Stephanie Gibson Lepore is the Copy/Research Editor of Country Living. She enjoys writing about a range of topics and making sure the facts are accurate. When she's not checking out the latest Instagram post from Merriam-Webster, you can find her hunting home decor at an antiques shop, reading WWII fiction in a sunny spot, cheering (loudly) for her football team, or planning her daughter's next birthday party (themes forever!). ","jobTitle":"Copy/Research Editor"}]},"publisher":{"@type":"NewsMediaOrganization","name":"Country Living","sameAs":["https://twitter.com/countryliving","https://www.youtube.com/c/CountryLiving","https://www.facebook.com/CountryLiving","https://instagram.com/countrylivingmag/","http://www.pinterest.com/countryliving/"],"logo":{"@type":"ImageObject","url":"https://www.countryliving.com/_assets/design-tokens/countryliving/static/images/logos/logo-jsonld.01b7535.png","width":312,"height":60},"parentOrganization":{"@type":"NewsMediaOrganization","name":"Hearst Corporation"}},"keywords":["content-type: Feature","locale: US","displayType: listicle"],"url":"https://www.countryliving.com/life/travel/g61975349/berkshires-travel-guide/","isBasedOn":"https://www.countryliving.com/life/travel/g61975349/berkshires-travel-guide/","isAccessibleForFree":"False","hasPart":[{"@type":"WebPageElement","isAccessibleForFree":"False","cssSelector":".content-container"}],"description":"The best restaurants, antique shops, museums, and more in Berkshire County, Massachusetts, a longtime bastion of the arts and outdoor recreation. ","author":{"name":"Sarah Zlotnick","url":"https://www.countryliving.com/author/228287/sarah-zlotnick/","@type":"Person","description":"
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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:
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
Nicole Franzen
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.
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.
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Stop in for a Swill
Courtesy Berkshire Mountain Distillers
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.
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.
Advertisement - Continue Reading Below
Drop Your Bags
Nicole Franzen
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
Courtesy Hammertown
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.
(Pictured: Dance pioneer Ted Shawn leading an outdoor class at Jacob's Pillow in 1954.)
Peek Behind the Prose
Barry Winiker//Getty Images
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.
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
Getty Images
Hoosac Valley Train Rides offers one-hour fall foliage rides between the Northern Berkshires Mountains in carefully restored mid-century railcars.
Sarah Zlotnick is the Lifestyle Director at Country Living, where she covers a little bit of everything—small towns, life in the country, and, her favorite, antiques. A research buff at heart, she loves a deep dive into the history of vintage finds and uncovering the reasons behind old-as-time traditions.
Stephanie Gibson Lepore is the Copy/Research Editor of Country Living. She enjoys writing about a range of topics and making sure the facts are accurate. When she's not checking out the latest Instagram post from Merriam-Webster, you can find her hunting home decor at an antiques shop, reading WWII fiction in a sunny spot, cheering (loudly) for her football team, or planning her daughter's next birthday party (themes forever!).
Fact-checked by Stephanie Gibson LeporeCopy/Research Editor
