Berkshires: Places to Explore

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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... Read 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... Read more

  • 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... Read more

  • North Adams

    If you're looking for a Berkshires getaway that combines culture with outdoor fun (and a cool place to stay), put North Adams on your short list. Established as the military outpost Fort Massachusetts... Read more

  • Otis

    A more rustic alternative to Stockbridge and Lenox, Otis, with a ski area and 20 lakes and ponds, supplies plenty of what made the Berkshires desirable in the first placeā€”the great outdoors. Dining and... Read more

  • Pittsfield

    Pittsfield is a workaday city without the quaint, rural demeanor of the comparatively small Colonial towns that surround it. There's a positive buzz in Pittsfield these days, though. Symbols of resurgence... Read more

  • Stockbridge

    Stockbridge is the quintessence of small-town New England charm, untainted by large-scale development. It is also the blueprint for small-town America as represented on the covers of the Saturday Evening... Read 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... Read more

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