Places to Explore

• 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 leader... (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)

• 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), put North Adams on your short list. Established as the military outpost Fort Massachusetts... (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 place—the great outdoors. Dining... (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... (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... (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)