Things to do in The Berkshires

The Berkshires · About 3 hours per concert · $25 per adult

The Boston Symphony's summer home, where a picnic on the lawn with a concert is the classic Berkshires night; the 2026 season ran June 21 to September 2, and the 2027 lineup usually comes out in winter. Lawn seats are the cheapest way in; bring chairs and a picnic and arrive early for parking.

The Berkshires · Self-paced, 3 to 4 hours · $25 per adult

One of the biggest contemporary art museums in the country, in a restored 19th-century factory complex where the scale of the work is half the fun. Open year-round but closed Tuesdays, Thanksgiving and Christmas, and wear comfortable shoes because it's huge.

The Berkshires · Self-paced, 2 to 3 hours · $22 per adult

A world-class collection of Impressionist and old master paintings in Williamstown, set on 140 acres with walking trails and a reflecting pool. Open year-round, closed most Mondays outside July and August, and free for kids under 18 and on first Sundays from October to May.

The Berkshires · Self-paced, 2 hours · $25 per adult

The largest collection of Rockwell's original work, just outside Stockbridge, with his actual studio moved onto the grounds. Open year-round; the studio tours run on a limited spring and summer schedule, so check dates and book a slot ahead.

The Berkshires · About 2 hours · $22 per adult

Edith Wharton's 1902 house and formal gardens in Lenox, one of the prettiest stops in the county in summer and fall. The house is open daily May to October, weekends only from November to January 2, and closed January 3 to April, though the grounds are free year-round.

The Berkshires · About 2 to 3 hours · $20 per adult

A living history museum with the famous round stone barn, Shaker furniture and farm animals, about 10 minutes west of Pittsfield. It's open Friday to Sunday, 11am to 4pm, through November 29, then closes for winter until spring, so it's best May to October.

The Berkshires · About 2 hours · $150 per group

A private guided hike on the Greylock Glen trails at the foot of the highest peak in Massachusetts, with a local guide who picks the route and shows you spots like the old abandoned ski area. The price covers up to six people, so it's good value for a family or group of friends, and fall foliage weekends book up first.

The Berkshires · Full day · $124 per adult

The biggest ski area in southern New England, about 25 minutes from Lenox, with 45 trails and good night skiing. The season usually opens in late November; buy lift tickets online in advance, because weekend and holiday tickets can sell out at the window.