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4 Breathtaking Scenic Drives in Massachusetts

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berkshires massachusetts fall
The Berkshires are particularly lovely in autumn
Photo: Theo Dawson via Pixabay

Daydreaming about future road trips? Here are four routes you should consider if you’re planning a joy ride in Massachusetts later this year.


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Mount Greylock Scenic Byway

Journey the 17-mile route from Pittsfield to Adams, to enjoy panoramic views of Mount Greylock, the highest point in Massachusetts. Witness the Warm Memorial Tower, which commemorates the state’s fallen soldiers. Check out the historic Bascom Lodge, which overlooks the region that inspired some of Thoreau’s writings. Western Gateway Heritage State Park makes a pleasant detour if you want to squeeze in a bit of hiking.


Central Hills Loop

This 57-mile route starts and ends in New Salem, delivering delightful views of the water, forests, and rock formations. Quabbin Reservoir provides a picturesque backdrop for selfies. The historic covered bridge in Gilbertville makes another great photo op. Take to the trails at Bear’s Den to check out the falls and potentially see some local wildlife.


Cape Ann

Travel the Cape Ann route from Salem to Rockport to immerse yourself in views of the rocky Atlantic coast, lighthouses, and New England architecture. Halibut Point State Park is a good place to stop to snap some pictures. If visiting on a clear day, you’ll likely spot the Isles of Shoals just off the coast of New Hampshire, as well as Mount Agamenticus in Maine. Put Gloucester on the itinerary if you want to enhance your outing by taking a whale watching tour.


Northern Berkshires

Experience the vibrant fall foliage of rural Massachusetts when you take the Northern Berkshires route from Sunderland to Williamstown. This 53-mile-long path weaves through Savoy Mountain State Forest. You can also stop in North Adams to immerse yourself in the local arts scene; MASS MoCA and River Hill Pottery are two must-see spots. Learn more about the region’s Colonial period when you tour Historic Deerfield.

Need more destinations to add to your Massachusetts road trip itinerary? Cultivate a deeper appreciation for autos at these car museums. And check out this article to refresh yourself on one of the state’s safe driving protocols.


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