In less time than it would take to read Edith Wharton's Ethan Frome, you could be having your own charmed experience in the Berkshires. While the masses flock to the Catskills, an upstate region that’s become a satellite community for Brooklyn weekend expats, you could head east of the Hudson River to the Southern Berkshires destination: Great Barrington (just 20 minutes south of Wharton’s “first real home” in nearby Lenox). The quaint brick town is just as charming as fictitious Starkfield, but with an artful undercurrent and cultural relevance that’s worthy of its two-and-a-half-hour-drive from New York. “Part of the town’s appeal is that it’s not too reachable—getting here requires logistics and planning, so there’s a sense of successfully preserving what makes this place so special,” local travel consultant Rebecca MacGregor tells Vogue.

While The Berkshires have persisted as a haven for nature-lovers and artists alike, in the last few years, it’s developed a new draw: young New Yorkers. With a slew of new businesses and improvements to existing cultural institutions, Great Barrington has become one of the most popular destinations in the highlands of Massachusetts. The town is pulsing with a revival that not only evokes appreciation for its long-standing appeal, but also an evolution that’s representative of our farm-to-table loving, environmentally conscious generation. It’s so charismatic, you might find yourself lured to the real estate listings window as you sip a fresh cup of spiced apple cider from the farmers market on a crisp day. According to the Berkshires’ own premier real estate agency, the age of metropolitan couples that flock exponentially to the Great Barrington area has skewed considerably younger over the last few years.

Unlike the Catskills Mountain region, which is far more sprawled out and punctuated only by quaint, post-industrial towns that are a little out of the way from the nature you drove up to see, Great Barrington lies at the foot of Monument Mountain and Mount Everett. Officially named an Appalachian Trail community in 2009, laying out a welcome mat and resources to the millions of hikers that pass through each year, the scenery is a constant reminder of all the possible activities to be enjoyed.

With over 7,200 acres of state forest and hundreds of easily accessible trails only moments from the town’s center, visitors truly choose their own adventure. Take a cinematic cruise down the long flat farm roads, cooing at highland cattle and relaxed quarter horses, or stop to collect a local farmer’s bounty in exchange for a few dollars in the honor system jar. Climb to one of the various summits overlooking the Housatonic River and pause to marvel at the natural ponds and more evergreens than you ever expected to find south of Vermont. Pick up the local Shoppers’ Guide and bounce from antique fair to tag sale to barn sale, collecting rare and valuable items that haven’t yet been priced with a tourist’s inflation. Walk around town while sipping a clean, mindfully-sourced cup of coffee from Ilse, and satisfy a sweet tooth with ice cream from SoCo Creamery or a bag of rare licorice from Coco’s Candy Shop. Ski, snowboard, or snowshoe at Butternut or Catamount in the winter. Take a dip in the Green River in the summer. Play an IRL game of Go Fish with Berkshire Rivers Fly Fishing. Enjoy cuisine that rivals some of New York’s best, and art galleries and live music that you can experience without ever having to move your car. Afterward, if you can bear to part with the town, a drive back to New York is supremely scenic. But why not spend the night at a local inn, which is likely snuggled up to a babbling brook or farmstead? There you’ll understand what makes Great Barrington so great.

Here, your weekend guide to this perfect Berkshire town.

Where to Stay

Since this is the Berkshires—and therefore scenic drive country—hop in your rental and head 30 minutes or so north to check out The Inn at Kenmore Hall (a destination all of its own). There are just five rooms in this 18th-century Georgian-Federal home, which was renovated by fashion designer Frank Muytjens (formerly of J.Crew) and artist and restaurateur Scott Edward Cole. The pair decorated the inn with a note-perfect curation of antiques, mid-century accents, and even furniture from their own former homes, carving out an ambience that masterfully threads the past to the present. The best part? The couple are both innkeepers, lending the accommodation a truly at-home atmosphere.

We waxed poetic about this 19th-century-farmhouse-turned-Airbnb back in 2022—and the sentiment holds true. Owners Michael Bolognino and Nick Spain looked to inspirations including the property’s existing Italianate architecture, as well as Italian modernists and contemporary designers, to curate a rental that is exquisitely distinct. They’ve named the home Filomena, and it’s located in West Stockbridge, about 20 minutes north of Great Barrington. (With its impressive six bedrooms, it’s a great spot for larger groups.)

Over in Egremont, just five minutes from Great Barrington town center, you’ll find a brand new sprawling lakeside retreat. The wooded 30-acre property is dappled with modern cabins to give you that one-with-nature feel from the comfort of your organic cotton fair-trade Sister Moons sheets. Disconnect and dive into the heated pool, take a cold plunge, lounge in the saunas, go boating, play pickleball, get a massage, try out some sound immersion therapy, or just be. The DnD experience means no TVs or phones in the rooms. Instead, allow the sound of lapping waves to take priority over your city thoughts. Move as much or as little as you please and then treat yourself to what feels like a floating meal at Cliffhouse Restaurant, which hangs over the lakefront.

Touch down with some history in Egremont, just a few minutes outside of Great Barrington. The Buttonball Inn dates back to 1786, but the historic charm doesn’t get in the way of modern comforts. The inn has seen many names, owners, and restorations over the last few centuries, but remains a revolving door for musicians passing through to perform at the adjacent concert venue, known by locals as The Barn. Most recently, the inn was brought up to date by Heather Thompson and Doug Grabe, who spiffed up the rooms and added a seasonal dinner service so that you can pregame for the concert with shrimp tacos or a steak. After the last call, you’ll be glad to have a plush bed waiting for you only a few steps away.

If you’re traveling from New York, this rental is conveniently located between Hudson and the Berkshires, just a 25-minute drive from downtown Great Barrington. You’ll be surrounded by nature—the three-bedroom home is right in the middle of a hemlock forest—but this is hardly your creepy cabin in the woods: Bright windows, pops of potted plants, and a celery green color palette set the scene for a cozy stay. In the warmer months, take advantage of the spacious deck and take all your meals outdoors.

Just over the New York border, in Hillsdale, 10 minutes from Great Barrington, Little Cat Lodge is nestled into the foot of Catamount Mountain. In the cold months, this Alpine-inspired lodge, impeccably designed by Loren Daye of LoveIsEnough, serves as the perfect location to defrost by the fire after a day on the slopes. And during the warmer months, a beautiful landscape to lounge by the pool and soak up the vast greenery. Consider whether or not you’re brave enough to try out the CataMonster Zip Tour, the longest zip line in America. Don’t forget to make a reservation for Little Cat restaurant, a particularly excellent stop for a boozy brunch with views.

What to Do

The welcoming gallery is an inclusive environment for art aficionados and casual viewers alike. With an eclectic mix of artists from figurative, abstract, mixed media, ceramics and glass art, you’ll find work from artists like Warner Friedman, Janet Rickus, Michael Zelehoski, and Sonya Sklaroff to rising stars like Stephanie Anderson and Dana Piazza.

Right in the town’s center is a performing art space that hosts a range of esteemed performers. Based on the retro and humble exterior, you might walk past it without realizing how impressive the marquee is, but a few recent headliners include: John Mulaney, Cecily Strong and Jane Lynch. With programming nearly every night—films, lectures, concerts, dance, comedy—you’re likely to catch something worth seeing anytime you’re in town. Don’t forget to check out the Indigo Room next door, for NSFW cabarets—like Pilobolus, lit series, open mic, and more.

This trail not only offers a thrilling and stunning ascent and summit, it allows hikers an opportunity to walk in some famous footsteps. Legend has it that in 1850, authors Nathaniel Hawthorne and Herman Melville had a lengthy conversation on Monument Mountain. The meeting is said to have inspired the genesis of Moby Dick.

Housatonic River Walk

This flat, river-side stretch doesn’t require hiking boots, and can be enjoyed with shopping bags in tow. The easy trail is a great place to stretch your legs after a long drive and get close to nature without fully committing to a wooded endeavor.

Drop in for a hot power vinyasa, a spiritual slow-flow, or take the best group nap of your life in the restore class you didn’t know you needed. This warm, community-forward studio is so welcoming and laid back, you’re free to pop in on a whim after shopping and borrow a mat. Get connected, or disconnected.

Perched above Main Street is Great Barrington’s coveted medspa. Though you might want to hang out in the beautiful waiting room all day, sipping tea and looking through their carefully curated products, your skin will thank you for treating yourself to a custom Environ facial with LED therapy, Gua Sha, and a lymphatic drainage massage.

Wander in to sniff delicious soaps and oils, or derobe for a deep tissue massage. If you’re looking to really reset, book a sensory deprivation experience, a.k.a. a float. Unplug for 60 or 90 minutes in a warm, silent, salted bath—solo or with a partner.

Looking for a more private Berkshire spa experience? Rent the Huht mobile sauna and cold plunge for hourly usage at your rental house, or track down the truck at one of their public events. Owner Andy Huh will set up a completely unique restorative session, featuring a fire pit, lounge chairs, and good-vibes-only playlist.

Where to Shop

If, after a weekend of exploring Great Barrington, you’re ready to pick up and relocate to the Berkshires, you’ll be needing to look the part. For this, we suggest heading to Twigs. This boutique from owner Lisa Nappo is a deftly curated assortment of pieces that echo the relaxed, artistic DNA of the region. Shoppers can expect artful denim by Rachel Comey, floaty dresses from Ulla Johnson, and even a novelty sock or two, courtesy of Hansel From Basel.

The boutique showcases both locally and internationally sourced artisanal alpaca goods. This includes an array of knit and woven items from chunky sweaters to clogs to baby clothes, with lots of gift-worthy accessories and decor pieces in between. Most of the yarn and hand-knit items sold at the store come from the owner’s alpacas, or other regional farms and fiber pools.

Part of the fun of a countryside getaway is the opportunity to interact with farmers. While you may not be taking a sirloin steak or beef shank on your drive back home, many of these stands also offer suitcase-friendly provisions, such as honey, maple syrup, and cheeses galore. For this, add a stop at North Plain Farm to your itinerary, which is a self-serve farm store stocked with their 100% grass-fed beef, pastured eggs and chicken, and more. Plus, gifty picks from local producers like artisanal granola and coffee beans.

If for no other reason, you should drive to Great Barrington to stand in this space (which was expertly converted from a bank) and marvel at all 125+ kinds of cheese. Hands down, this is the most chic cheese store you’ll find on the East Coast, featuring delicacies made possible only by local farms and producers.

Dispensaries are everywhere in the Berkshires, but Farnsworth Fine Cannabis Company is more than a pot shop. At the family run Farnsworth, you’ll find THC products, apparel, and jewelry in a thoughtful and sophisticated environment. The full-service dispensary also offers custom smoking accessories in silver and gold, a rare collection of vintage ashtrays and lighters, and a diamond encrusted jewelry line.

This shop caters to ourdoors-y types with a gardening-adjacent aesthetic (think Plasticana clogs and Barbour jackets). And there's plenty of other stuff in the mix. Countryside-chic separates from Margaret Howell, tie-dye socks to style with Danner hiking boots, fanny packs from Clare V, elegant housewares from Hawkins New York, and activewear from labels like Hikerkind, Halfdays, and On.

Take a piece of Great Barrington home with you from this collaborative gift shop, featuring the town’s most cherished artisans—like Aaron Meshon, Hettle, Ben Krupka Ceramics and Peach Tree Jewelry. From handmade earrings and pottery, to hand-sewn apparel and art—there’s a unique Berkshire token for everyone.

Most secondhand shops in the country require you to roll up your sleeves and hunt for treasures. Friperie has done that for you. Owner Beth Conkey has carefully curated a selection of high-quality, gently used items in great shape. And if you need a little help getting that capsule wardrobe started, Conkey offers styling packages inspired by your moodboards and needs.

Bon Dimanche

You can’t get more locally made than the back of the store, where Bon Dimanche owners silk-screen their Petit Pilou organic cotton kid-centric clothing line. The store has become an art and design-focused studio hybrid that offers a range of apparel, artwork, jewelry, and homewares. If you noticed a dozen pasta or chicken-themed sweatshirts or bucket hats at the farmer’s market, this is the place where you can get your own.

When in the Berkshires, learn to sew, knit, embroider, felt, basket-weave, or crochet. Fiber arts is a trade so popular in this town that local schools start teaching it in kindergarten. If you have any interest in anything related to yarn, head to Hart and get everything you need to begin your granny-approved journey. Don’t know where to start? Pop in for a knit hang and learn from owner and textile artist Jamie Goldenberg herself.

Where to Eat and Drink

This newish spot from Stephen Browning (formerly of Prairie Whale) and his wife Julie bills itself as a “post-farm-to-table restaurant” and takes a fresh approach—no tips, no alcohol, and counter service only. After a pop-up stint at the Great Barrington Farmers Market, amassing quite the fan base, the two finally opened their brick-and-mortar restaurant. Now you can catch them serving up inventive dishes like Japanese sweet potato with labneh, tahini, and chili crisp, perhaps followed by a strawberry rhubarb cobbler with a ricotta biscuit, lemon zest, and ice cream?

From restaurateur Josh Irwin (also of MoonCloud) this new “quick service joint” is next to Great Barrington’s Triplex Cinema and offers a cheap and cheerful (and delicious!) menu of popcorn chicken and soft serve, plus a few other select bites like onion petals, tater tots, and “poppin’ pita”—all served with tasty dipping sauces. Since opening in May 2024, Juju’s has quickly become a beloved destination among locals and visitors, cementing it as an ideal spot for a laid-back meal.

Looking for a dimly lit wine bar that’s both the place to be and zero percent stuffy? Slide on your new clogs and head over to Half Rats for a variety of natural wines and craft beers. Order a bowl of corn nuts and Portuguese tinned fish and unwind in a cozy corner while early aughts nostalgia croons through the speakers. If you’re lucky, you just might end up there on a night local tattoo artist, Sad Tatter, is doing a pop-up, so you can end the night with both a buzz and some fresh ink.

If you were blindfolded and led into this dining establishment, you would be sure you were in the middle of Brooklyn—and that’s because its owner is Mark Firth, one of the founders behind Williamsburg mainstay Marlow and Sons. A low-key outpost for Berkshire diners who crave a Brooklyn-tier menu, Prairie Whale’s rustic bar fills with a crowd that’s after craft beers, artisanal cocktails, and natural wines. Come on Sunday evening to see The Lucky 5, a local jazz and swing band that will help you dance away your Sunday scaries.

While all pizza joints want you to believe that they’ve reinvented the pie, Hilltown is doing something different. Using ancient Neapolitan pizza practices learned in Naples, owner Rafi Bildner uses produce as local as outback to create the most flavorful, sensory-rich slices that will leave a lasting impression. While it’s impossible not to clear your plate, try to leave room for dessert. House-made gelato and zeppoles are worth freeing a button for.

Robbie;s might be the only lunch spot that offers crisp sandwiches, hot slices, live music, and on-demand screenprinting by local illustrators, all under the same roof. Grab a chicken Caesar wrap and unique memorabilia while tapping your foot to bright folk music on a lazy Saturday. It can’t get more Berkshire than this.

Feel like cooking? Stock up at Guido’s Fresh Marketplace, the Erewhon of the Berkshires. While you won’t find a Hailey Bieber smoothie there, you will find zingy seasonal smoothies, various forms of seamoss, beef tallow, bovine colostrum, raw cheeses, local produce and Berkshire-themed gifts. Oh, and a hot bar that might make you decide to not cook after all.

The Best Damn Espresso truck lives up to its name, and then some. The mobile coffee company is run by former Brooklyn javaphiles, Asio and Angela Highsmith, of WTF Coffee Lab. The friendly duo whip their own creams, and masterfully brew morning lifelines like vibrant matcha lattes, raw sugar-pulled Cubans, and the whipped cream-loaded Cafe Con Panna. To caffeinate like a local, text ‘BDE’ to 844.659.1203 to get the exact location of the truck in downtown Great Barrington.