Berkshires: Places to Explore

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... Read more

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

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

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

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... Read more

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 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

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