A Very Country Guide to The Berkshires
There’s not too many places in North America that offer the perfect mix of fresh air, small town living, and top-shelf food and entertainment. You could head to New York’s North Fork, or traipse around Canada’s Prince Edward County, but, come fall, there’s nothing quite like The Berkshires. Nestled along the western edge of Massachusetts, Berkshire County—and the 30(!) small towns within its midst—shine bright each autumn with famous estates, farm-to-table fare, and ample foliage.
While the modern art museums are world-class, and the wellness offerings are delightfully New Age (sound bath, anyone?), those seeking a more backroads experience in the Berkshires will certainly find it amongst the farmstands, historic B&Bs, antique halls, and hiking trails. Ahead, we’re sharing our decidedly country spin on a weekend in Berkshires, including favorite spots for shopping, food and drink, and more. But first, before you head out, a lesson in pronunciation: While locals seem split between “Berk-sherrs” and “Berk-sheers,” the only time to use “Berk-shiyer” is in reference to the county in England.
More of our favorite small town fall excursions across the continent:
16 Ways to Spend the Perfect Fall Day in Sperryville, Virginia
This Quaint Vermont Town Should Be at the Top of Your Fall Travel List
America’s Next Great Antiquing Destination is this Tiny California Town
Rise and Grind
Family-owned No. Six Depot Roastery brews perfectly balanced pour-overs in a circa-1834 train station, while Marjoram & Roux delights baked good enthusiasts with creative pastries (banana granola scones!) in a quaint café.
Celebrate the Scenery
The first Sunday of October marks the annual fall foliage parade in North Adams. Post-revelry, the changing leaves are best taken in at the scenic Olivia’s Overlook (pictured) or on a winding drive to the summit of Mount Greylock, the Bay State’s tallest peak.
RELATED: 55 of the Best Small Towns in the U.S. for Fall Foliage
Brake for Antiques
Fans of retro whimsy and nostalgia should explore every corner of 7,000-square-foot Berkshire Great Finds, while more serious antiquers will uncover priceless treasures at Samuel Herrup and Susan Silver Antiques.
RELATED: 100+ Best Places to Shop for Vintage and Antiques Online
Step Through Time
Living history museum Hancock Shaker Village puts the high-quality craftsmanship of the Shakers on full display. The Norman Rockwell Museum is home to 998 original works by the prolific The Saturday Evening Post illustrator.
Stop in for a Swill
The small-batch spirits at Berkshire Mountain Distillery include earthy corn whiskeys and smoky oak rums (pictured), while certified B-Corp Berkshire Cider Project specializes in sustainably-made dry and sparkling blends.
RELATED: What’s the Difference Between Apple Cider and Apple Juice?
Do Dinner Right
Widow Bingham’s Tavern at the historic The Red Lion Inn serves hearty soups and sandwiches in cozy quarters. Larger tables should be booked in advance for the always-packed Prairie Whale, a lively come-as-you-are establishment focused on inventive seasonal fare.
Drop Your Bags
For an elevated bed-and-breakfast experience, reserve a room at The Inn at Kenmore Hall (pictured), which is run by a former J. Crew exec, a restauranteur, and their sweet pup Dutch. Also an option: the wonderfully unfussy Granville House, which is owned by two Gramercy Taverns alums.
More in the market for a bespoke rental? Many consider the town of Great Barrington to be the area’s up-and-coming cultural center.
Explore the Stores
The home goods at Great Barrington’s Hammertown are perfectly fit for a farmhouse. Berkshire Pottery (above) has been slinging handmade ceramics since 1960, and T.P. Saddleblanket brings Western style east with an eye-catching array of blanket coats and embellished leather belts.
Indulge in the Arts
The Jacob’s Pillow Dance Festival and Williamstown Theater Festival draw art-lovers en masse come summer, but fall visitors can still book tickets for the Barrington Stage Company, which serves as somewhat of a proving ground for new Broadway musicals.
(Pictured: Dance pioneer Ted Shawn leading an outdoor class at Jacob's Pillow in 1954.)
Peek Behind the Prose
Herman Melville penned Moby Dick at his open-to-the-public home, Arrowhead. Edith Wharton’s grand Lenox estate, The Mount (pictured), now hosts author lectures.
RELATED: The Best Celebrity-Narrated Books on Audible
Eat Fresh
At North Plain Farm, Sean Stanton offers grass-fed meats, pasture-raised eggs, and other local food products at his self-serve on-site farm store. For delicious sandwiches and to-die-for cheese plates, head to Rubiner’s Cheesemongers.
Ride the Rails
Hoosac Valley Train Rides offers one-hour fall foliage rides between the Northern Berkshires Mountains in carefully restored mid-century railcars.
RELATED: Amazing Fall Foliage Train Rides With Truly Stunning Views
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