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The 5 Best Weekend Road Trips from Boston – Hotels Above Par

by Staff

One of the great things about Massachusetts is that from a city like Boston, you can reach dozens of beautiful weekend getaways within a few hours’ drive—and cruising there with a car from New England Audi Dealers is the best way to do it. To help get you started, we’ve rounded up our favorite Massachusetts road trips. 

Cape Cod

Cape Cod is a beloved summertime destination among Bostonians, but it’s just as lovely when crowds (and traffic) subside during the cooler months. The “arm” of Massachusetts offers miles of gorgeous Atlantic coastline, friendly mom-and-pop clam shacks serving hot and crispy fried seafood, and plenty of charming New England towns. Falmouth has a great aquarium and a lengthy bike path with several ice cream stops along the way. Provincetown, on the very tip of the cape, has its own spunky, high-energy culture if you’re looking for a social atmosphere with lively bars and oceanside inns. 

The Berkshires

If you want to drive further inland from Boston, travel about two hours west on the Mass Pike to The Berkshires: a lovely wooded and mountainous part of the state comprising over 30 small towns and dozens of cultural attractions. Music lovers must catch a performance at Tanglewood, a stunning indoor/outdoor performing arts venue with classical, family-friendly, and pop music performances throughout the year. Museums-goers can stop in at several well-maintained historic homes, including historic Deerfield Village, where you can travel back to colonial America, and world-class art museums such as The Clark Art Institute and the Norman Rockwell Museum. There are dozens of quaint inns, bed and breakfasts, larger hotels, and several luxurious retreats, including Miraval and Canyon Ranch in Lennox. 

Martha’s Vineyard

Get your sea legs for this road trip—getting to Martha’s Vineyard includes a car ferry, but once you’re there, you’ve escaped into a picturesque coastal getaway. The 87-square-mile island is home to stunning beaches, idyllic farms, and happening towns where you can find great seafood and international cuisines. The island is most crowded during the summer, but the shoulder season offers easier-to-secure restaurant reservations, great shopping, and outdoor activities like fishing, biking, horseback riding, and boating. 

Mount Greylock

The northwesternmost corner of the state is distinguished by Massachusetts’ Taconic mountains, of which Mount Greylock is the tallest peak at 3,489 feet. Hikers flock to the trailhead for the expansive view of western Massachusetts and New York from the summit (you can see up to 90 miles on a clear day), which is especially breathtaking during the fall foliage season. Campsites on the mountain offer one lodging option, but the neighboring towns of Adams and Williamstown are full of more amenity-rich places to stay. If you have time after your hike, the MASS MoCA art museum is certainly worth a visit. 


Drive north from the city and towards the Atlantic to reach the preppy seaside town of Newburyport on Massachusetts’ north shore. You’ll find a bustling downtown full of boutiques, unique food markets, restaurants, and quite a few day spas for relaxation. Or, head to the beach for lengthy coastal views and to watch birds, surfers, and parasailers on the waves. The town has an active events calendar throughout the year, so plan to visit during a festival, art show, or restaurant week to make the most of your trip. 

New England Audi Dealers x Hotels Above Par Partnership

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