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Berkshires, Massachusetts

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Personality Types that Like it Best

Did You Know … ?

  • The movie, “Cider House Rules” (1999), was filmed at Ventfort Hall, the Museum of the Gilded Age, in Lenox.
  • Folk singer Arlo Guthrie wrote “Alice’s Restaurant” based on a true incident that occurred in Stockbridge (1965).
  • Crane and Company in Dalton makes the cotton-based paper used in printing U.S. currency.
  • Jacob’s Pillow in Becket was America’s first dance school (1933).
  • The Williamstown Theatre Festival was the first summer theater to receive a Tony for outstanding regional theater (2002).

Two faces

Berkshire is the name of a county in western Massachusetts. It extends north to south from the Vermont to Connecticut borders, and to the west, it abuts New York state. The Berkshires is the common name for the county’s highlands, more properly termed the Berkshire Hills.

The highest peak in the county, and in the state, is Mount Greylock at 3,491 feet. It is one of several peaks that, along with Berkshire lakes and rivers, provide the settings for a wide range of outdoor activities in all seasons. The region is particularly well known for its ski resorts, but in other seasons, outdoorsy types flock to the Berkshires for cycling, fishing, hiking, kayaking, whitewater rafting and even the chance to ride a zipline or two. Depending on season, ice climbing and rock climbing are on offer, as well.

Enjoying the outdoors also translates into scenic drives, particularly in the autumn as trees change colors. The whole state is known for fall foliage viewing, but the Berkshires have the advantage of viewing points provided by its hills and valleys.

The Berkshires are a destination with two faces. Obvious physical charms and serenity gained the Berkshires a reputation as an idyllic playground, but those same characteristics attracted creative personalities over an extended time period. As a result, the Berkshires are a culture center in their own right, without the anchor of a major city.
Tanglewood, between Lenox and Stockbridge, has been the Boston Symphony Orchestra’s summer home since the 1930s. Also since the 1930s, the Jacob’s Pillow dance school has been situated on a farm at Becket.

Furthermore, summer theater is big here, drawing established actors as well as aspiring talent to annual festivals. Museums include the Massachusetts Museum of Contemporary Art (MASS MoCA) on a campus of renovated 19th century factory buildings.

Artists, writers — and the wealthy in the Gilded Age — came here to live, too. Norman Rockwell, and writers Nathaniel Hawthorne, Herman Melville and Edith Wharton had Berkshires homes. The homes and/or studios (except for Hawthorne’s) are tourist attractions. Wharton’s home, the Mount, is in fact one of the area’s Gilded Age estates.

Things to do for Venturers

  • Compete in the Berkshire Marathon over Memorial Day weekend.
  • In Charlemont, take a zipliner’s canopy tour across the treetops.
  • Also in the Charlemont area, choose a whitewater rafting tour, or a rock climbing excursion, or both.
  • Take a class in fusing glass at 413 Glassworks in Cheshire. Tour the glass studio and shop.
  • Ride a mountain bike, or hike, the extensive trails in Pleasant Valley Wildlife Sanctuary, a 1,300-acre wilderness. The trails vary in difficulty levels.
  • Bring friends to compete in the early autumn Annual Great Josh Billings RunAground Triathlon. It’s a team effort, with one member cycling, one canoeing (or stand-up paddling) and a third running.

Things to do for Centrics

  • Massachusetts’ 63-mile Mohawk Trail, America’s first scenic driving route, traverses the northern Berkshires. Drive it. Better yet, drive it in autumn for the foliage colors.
  • Listen to the Boston Symphony Orchestra on a summer weekend at Tanglewood near Lenox. Bring a picnic supper to enjoy on the lawns while listening.
  • Cycle the 11-mile Ashuwillticook Rail Trail, or in winter use it for cross-country skiing.
  • Focus on modern art at the Massachusetts Museum of Contemporary Art (MASS MoCA) complex in North Adams. Set on a 13-acre campus, it is America’s largest center for contemporary art.
  • Kayak on the Deerfield River.
  • Get married on the grounds of the Hancock Shaker Village in Pittsfield. Or, if marriage is not in the offing, tour and enjoy the setting.

Things to do for Authentics

  • See a production at the Williamstown Theatre Festival. There are several other choices for theater as well. Or, attend the summertime Jacob’s Pillow Dance Festival; if the timing is wrong, other options include a guided tour of the school (a designated National Historic Landmark), dinner at the Pillow Cafe and more.
  • Visit homes of interest, such as Edith Wharton’s grand estate, the Mount, at Lenox or Herman Melville’s Arrowhead at Pittsfield.
  • Peruse the largest collection of Norman Rockwell artwork at the Norman Rockwell Museum in Stockbridge. Visit his studio on site, as well.
  • Fish for bass on the 125-acre private lake at the Berkshire Fishing Club — no license required.
  • Make the Berkshires your ski destination. There are more than a dozen ski areas.
  • Shop, or just look, at the summertime Sheffield Antiques Show. Or, choose the Berkshire Crafts Fair, noted for the high quality of the goods on offer, in Great Barrington, also in summer.

Additional Resources

For more information, consult the Massachusetts Office of Travel and Tourism at