Luxury holidays in Berkshires

These forest-clad hills in western Massachusetts are Boston and New York’s very own back-to-nature bolthole. City-dwellers flock to the area, not only to ogle its natural beauty and stretch their legs in its great outdoors, but also to tap into New England’s rich creative seam – the place is crawling with artists, and, in the summer, its little colonial towns are alive with theatrical and musical events. It’s impossible to visit the Berkshires without stumbling upon fine art museums and galleries, world-renowned dance companies, celebrated symphony orchestras, cutting-edge drama troupes, landscaped gardens, and marvellous historic homes and museums. In the autumn, the foliage comes into its own, and the turning leaves paint smudgy streaks of russet and gold across the undulating landscape.

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Areas in the Berkshires

When to go

The Berkshires is a four-season destination. Summer brings in the theatre fans and nature lovers; autumn draws the daytrippers who come for the spectacular fall foliage; and winter marks the arrival of skiers and snowboarders. The mild (and potentially wet) spring may be the quietest time to go – but even in the busiest of seasons rural roads of the Berkshires can feel sleepy.

Getting there

  • Planes

    Direct flights from the UK arrive at Boston’s Logan Airport, two hours or so from the Berkshires, and New York City’s JFK Airport (three hours away). Internal flights from major US cities (as well as Toronto, Montreal and Amsterdam) touch down at Hartford‘s Bradley International Airport (, an hour and a half away by car.
  • Trains

    Amtrak’s ( Vermonter route snakes from St Albans to New York and Washington via Massachusetts and Connecticut. The Metro-North Railroad from New York ( runs from Grand Central to Waissac in Massachusetts, where a summer weekend express bus connects with Great Barrington.
  • Automobiles

    Although train and bus services around the Berkshires are pretty comprehensive, a car is a necessity for cruising the rural roads from hamlet to hamlet. Make sure you’ve pocketed the keys to a convertible in summer months, a 4x4 for winter. There are plenty of car hire outlets at Bradley International, NYC and Boston Logan.
  • Taxis

    Cabs are neither much user nor widely available on the country roads of the Berkshires, but Abbott’s Limousine and Livery Service (+1 413 243 1645; will take you anywhere your heart desires 24 hours a day – and will happily ferry you off you a guided tour of Berkshire County.