In less time than it would take to read Edith Wharton’s Ethan Frome, you could be enjoying your own charming experience in the Berkshires. While crowds head to the Catskills—an upstate area that’s become a weekend hotspot for Brooklynites—you could go 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). This quaint brick town is as lovely as the fictional Starkfield, but with an artistic vibe and cultural significance that make the two-and-a-half-hour drive from New York well worth it. “Part of the town’s appeal is that it’s not too easy to get to—getting here takes planning, so there’s a sense of successfully preserving what makes this place special,” local travel consultant Rebecca MacGregor tells Vogue.
While the Berkshires have long been a haven for nature lovers and artists, in recent years they’ve attracted a new crowd: young New Yorkers. With new businesses and upgrades to existing cultural spots, Great Barrington has become one of the most popular destinations in the Massachusetts highlands. The town is buzzing with a revival that not only celebrates its long-standing charm but also reflects our farm-to-table, eco-conscious generation. It’s so appealing that on a crisp day, you might find yourself eyeing real estate listings while sipping fresh spiced apple cider from the farmers market. According to the Berkshires’ top real estate agency, the age of city couples flocking to the Great Barrington area has dropped significantly in recent years.
Photo: Getty Images
Unlike the Catskills, which are more spread out and dotted with small, post-industrial towns that feel a bit removed from the nature you came to see, Great Barrington sits at the base of Monument Mountain and Mount Everett. Named an Appalachian Trail community in 2009, it offers a warm welcome and resources to the millions of hikers passing through each year. The scenery is a constant reminder of all the activities waiting to be enjoyed.
With over 7,200 acres of state forest and hundreds of easy-to-reach trails just minutes from the town center, visitors can truly choose their own adventure. Take a scenic drive along long, flat farm roads, admiring highland cattle and relaxed quarter horses, or stop to grab a local farmer’s bounty by dropping a few dollars in an honor system jar. Climb to one of the summits overlooking the Housatonic River and pause to enjoy natural ponds and more evergreens than you’d expect to find south of Vermont. Pick up the local Shoppers’ Guide and hop from antique fairs to tag sales to barn sales, hunting for rare finds that haven’t been marked up for tourists. Stroll through town sipping a clean, thoughtfully sourced coffee from Ilse, and satisfy your sweet tooth with ice cream from SoCo Creamery or a bag of rare licorice from Coco’s Candy Shop. In winter, ski, snowboard, or snowshoe at Butternut or Catamount. In summer, take a dip in the Green River. Play a real-life game of Go Fish with Berkshire Rivers Fly Fishing. Enjoy food that rivals some of New York’s best, and explore art galleries and live music without ever moving your car. Afterward, if you can bear to leave, the drive back to New York is stunningly scenic. But why not stay overnight at a local inn, likely nestled by a babbling brook or farmstead? There, you’ll understand what makes Great Barrington so great.
Here’s your weekend guide to this perfect Berkshire town.
Where to Stay
The Inn at Kenmore Hall
Photo: Courtesy of The Inn at Kenmore Hall
Since this is the Berkshires—prime scenic drive country—hop in your rental and head about 30 minutes north to cCheck out The Inn at Kenmore Hall—it’s a destination in itself. This 18th-century Georgian-Federal home has just five rooms and was renovated by fashion designer Frank Muytjens (formerly of J.Crew) along with artist and restaurateur Scott Edward Cole. They decorated the inn with a perfect mix of antiques, mid-century touches, and even furniture from their own former homes, creating an atmosphere that beautifully connects the past with the present. The best part? The couple are both innkeepers, so the place feels truly like home.
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The Filomena
Courtesy of the Airbnb photographer community
We raved about this 19th-century farmhouse turned Airbnb back in 2022—and it’s still just as great. Owners Michael Bolognino and Nick Spain drew inspiration from the property’s original Italianate architecture, as well as Italian modernists and contemporary designers, to create a rental that’s wonderfully unique. They named it Filomena, and it’s in West Stockbridge, about 20 minutes north of Great Barrington. With six bedrooms, it’s perfect for larger groups.
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The Prospect
Photo: Allie Goldberg
Over in Egremont, just five minutes from downtown Great Barrington, you’ll find a brand-new lakeside retreat spread across 30 wooded acres. Modern cabins let you feel at one with nature while relaxing on organic cotton, fair-trade Sister Moons sheets. Unplug and dive into the heated pool, take a cold plunge, lounge in the saunas, go boating, play pickleball, get a massage, try sound immersion therapy, or just do nothing. The DnD experience means no TVs or phones in the rooms. Instead, let the sound of lapping waves replace your city thoughts. Move as much or as little as you like, then treat yourself to a meal that feels like it’s floating at Cliffhouse Restaurant, which hangs over the lake.
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Buttonball Inn
Photo: Courtesy of Buttonball Inn
Step into history in Egremont, just a few minutes from Great Barrington. The Buttonball Inn dates back to 1786, but its historic charm doesn’t get in the way of modern comforts. Over the centuries, the inn has had many names, owners, and restorations, but it’s still a popular stop for musicians passing through to play at the nearby concert venue, known locally as The Barn. Recently, Heather Thompson and Doug Grabe updated the inn, sprucing up the rooms and adding a seasonal dinner service so you can grab shrimp tacos or a steak before the show. After the last call, you’ll be glad to have a comfy bed just steps away.
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Hemlock House
Courtesy of the Airbnb photography community
If you’re coming 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 sits right in the middle of a hemlock forest—but this is no creepy cabin. Bright windows, pops of potted plants, and a celery green color scheme make for a cozy stay. In warmer months, enjoy the spacious deck and eat all your meals outside.
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Little Cat Lodge
Just over the New York border in Hillsdale, 10 minutes from Great Barrington, Little Cat Lodge sits at the foot of Catamount Mountain. In the cold months, this Alpine-inspired lodge, beautifully designed by Loren Daye of LoveIsEnough, is the perfect place to warm up by the fire after a day on the slopes. In warmer months, it’s a lovely spot to lounge by the pool and soak in the lush greenery. Think about whether you’re brave enough to try the CataMonster Zip Tour, the longest zip line in America. And don’t forget to book a table at Little Cat restaurant—it’s a great spot for a boozy brunch with a view.
What to Do
BernayFine Art
The welcoming gallery is open to everyone, whether you’re a serious art lover or just browsing. With a diverse mix of artists working in figurative, abstract, mixed media, ceramics, and glass art, you’ll find pieces from well-known names like Warner Friedman, Janet Rickus, Michael Zelehoski, and Sonya Sklaroff, as well as rising stars like Stephanie Anderson and Dana Piazza.
Mahaiwe
Right in the center of town, the Mahaiwe Performing Arts Center hosts a wide range of top performers. From the outside, it looks modest and retro, so you might walk right past without realizing how impressive the lineup is. Recent headliners include John Mulaney, Cecily Strong, and Jane Lynch. With shows almost every night—films, lectures, concerts, dance, and comedy—you’re likely to find something worth seeing whenever you’re in town. Don’t forget to check out the Indigo Room next door for adults-only cabarets, like Pilobolus, literary series, open mic nights, and more.
Monument Mountain
This trail offers a thrilling climb with stunning views from the summit, and it also lets hikers follow in some famous footsteps. Legend has it that in 1850, authors Nathaniel Hawthorne and Herman Melville had a long conversation on Monument Mountain, which is said to have inspired the beginning of Moby Dick.
Housatonic River Walk
This flat, riverside path doesn’t require hiking boots and can be enjoyed even while carrying shopping bags. It’s an easy trail, perfect for stretching your legs after a long drive and getting close to nature without diving into a full woodland adventure.
Greenhouse Yoga
Drop in for a hot power vinyasa, a gentle slow-flow, or take the best group nap of your life in a restore class you didn’t know you needed. This warm, community-focused studio is so welcoming and laid-back that you can stop by on a whim after shopping and borrow a mat. Get connected—or disconnected.
L’io Beauty and Wellness
Above Main Street sits Great Barrington’s top medspa. You might want to spend all day in the beautiful waiting room, sipping tea and browsing their carefully chosen products, but your skin will thank you for treating yourself to a custom Environ facial with LED therapy, Gua Sha, and a lymphatic drainage massage.
Mend Sustainable Spa
Wander in to smell delicious soaps and oils, or undress for a deep tissue massage. If you’re looking for a real reset, book a sensory deprivation experience, also known as a float. Unplug for 60 or 90 minutes in a warm, silent, salted bath—alone or with a partner.
Huht
Looking for a more private spa experience in the Berkshires? Rent the Huht mobile sauna and cold plunge for hourly use at your rental house, or find the truck at one of their public events. Owner Andy Huh will set up a completely unique restorative session, complete with a fire pit, lounge chairs, and a playlist full of good vibes.
Where to Shop
Twigs
If, after a weekend exploring Great Barrington, you’re ready to pack up and move to the Berkshires, you’ll need to look the part. For that, head to Twigs. This boutique, owned by Lisa Nappo, is a carefully curated collection of pieces that reflect the relaxed, artistic spirit of the area. Shoppers can find artful denim by Rachel Comey, flowy dresses from Ulla Johnson, and even a novelty sock or two from Hansel From Basel.
Fluff
This boutique features artisanal alpaca goods sourced both locally and internationally. You’ll find a range of knit and woven items, from chunky sweaters to clogs to baby clothes, along with plenty of gift-worthy accessories and decor pieces. Most of the yarn and hand-knit items sold here come from the owner’s alpacas or other regional farms and fiber pools.
North Plain Farm
Part of the fun of a countryside getaway is getting to interact with farmers. While you ma…You might not be bringing home a sirloin steak or beef shank from your drive, but many of these stands also offer travel-friendly items like honey, maple syrup, and plenty of cheeses. For that, add a stop at North Plain Farm to your plans. It’s a self-serve farm store stocked with their 100% grass-fed beef, pastured eggs and chicken, and more. Plus, you’ll find great gift options from local producers, like artisanal granola and coffee beans.
Rubiner’s Cheesemongers
Even if you have no other reason, drive to Great Barrington just to stand in this space—expertly converted from an old bank—and admire over 125 kinds of cheese. Without a doubt, this is the most stylish cheese shop on the East Coast, featuring specialties made possible only by local farms and producers.
Farnsworth
Dispensaries are everywhere in the Berkshires, but Farnsworth Fine Cannabis Company is more than just a pot shop. At this family-run spot, you’ll find THC products, apparel, and jewelry in a thoughtful, sophisticated setting. 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.
Westerlind
This shop caters to outdoor types with a gardening-inspired vibe—think Plasticana clogs and Barbour jackets. And there’s plenty more to explore: countryside-chic separates from Margaret Howell, tie-dye socks to pair with Danner hiking boots, fanny packs from Clare V, elegant housewares from Hawkins New York, and activewear from brands like Hikerkind, Halfdays, and On.
Railroad Street Collective
Take a piece of Great Barrington home from this collaborative gift shop, which features the town’s most beloved artisans—like Aaron Meshon, Hettle, Ben Krupka Ceramics, and Peach Tree Jewelry. From handmade earrings and pottery to hand-sewn clothing and art, there’s a unique Berkshire keepsake for everyone.
Friperie
Most secondhand shops in the country require you to roll up your sleeves and hunt for treasures. Friperie has done that work for you. Owner Beth Conkey has carefully chosen a selection of high-quality, gently used items in great condition. And if you need help starting a capsule wardrobe, Conkey offers styling packages based on your mood boards and needs.
Bon Dimanche
You can’t get much more locally made than the back of this store, where Bon Dimanche owners silk-screen their Petit Pilou organic cotton kids’ clothing line. The shop has become an art- and design-focused studio hybrid, offering a range of apparel, artwork, jewelry, and home goods. If you noticed a dozen pasta- or chicken-themed sweatshirts or bucket hats at the farmer’s market, this is where you can get your own.
Hart
When you’re in the Berkshires, learn to sew, knit, embroider, felt, basket-weave, or crochet. Fiber arts are so popular in this town that local schools start teaching them in kindergarten. If you have any interest in anything yarn-related, head to Hart and get everything you need to start your granny-approved journey. Not sure where to begin? Drop in for a knit hang and learn from owner and textile artist Jamie Goldenberg herself.
Where to Eat and Drink
No Comply Foods
This new spot from Stephen Browning (formerly of Prairie Whale) and his wife Julie calls itself a “post-farm-to-table restaurant” and takes a fresh approach—no tips, no alcohol, and counter service only. After a pop-up at the Great Barrington Farmers Market, where they built a loyal following, the couple finally opened their brick-and-mortar restaurant. Now you can enjoy inventive dishes like Japanese sweet potato with labneh, tahini, and chili crisp, maybe followed by a strawberry rhubarb cobbler with a ricotta biscuit, lemon zest, and ice cream.
Juju’s
From restaurateur Josh Irwin (also of MoonCloud), this new “quick service joint” is next to Great Barrington’s Triplex Cinema and offers affordable…Here’s a polished version of your text:
Juju’s
A fun, cheerful (and delicious!) menu features popcorn chicken and soft serve, plus a few other 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 favorite among locals and visitors, making it the perfect spot for a relaxed meal.
Half Rats
Photo: Courtesy of Half Rats
Looking for a dimly lit wine bar that’s trendy but not at all pretentious? Slip on your new clogs and head to Half Rats for a selection of natural wines and craft beers. Order a bowl of corn nuts and Portuguese tinned fish, then unwind in a cozy corner while early 2000s nostalgia plays through the speakers. If you’re lucky, you might catch a pop-up from local tattoo artist Sad Tatter, so you can end the night with both a buzz and some fresh ink.
Prairie Whale
Photo: Courtesy of Prairie Whale
If you were blindfolded and led into this restaurant, you’d swear you were in Brooklyn—and that’s because owner Mark Firth is one of the founders of Williamsburg staple Marlow and Sons. A low-key spot for Berkshire diners craving a Brooklyn-quality menu, Prairie Whale’s rustic bar draws a crowd 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.
Hilltown
Photo: Courtesy of Hilltown
While every pizza place claims to have reinvented the pie, Hilltown is doing something different. Using ancient Neapolitan pizza techniques learned in Naples, owner Rafi Bildner relies on locally sourced produce to create the most flavorful, sensory-rich slices that leave a lasting impression. Though it’s hard not to finish your plate, save room for dessert. The house-made gelato and zeppoles are worth loosening your belt for.
Robbie’s Community Market
Robbie’s might be the only lunch spot offering crisp sandwiches, hot slices, live music, and on-demand screenprinting by local illustrators—all under one roof. Grab a chicken Caesar wrap and unique memorabilia while tapping your foot to bright folk music on a lazy Saturday. It doesn’t get more Berkshire than this.
Guido’s Fresh Marketplace
Feel like cooking? Stock up at Guido’s Fresh Marketplace, the Erewhon of the Berkshires. While you won’t find a Hailey Bieber smoothie here, you will find zesty seasonal smoothies, various forms of sea moss, beef tallow, bovine colostrum, raw cheeses, local produce, and Berkshire-themed gifts. Oh, and a hot bar that might make you decide not to cook after all.
Best Damn Espresso
The Best Damn Espresso truck lives up to its name—and then some. This mobile coffee company is run by former Brooklyn coffee lovers Asio and Angela Highsmith of WTF Coffee Lab. The friendly duo whip their own creams and expertly 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 find out exactly where the truck is in downtown Great Barrington.
Frequently Asked Questions
Here is a list of FAQs about a travel guide to Great Barrington MA written in a natural helpful tone
General Getting Started
Q Why is Great Barrington called the most charming town in the Berkshires
A It has a perfect mix of a historic walkable downtown a lively arts scene great restaurants and easy access to nature It feels both sophisticated and relaxed
Q What is the best time of year to visit Great Barrington
A Fall for stunning foliage Summer for outdoor concerts hiking and festivals Winter for skiing at nearby Butternut or Catamount
Q Is Great Barrington a good place for a weekend trip from New York City or Boston
A Yes Its about a 25hour drive from NYC and a 2hour drive from Boston Its a classic weekend getaway
Activities Attractions
Q What are the mustdo outdoor activities in Great Barrington
A Hike Monument Mountain for a great view swim at Lake Buel or Guilder Pond float down the Housatonic River or go leafpeeping on the scenic back roads
Q Is it just for hikers and nature lovers or is there stuff to do in town
A Its great for both Downtown has antique shops bookstores art galleries and a fantastic food scene with farmtotable restaurants
Q Are there any famous cultural attractions nearby
A Yes Tanglewood is just 10 minutes away in Lenox Also close are the Norman Rockwell Museum and Jacobs Pillow dance festival
Q Can you go skiing near Great Barrington
A Absolutely Butternut Ski Area is right in town and Catamount Ski Area is just over the border in New York about 15 minutes away
Food Drink
Q Where do locals actually eat in Great Barrington