Trip IdeasBerkshires Places
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Great Barrington
The largest town in South County became, in 1781, the first place in the United States to free a slave under due process of law and was also the birthplace, in 1868, of W. E. B. DuBois, the civil rights... (more) -
Hancock
Tiny Hancock, the village closest to the Jiminy Peak ski resort, comes into its own in winter. It's also a great base for outdoors enthusiasts year-round, with biking, hiking, and other options in summer... (more) -
Lee
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Lenox
The famed Tanglewood music festival has been a fixture in upscale Lenox for decades, and it's a part of the reason the town remains fiercely popular in summer. Booking a room here or in any of the nearby... (more) -
North Adams
If you're looking for a Berkshires getaway that combines culture with outdoor fun (and a cool place to stay as a bonus), put North Adams on your short list.... Established as the military outpost Fort Massachusetts... (more) -
Otis
A more rustic alternative to the polish of Stockbridge and Lenox, Otis, with a ski area and 20 lakes and ponds, supplies plenty of what made the Berkshires desirable in the first place—the great... (more) -
Pittsfield
A mere agricultural backwater at the time of the American Revolution, the seat of Berkshire County grew steadily throughout the 19th century into an industrial powerhouse of textile, paper, and electrical... (more) -
Stockbridge
Stockbridge is the quintessence of small-town New England charm, untainted by industry or large-scale development. It is also the blueprint for small-town America as represented picture perfectly on the... (more) -
Williamstown
When Colonel Ephraim Williams left money to found a free school in what was then known as West Hoosac, he stipulated that the town's name be changed to Williamstown. Williams College opened in 1793 and... (more)
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