Boston & Coastal Maine Road Trip – FAMILYTRAVELSUSA

EXPLORING THE CITY OF BOSTON ALONG WITH A SCENIC DRIVE TO BAR HARBOR MAINE

This trip combines the fun of being in the great city of Boston with a scenic road trip up the Maine coast as far north as Bar Harbor. Spend some time exploring all that the wonderful city of Boston has to offer before heading to Maine. In the summer, the streets come alive. On weekends, there are many street performers, especially in the area around Faneuil Hall. There is so much history in Boston, and kids love following the red brick Freedom Trail as you walk to various sites, including the Old North Church and the Copp’s Hill Burying Ground.

Before planning any road trips check the attraction or national park social media accounts and websites for the most current information. Vehicle reservations may be required for access in certain parts of the park like the Cadillac Summit Road. Some of the activities listed when this post was originally written may be unavailable.

Updated January 2025
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We love visiting Boston, and were fortunate to have family that lived in the historic North End for many years. One of the special things that my late Uncle Arthur shared with us was his love for feasts, but in particular the Saint Anthony’s Feast. Every summer at the end of August, the streets are filled with table after table of Italian favorites, including cannoli, zeppole and arancini for an entire weekend. My uncle would spend weeks preparing his favorite Italian dishes, and as the Grand Procession walked by his house, he would feed hundreds of parade participants. You can read Enjoy a Taste of Italy in Boston’s North End to see how we tried to recapture his Italian spirit on a recent visit. Don’t miss a chance for an authentic Italian meal in the North End at a place like the Daily Catch (tiny place and cash only). For dessert, stop by Bova’s Bakery on Salem Street, or Mike’s Pastry on Hanover Street, where there is always a line but it is worth the wait!

In addition to all the historical activities, other great ideas we recommend for families are riding the Swan Boats in Boston Public Garden, the Museum of Science, and the New England Aquarium. For kids 12 and older, the MIT Museum in Cambridge opened in a new, larger location in Fall, 2022. We enjoyed our visit to the original museum space and expect that the new facility will offer even more interesting exhibits. While in Cambridge, you can also visit the four museums that make up the Harvard Museums of Science and Culture. Of course, if you are a baseball fan, head out to historic Fenway Park to enjoy a game or take a guided tour to learn about the park’s history.

For a change of pace, after spending days in the city, take the ferry out to Boston Harbor Islands National Park. It’s just a short ferryboat ride from Long Wharf in Boston. There is lots of open space for kids to run around and explore all there is to see. The ferries generally run from October to May. Check out my 5 More Reasons to Visit Boston post for more ideas.

Hidden Gem - take the ferry to Boston Harbor Islands National Park.

Once you have finished your time in Boston, head up north on I95 through New Hampshire into Maine. There are many small, New England towns to stop in along the way, including Kennebunkport and Kennebunk (look for the famous Wedding Cake House). Continue on to Freeport, where you can shop at the flagship L.L. Bean Store, as well as some of the unique boutiques found in the area.

Cool sites on the road from Boston to Maine include the

As you continue on 95/295, take Route 1, which brings you over to the coastal town of Boothbay Harbor. This is a great place to spend the night. While the peaceful Sprucewold Lodge tucked away in the woods is no longer operating, there are plenty of options in town, including the Tugboat Inn right on the water.

The next day, break up the 3 hour drive to Bar Harbor by stopping at historic Fort Knox in Prospect, Maine. For a small fee, the kids can explore this historic fort, located on the banks of the Penobscot River. While the grounds are open all year, access to the fort is only available between May and October.

Fort Knox in Prospect Maine is a perfect stop on a road trip from Boston to Bar Harbor.

From Fort Knox, continue on to Bar Harbor, a great town with many activities to choose from. Of course, there are many choices for eating lobster and lobster rolls in this great town. If you want to learn more about the lobstering profession, jump on a tour boat right in the harbor. We choose to take a LuLu Lobster Boat Tour. The boat was small and it was a great way for the kids to learn about lobsters as they were pulled out of the water and to also see some of the local sea life!

Save 30% on hotels in Bar Harbor, Maine…a TripAdvisor Top 10 Summer Destination!

You could easily spend several days in nearby Acadia National Park. Cadillac Mountain is the highest point on the east coast and offers spectacular sunrise views (reservations required). The park has miles of carriage roads that are closed to car traffic, making it ideal for bike-riding. Sand Beach is a great place to visit, just remember that the ocean temperature is pretty chilly all summer. Be sure to stop at Jordan Pond House Restaurant to enjoy some of their famous popovers while sitting outside on the lawn and enjoying the view. Get the kids involved through the Junior Ranger Program and find other family-friendly activities. Be sure to read Cool Things to Do Around Bar Harbor Maine.

On either leg of the trip between Boston and Bar Harbor, stop at Red’s Eats in Wiscasset, Maine for one of their highly acclaimed lobster rolls. Expect a line at Red’s, open seasonally starting in mid-April. If that doesn’t work out, there are plenty of other popular places to find some of Maine’s best lobster rolls. If you still are craving lobster when you return to Boston, grab something from James Hook and Co. and eat by the water, or try Pauli’s in the North End.

Check out these related posts below for more information about Boston and Maine.

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