Weekend in the Berkshires

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


Day One

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

Naumkeag — Experience Gilded Age style and splendor at this marvelous estate renowned for its elegant gardens and rare Berkshire “cottage”.

This 48-acre architectural masterpiece is, at its heart, a family home. 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.

When you visit this National Historic Landmark, carve out time to explore the superlative gardens created by Mabel Choate and noted landscape architect Fletcher Steele. Take in the Blue Steps, a series of deep blue fountain pools, flanked by four flights of stairs and a grove of white birches. Elsewhere walk through the stunning beautiful Afternoon Garden, Tree Peony Terrace, Rose Garden, Evergreen Garden, and Chinese Garden, each of which evinces beauty while revealing the playful, inventive spirit of collaboration between Ms. Choate and Mr. Steele, which played out over the span of 30 years.

While on site, stop for some refreshment at the new café, where you can find beverages, charcuterie boards with locally prepared food items, and sweet treats.

Boulder at Bart's Cobble

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.

Explore 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.

The view from Field Farm

Mountain Meadow trail with Berkshire Hill views

Mountain Meadow Preserve

Day Two

Wake up at the stunning Field Farm in Williamstown and spend the morning hiking around the property, while taking in art and nature. After lunch in a surrounding town, 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 a morning 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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