"You won’t find a lot of hotels in Great Barrington, and that’s part of how it preserves its retreat-like quality. Of a small collection of inns right within the borders of town, the historic Granville House, built in 1825, is a charming and hospitable option. There are five rooms in the intimate inn, tastefully decorated with no luxuries spared. Around the inn you’ll find rare antiques and retro touches like a jukebox and pool table. Outside you’ll find sprawling views, peace and quiet, all only a three minute drive from downtown Great Barrington."

"This sprawling family-owned and -operated lodge is an institution of the Southern Berkshires. With 31 rooms, ranging from quaint guest room-like accommodations to private standalone cottages, the property is nestled at the foot of Mount Race, and an Appalachian Trail head begins just a few feet from the back porch. A robust brook runs adjacent to the lodge, meaning guests are treated to an endlessly tranquil soundtrack to be enjoyed from the various hammocks that hang around the property. Also on the property is The Stagecoach Tavern, which serves farm-to-table food with live music pairings."

"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."

"If you’re up for a drink, some live music, and fried food, head to just five minutes out of town to The Egremont Barn. Quite literally named, it’s a giant barn set up as a music venue with rows of communal highboys and a fireplace in the back. It’s cozy, the food hits a certain kind of spot, and the musical acts are consistent and impressive. It’s the kind of venue where you’ll hear an unknown folk songstress and deem her destined for stardom. Don’t forget to say hi to the resident farm animals adjacent to the barn."

"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."

"Hike a passage of the Appalachian Trail right from town. This flat, river-side stretch doesn’t require hiking books, 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."

"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."

"This staple furniture and design store is a great place to get inspired about redecorating your living room, while also shopping for goods and gifts like cookbooks, dishware, vegan leather accessories, and more. Head to the basement for a flea market-esque sale of items."

"Grab a bottle of small production, natural wine, or some alcohol- free alternatives. Plan to stop by on a Saturday to taste a little bit of everything and chat with a sommelier about pairings and ways to enjoy some of their niche offerings."

"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."

"Take your time thumbing through books on art, photography, architecture, design, cinema, performance, nature, literature, poetry and more. Observe the curated selection of displayed art and objects of outstanding design, both vintage and contemporary and chat with local artists who frequent this evolving communal space."

"Here you’ll find a sturdy hiking boot that’s surprisingly chic, alpine-themed dishware, vintage fisherman sweaters, and gifts that appeal to both outdoorsy and glamorously warm shoppers alike."

"Browse everything from vintage clothing and furniture to organic perfume and sustainable skateboards. If you want to stumble into a local artist’s pop up or poetry reading and leave the Berkshires with a one-of-a-kind purchase, or you’ll likely find it in this store."

"This cozy cave of a cocktail lounge is a great spot for a decadent specialty drink and a locally sourced charcuterie board that makes it a little bit too easy to keep ordering and hide from the cold. Enjoy a variety of cured meats, curated cheeses, preserved vegetables, toasts, spreads, soups, ahi tuna poke bowls, and desserts, all tucked in an intimate lounge setting."

"This local’s favorite is known for their friendly staff and ever-changing, always delicious seasonal menu. Pop in for a quick, sweet bite to-go, or grab a seat to enjoy a locally sourced lunch and breakfast sandwich selection that shows off the best bounty of the Berkshires."

"Don’t leave the Berkshires without a box of pastries, tarts, mini cakes, and breads from the town’s new open-concept bake lab. The community bakery is focused on natural ingredients and old school methods, and is open on the weekends until they sell out, so get there early to get your fill."

"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."

"One of the last things you might expect to find in this mountain town is an authentic Thai street food noodle shop, but surprises come frequently in Great Barrington. Chef Phornphimon Ezinga brings influences from her traditional home cooking in Thailand to the newly expanded kitchen of Steam, and infuses it with a modern take-out-friendly approach. The pork buns are a squishy delight, the summer rolls capture the season year-round, and the ramen is soul-warming."