Places to Explore In The Berkshires

Discover the best places to explore in The Berkshires with curated recommendations from our travel experts.

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...

  • 6 Restaurants
  • 1 Hotels
  • 14 Things To Do

Hancock

Tiny Hancock, the village closest to the Jiminy Peak ski resort, really comes into its own in winter, though it's also a great base for...

  • 0 Restaurants
  • 2 Hotels
  • 1 Things To Do

Lenox

The famed Tanglewood music festival has been a fixture in upscale Lenox for decades, and it's one of the reasons the town remains fiercely popular...

  • 9 Restaurants
  • 5 Hotels
  • 10 Things To Do

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...

  • 7 Restaurants
  • 2 Hotels
  • 6 Things To Do

Otis

With a ski area and 20 lakes and ponds, Otis supplies plenty of what made the Berkshires desirable in the first place: the great outdoors...

  • 0 Restaurants
  • 0 Hotels
  • 0 Things To Do

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...

  • 6 Restaurants
  • 1 Hotels
  • 9 Things To Do

Stockbridge

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

  • 4 Restaurants
  • 2 Hotels
  • 7 Things To Do

Williamstown

Williamstown is largely built around the prestigious Williams College, a smallish but verdant campus bisected by Route 2. Williams is one of the "Little Ivies,"...

  • 6 Restaurants
  • 3 Hotels
  • 7 Things To Do

Explore The Berkshires

Sights 34

Shopping 12

Performing Arts 8

Restaurants 40

Hotels 16
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