Now Is the Best Time for a Boston to Maine Road Trip!

New England never ceases to captivate all who visit. The best way to experience this region is to go on a road trip! Whether you’re a lifelong New Englander looking to escape hectic city life or a newcomer to the area, a Boston to Maine road trip is the perfect way to spend a few weekdays! Read on to discover the best sights to add to a Boston to Maine road trip itinerary.

Boothbay Harbor, Maine, is the ultimate New England destination and therefore an ideal place to end a Boston to Maine road trip. In fact, Maine coastal road trips including this charming small town are popular due to the area’s gorgeous rocky shores, plentiful amenities, and timeless appeal. Planning a trip to the Maine coastline is easy with our Boothbay Harbor Vacation Guide! The guide details Midcoast Maine’s best dining, shopping, and lodging selections. Download it today!

Stops to Make on a Boston to Maine Road Trip


Despite being a well-known destination in New England, Boston, Massachusetts, is a great city for beginning a great road trip. Here, a checklist should include riding the Swan Boats in the Boston Public Garden, visiting the Museum of Science, and going to Fenway Park for a baseball game. If interests lie more in academia, be sure to take a trip out to the MIT Museum in Cambridge. For a change of pace, the Boston Harbor Islands National Recreation Area is another great Boston attraction for nature lovers. It’s just a short ferry ride from Long Wharf in Boston.


After spending a day exploring Boston, be sure to make time for a quick stop in Salem, Massachusetts. This famous site of the 1692 Salem Witch Trials is just a 45-minute drive from Boston and has more to offer than interesting history. Do visit the Witch House, the former home of a trial judge, but also check out some of the town’s other landmarks such as the Stickworks Statues and the Salem Common park. Leave plenty of time to explore Maine, though, so a half-day is a reasonable amount of time to use for a visit to Salem.


The next must-see destination on a Boston to Maine road trip itinerary should be Portland, Maine. This celebrated place is the largest city in Maine and boasts a mixture of modern and traditional adventures. Here, spend a day exploring microbreweries, window shopping on Commercial Street, and touring art museums. If time outside is a priority, there are plenty of outdoor activities here. Portland also hosts numerous concerts and shows throughout the year, so be on the lookout for live entertainment.

Boothbay Harbor

Finally, end a Boston to Maine road trip in one of the most beautiful, historic, and traditional towns in Maine: Boothbay Harbor! There is no shortage of things to do for every type of traveler in this charming Coastal Maine destination. Love golf? There are several courses nearby. Need a little retail therapy? Stroll in and out of local shops and find handcrafted products. Hungry? There are a few fantastic restaurants just around the corner. Boothbay Harbor is also a boater’s paradise, so be sure to rent a boat or go kayaking. While here, you can even enjoy a day at the beach!

Stay at Coastal Maine’s Best Bed & Breakfast

After a tiring few days on the road, a multi-day stay at Boothbay Harbor’s best-kept secret, the Russell House Bed & Breakfast, will be a welcome luxury. This newly renovated bed & breakfast boasts a sophisticated, contemporary style unique to Midcoast Maine. The Russell House’s tranquil home-away-from-home setting is perfect for unwinding. Guests even savor a homemade breakfast each morning!

Our elegant and comfortable guest rooms are thoughtfully appointed with a queen or king bed, chic furnishings, a private bath, and hotel amenities. Two of our rooms also offer gas fireplaces for chillier nights!

Russell House Guest Rooms

After completing a Boston to Maine road trip, we know you’ll want to do it all over again. Be sure to visit the Russell House soon!