The Berkshires

An arts-loving hill region in western Massachusetts, with the Tanglewood music festival in summer, fall foliage in autumn, and the distinctive Norman Rockwell Museum, MASS MoCA and the Clark Art Institute.

The Berkshires occupy Berkshire County at the far western end of Massachusetts, between the Hudson Valley and the Connecticut River Valley – a landscape of rolling low mountains, lakes and New England towns. Since the late 19th century it has been a summer retreat for wealthy Bostonians and New Yorkers, and the Gilded Age left behind a wealth of grand estates. This destination uses Lenox as its base. To the south are Tanglewood, Edith Wharton's home The Mount, and Shakespeare & Company; Stockbridge, with the Norman Rockwell Museum, the Naumkeag estate and the Main Street that Rockwell painted; and, at the southern end, Great Barrington, Monument Mountain and Bash Bish Falls. In the center, Pittsfield has Hancock Shaker Village and Arrowhead, where Herman Melville wrote Moby-Dick. In the north, North Adams and Williamstown are home to MASS MoCA (the Massachusetts Museum of Contemporary Art), the Clark Art Institute and Mount Greylock, the highest peak in Massachusetts – worth a full day. Summer (July–August) is the cultural season, with performances at Tanglewood and the Jacob's Pillow Dance Festival; fall foliage is best from late September to mid-October, and the Mohawk Trail drive and the summit of Mount Greylock are leaf-peeping hotspots; in winter you can ski at Jiminy Peak, though many estates and historic homes close for the season. The region is about 2.5 hours' drive from Boston and about 3 hours from New York City; the nearest major airport is Albany. Local public transportation is scarce, so you'll essentially need a car. Allow 3–4 days, and book ahead – lodging is tight during summer performances and on fall weekends.

Top sights

Where to eat

Itineraries