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Weekend in the Berkshires

Thinking about a weekend trip from New York City to the Berkshires? We’ve put together a sample itinerary featuring Massachusetts history, scenic vistas, and a cozy inn.

Thinking about escaping New York City to head to the Berkshires?

From Williamstown to Sheffield, The Trustees invites you to 14 unique places in the Berkshires. A weekend spent visiting any, or all of them is sure to help you refresh your mind and spirit.

Do you have the American Wing of the Met memorized? Then you’ll want to visit Naumkeag in Stockbridge, a Gilded Age cottage with lush grounds designed by Fletcher Steele that will truly lead you down the garden path.


Visit Naumkeag


A soaring peak overlooking the Housatonic Valley

Are you the person on the subway escalator that breezes by everyone standing on the right? Then trails and views on Monument Mountain will challenge even the most experienced uptown hikers.

Monument Mountain

Are you always looking up in awe at the stone architecture of Manhattan? Then the spectacular geological sights at Bartholomew’s Cobble might be just the thing for you.

If these options sound like the makings of a great adventure, come stay with us, and discover the Berkshires all over again.

Book your stay at Field Farm Guest House, in Williamstown MA, an authentic mid-century-modern Bed & Breakfast.

Berkshires Weekend


Bartholomew's Cobble

The view from the Guest House at Field Farm

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