History, houses and harbors
Your road trip will begin in Boston. Walk the Freedom Trail to discover more about U.S. history and the American Revolution. Reviewers on TripAdvisor say the 2.5-mile trail is easy to follow and call it “captivating” and “an unparalleled experience” for history lovers. There are a ton of other things to do in the city: visit Fenway Park, the home of the Red Sox; see incredible paintings at the Museum of Fine Arts; or wander through the lovely Public Garden.
When you’re ready, get on the road and head about an hour and a half south to Newport, RI. The main draw here is the Newport Mansions — opulent “summer cottages” that date from the Colonial Era to the Gilded Age. The most famous (and most jaw-dropping) is The Breakers, which you can visit to get an insight into the lives of the mega-wealthy Vanderbilts. Google reviewers call the mansion “breathtaking” and the history “fascinating.” Many of the mansions are situated along the spectacular Cliff Walk, a 3.5-mile stroll that combines history and coastal views.
Next, you’ll drive an hour west to Mystic, CT. The charming town is full of Colonial-era architecture, and Mystic Seaport is the perfect place to learn what a 19th-century seafaring village was like. Several reviewers on TripAdvisor say that their favorite part was the reconstructed working shipyard. Mystic is a great place to try some seafood, too. Check out the Oyster Club, where the flavors are “unreal,” according to one reviewer.
Peaks and parks, brews and beaches
From Mystic, drive inland across the rolling hills of the Berkshires in Western Massachusetts and through the Green Mountains to Burlington, VT. You’ll pass through lovely Waterbury on your way. If you have time, consider taking a detour on the Green Mountain Byway to the famous Stowe, one of the top places to see fall foliage in America. Stay overnight in Burlington to enjoy one of the many breweries there. Local Reddit users in the r/burlington forum love Queen City and Burlington Beer Co.
When your head’s cleared, drive across the state line into New Hampshire and explore the White Mountains. The most famous route in the region is the Kancamagus Highway, where the fall foliage views are spectacular. If you want to stretch your legs, check out one of AllTrails’ top-rated hikes in the area. The challenging Welch-Dickey Loop Trail has more scenic fall colors, according to reviewers, and the relatively short Mount Willard Trail has a great payoff in terms of views.
The final major stops on this trip are in Maine at Acadia National Park and Bar Harbor. The park stretches across 50,000 acres; if you’re unsure where to start, the National Parks Service suggests driving the 27-mile Park Loop Road for the best views in the area. Stay overnight in the delightful gateway town of Bar Harbor and enjoy some of the freshest seafood in the U.S. From here, it’s a glorious five-hour drive back to Boston.
