Weekend in the Berkshires

Want to get away for the weekend? We’ve arranged a sample itinerary in the Berkshires featuring history, scenic vistas, and a cozy inn.

Naumkeag

Before Your Trip

If you’re coming from out-of-town for your weekend in the Berkshires, book your stay in The Guest House at Field Farm in Williamstown which offers an authentic mid-century-modern Bed & Breakfast. The house and landscape feature an unparalleled view of Mt. Greylock, Massachusetts’ highest peak, and is a refreshing change from your usual bed & breakfast.

Day One

Start your weekend at Naumkeag, a public garden and historic home in Stockbridge.

This Gilded Age estate is renowned for its elegant gardens and rare Berkshire “cottage.” In 1884, Joseph Choate—a prominent New York attorney and U.S. Ambassador to Great Britain—and his wife, Caroline, hired the famous architectural firm of McKim, Mead & White to design a summer retreat. The result was a 44-room shingle-style home, where several generations of the Choate family lived until daughter Mabel Choate bequeathed it to The Trustees in 1958.

Carve out time to explore the 8 acres of formal gardens created by Mabel Choate and noted landscape architect Fletcher Steele. Take in the famous Blue Steps and walk through the other garden “rooms” each with a beauty that reveals the playful, inventive spirit of collaboration between Ms. Choate and Mr. Steele, which played out over 30 years.

Bartholomew's Cobble

After taking it all in at Naumkeag, head south about 30 minutes to Bartholomew’s Cobble, stopping for lunch in Great Barrington along the way.

Bartholomew’s Cobble is named for its two rocky knolls—or “cobbles”—rising above the Housatonic River. Hurlburt’s Hill, the property’s highest point, rises 1,000 feet to a 20-acre upland field on the Massachusetts-Connecticut border that offers panoramic views northward up the Housatonic River Valley. Boasting an enormous variety of woodland flowers and fern species, the Cobble’s amazingly diverse flora earned it a National Natural Landmark designation in 1971.

Walk five miles of trails and discover the diversity of this landscape—open fields, transitional forests, freshwater marshes, a pair of small caves, and more. Along the way, you’ll find one of North America’s greatest diversities of fern species as well as one of the largest Cottonwood trees in the state. Paddle the Housatonic River, tour the on-site natural history museum, and make sure you return between mid-April and the end of May, when the wildflowers reach peak bloom across the property’s 329 acres.

Field Farm

Mountain Meadow trail with Berkshire Hill views

Mountain Meadow Preserve

Day Two

Out-of-town visitors can wake up to a stunning view at The Guest House at Field Farm. But even if you’re staying elsewhere, spend the morning hiking around the property, while taking in art and nature. After lunch in one of the many surrounding towns, make your way further North to Mountain Meadow Preserve.

Rising in elevation from 690 feet at the Williamstown parking lot to more than 1,100 feet, Mountain Meadow Preserve provides multiple natural habitats and rich ecology: it’s home to bears, coyotes, bobcats, fox, and deer as well as wetland amphibians and numerous small mammals and reptiles. Meanwhile, the meadow’s mix of flowers and grasses, including aster, little bluestem, and fringed gentian, attracts a variety of butterflies. From the meadow, peek through a forested ridge and enjoy mountain vistas across 180 acres.

After most of the morning and early afternoon spent exploring, make your way over to North Adams to visit some world-class museums and grab a bite to eat.

 

 

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