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.
Explore rarely seen areas of the house—including the 3rd floor—and learn about the servants’ life at Naumkeag during a Backstairs Tour offered at 9:30AM throughout the summer. Pre-registration is required as space is limited, so don’t forget to book your tickets well in advance.
Arriving later in the morning? Explore the story behind this modernist masterpiece on a Guided Garden Tour—included with General Admission—offered at 10:30AM, 11:30AM, and 2PM. If you’re interested in Naumkeag’s exterior architecture and how the house has evolved, plan your day around the 1PM Architecture Tour, also included with General Admission. Just don’t forget to register for either tour when you arrive on-site!
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
William Cullen Bryant Homestead
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 back South to the William Cullen Bryant Homestead.
Re-opening this summer for the first time since 2019, plan the weekend of your visit around one that offers a guided tour of the homestead. You’ll get a look inside William Cullen Bryant’s thoughtfully preserved country estate, where he spent his formative years and later returned for inspiration and retreat. Find period rooms filled with original furnishings, Bryant family artifacts, and sweeping views of the Westfield River Valley that helped shape his poetry and environmental values. Whether you’re a history enthusiast, literature lover, or simply someone who appreciates natural beauty and timeless stories, the Guided Tour offers an unforgettable experience.
After most of the morning and early afternoon spent exploring, make your way over to Pittsfield to visit some amazing museums and grab a bite to eat.
