vehicle) along with your national park fee to hit the summit. I recommend you get there EARLY. It fills up quickly. Plus, you’ll want to make sure you get a good spot.

Acadia National Park Fall foliage

The great thing about visiting Acadia during the fall is that you get to witness the beautiful fall foliage. As you can see the park does not disappoint. There are so many spots worth checking out when you visit. You can literally walk around anywhere and witness the gorgeous fall foliage Acadia National Park has to offer. Below are some of my favorites spots:

Bar Harbor

Do you ever walk into a small town and get major Gilmore Girl vibes? If not, stop by Bar Harbor, right outside of Acadia National Park. This cute little town is filled with plenty of mom and pop shops and picturesque photo ops. Here are some cute shops worth checking out next time you visit:

  • Sunny Street Cafe: Check this family owned cafe out for breakfast or lunch!
  • Acadia Perk: Anyone a Friends fan? Check out this cute coffee shop in the heart of Bar Harbor. They have a delicious blueberry macchiato, a Bar Harbor original, according to their website.
  • CJs Big Dipper: Enjoy some yummy ice cream and walk around the square. After all, ice cream tastes better in the cold 😉
  • The Independent Cafe: Check out this laid back cafe, a great place for sandwiches, coffee and anything in between
  • Bar Harbor Popcorn: Get some popcorn for your loved ones back home from Bar Harbor popcorn.

It goes without saying I love checking out small towns, but what I enjoy the most is supporting small businesses. After all, when you support a small business you’re supporting a dream.


Check out my other New England posts for more fall inspiration here!


Map of Attractions

Trip map created using Wanderlog, a travel planner on iOS and Android

In Conclusion…

Boston to Bar Harbor Maine, Portland to acadia national park, New England fall road trip, boston to portland maine, acadia national park fall foliage

Whether you make your way out to Boston, Bar Harbor, Maine or Portland, Maine from Boston or Portland to Acadia National Park rest assured this travel guide has got your back! Now, if you’re limited on time, at least make your way out to Acadia National Park, and witness the foliage and experience Cadillac Mountain for yourself!!! If I had to name one thing as my favorite thing to do on this road trip it would hands down be Cadillac Mountain. There’s nothing like it, so do yourself a favor and check out New England this fall!