Things to do in The Berkshires

2 picks. Tours and experiences I'd book myself, with a note on why.

Where

All Caribbean Colorado Disney Hawaii Hudson Valley Italy New York City The Berkshires Wyoming

Type

Everything Food & wine History & culture Adventure & views Good with kids

Sort

The Clark Art Institute

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.

Check availability →

Guided Hike at Mount Greylock

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.

Check availability →