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Berkshires Travel Guide

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The Berkshires is the nickname for Berkshire County the western-most region of Massachusetts that borders on Connecticut. The countryside is dappled with charming villages, verdant farms, thick forest and crumbling stone walls. Travel to the Berkshires for a lovely weekend getaway or romantic summer retreat. The Berkshires has long been a haven for artists, musicians, writers, and revolutionary thinkers who’ve fled the claustrophobia of New York City or Boston to set up sanctuaries in the serene countryside. Visit the Berkshires to discover that a bohemian atmosphere persists in the folk festivals, bookshops, farmers markets and art galleries that grace the winding country roads. Check out the Travel + Leisure Berkshires travel guide to find the best hotels, restaurants and sights.

Things Not to Miss in the Berkshires

• Catch a performance by the Boston Symphony Orchestra at Tanglewood
 • Peruse the Norman Rockwell Museum, MASS MoCA and Clark Art Institute
 • Watch a dance performance at Jacob's Pillow
 • Visit the Hancock Shaker Village to see a living slice of American history
 • Hike up Mount Greylock
 • Stop in Great Barrington to do an afternoon of shopping
 • Drive the Mohawk Trail in autumn to see the leaves change

When to Go to Berkshires

Berkshires travel is excellent year-round, since there are always seasonal activities to tempt visitors. The height of the tourist season is the summer (June to August) when city-dwellers from Boston and New York make the 2.5-hour drive into the countryside. There are many wonderful summer festivals that visitors won’t want to miss, like the Williamstown Theater Festival and the Tanglewood summer music series. In fall, when the weather cools down, travelers can watch the autumn leaves change, and winter is perfect for skiing.

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