Great Barrington: The coolest small town in the Berkshires

Back in the early days of The WeekEnder, we explored the northern Berkshires, with its buzzing art scene. This weekend, we’re headed to the southern part of the region in western Massachusetts — Great Barrington, to be exact, a place so chic it has been featured in Vogue. GB, as the locals call it, has a history of making headlines: Back in 1850, Herman Melville and Nathaniel Hawthorne picnicked together atop Monument Mountain, which towers over the tiny town, and discussed the future of American literature.

In recent years, a new generation of creative types has discovered this little enclave that blends urban sophistication and natural beauty. “Great Barrington is one of the few places on earth where you can wake up in the morning in a major metropolis, hop in the car and arrive at your destination in time for a brunch of farm-fresh eggs and locally roasted coffee with cream from cows that you passed on the way into town,” says Robin Helfand, founder of Robins Candy, a local sweets shop that is filled with handcrafted chocolates and vintage treats. “Then you can hike Monument Mountain, which has 360-degree views of two different mountain ranges. You can have lunch along the Housatonic, which flows right through town, visit several art galleries, and browse in all the independent shops.”

After raising her three children in Manhattan, Germany, and Australia, Robin says she was lured by the hidden gems, the outdoor activities, and GB’s welcoming sense of community. “I’m really fascinated by places where you can do a lot in a little bit of time,” she says. “I’ve had the privilege of living in several different countries, so I can say that it’s truly a special place, whether you’re living here or just coming to visit for the weekend.”

Mindy Miraglia lived in the Berkshires briefly as a child, then moved back in 2011 for what she thought was going to be a four-month volunteer gig working at Kripalu, a health retreat in the area. She has been in the Berkshires ever since. After taking an inspiring journey along Spain’s Camino de Santiago, she decided to replicate the concept here with Berkshire Camino, which takes guests on walking tours. Like the Camino de Santiago, Mindy says the Berkshires has a spiritual edge to it. “We’re very much in touch with the Native American heritage thanks to the local Stockbridge–Munsee Community, which descended from the Mohicans,” says Mindy. “When you're walking along a river bank, you feel the energy of the people who walked here thousands of years ago.” One of the other highlights of traveling through the Berkshires is — of course — GB. “It’s a place where you can walk the road less traveled and discover something around every corner,” says Mindy.

So join us as we take the road less traveled which, to borrow the words of Robert Frost, will make all the difference.

-Laura Begley Bloom, New York's Senior WeekEnder Writer

The hotel selection in GB is small but packs a powerful style punch.

The taste level runs high at this five-room 1825 inn that is the passion project of a couple who worked with Danny Meyer in New York City and long dreamed of moving to the Berkshires to open an B&B. “It is so cozy and so well thought out,” says Mindy Miraglia. “The owners Terry and Terri are longtime hospitality people, so they really know what they’re doing.”

Sarah Eustis, CEO of Main Street Hospitality (which has hotels all over the Berkshires), lives in GB and couldn’t resist this retro motel when it came on the market. “It has been a long-standing property since the 60’s. We saw an opportunity to give it a modern personality,” she says. These days, you’ll find a roaring pellet stove in the lounge and a fire pit on the front lawn. Another perk: “We love pets and welcome them in all rooms — we have become the destination in the area for pet travel.”

Local gallerist Carrie Chen owns this tiny bed and breakfast, conveniently located right above cool boutiques in the heart of downtown. “She has a very large breakfast room,” says Robin Helfand. “She’s quite passionate about every detail, from the beds to the linens to the quality of the coffee. And the dedicated staff will make you feel very pampered.”

From chef-run restaurants to hole-in-the-wall global dining, you’ll find it all in Great Barrington.

Marjoram + Roux - Chef Daire Rooney has a cult following in the area (fun fact: she used to be Meryl Streep’s private chef). Her latest project is an airy spot with an ever-changing menu of seductive dishes like a grilled mushroom tartine topped with fresh goat cheese.

Pixie Boulangerie - This is the bakery of your dreams — think handmade sourdough bread, chocolate ganache babkas — all made using old-school techniques.

Fuel - “Fuel is a real anchor in town, a gathering spot with great coffee,” says Robin Helfand.

ExtraSpecialTeas - This tea house employs adults with special needs, giving them a safe and nurturing environment to reach their potential, and serves tea and treats that are just as amazing as the mission.

Patisserie Lenox - A French pastry shop and cafe with the most divine organic lunches and sweet treats.

Taft Farms - This 55-year-old family-run local institution sells farm-fresh sandwiches to go from its onsite deli.

Rubiner’s Cheesemongers & Grocers - Owner Matthew Rubiner is somewhat of a spiritual guide when it comes to cheese, offering up profound insight and more than 125 different kinds of fromage.

Guido's - GB has a healthy share of high-end grocers and this is one of the best, with individual stands selling everything from prepared food to flowers.

Great Barrington Winter Farmers Market - One of the few year-round farmers markets in the region moves inside for winter, showcasing the rich resources of the Berkshires.

Barrington Brewery - Family-friendly pub grub. “Great beer flights,” says Robin. “In the winter, that’s where you can find the family of six, all wearing their ski boots.”

Baba Louie’s - Thanks to Covid, it’s just takeout for now, but the woodfired sourdough pizza is worth bringing back to your hotel room or eating in the gazebo behind town.

Taqueria Azteca - There are several Mexican spots competing for local love (including Agaves Mexican Grill and Xicohtencatl) but this is Robin’s favorite. “It’s a hole in the wall that’s nothing to look at: The same woman has been cooking for as long as I can remember, and it’s amazing.”

Bizen - First-class Japanese in the mountains of Massachusetts, from sushi to kaiseki.

Steam Noodle Cafe - Keep an eye out for this Asian street food hot spot that’s moving to a new location; it should be opening any day now.

Prairie Whale - Mark Firth, cofounder of Marlow & Sons in Brooklyn, ditched the city, bought a farm, and opened this rustic-chic restaurant in a former antiques store. “It’s all the rage and everyone wants to go,” says Mindy. “It’s got a great Berkshires vibe.”

Cafe Adam - Born-and-bred Berkshires chef Adam Zieminski cut his teeth working alongside chefs like Daniel Boulud and Thomas Keller and is now the force behind this farm-to-table restaurant.

Mooncloud - “If I want to have a fun cocktail, this is where I go,” says Mindy. “The bartender puts on a show, and there’s also a menu with definite noshing opportunities.”

SoCo Creamery - Micro-batch handcrafted ice cream made with ingredients sourced from local family farms.

Here’s where the locals go to breathe in the fresh air of the Berkshires and have a winter adventure.

Berkshire Camino - Guided walks that weave from town to town along a web of wilderness trails. The experience is based on the pilgrimage mindset that owner Mindy Miraglia discovered by walking Spain’s Camino de Santiago.

Monument Mountain - This epic mountain is on everyone’s hit list, but Mindy has a secret tip: “What a lot of people don't know is that you can walk up the backside of Monument Mountain from Route 180 to a scenic overlook called Flag Rock, which overlooks the village.” A tip: You’ll need microspikes for the winter hike, but the killer views are worth the effort.

Lake Mansfield Loop - “A local insider place that’s magical all year round,” says Mindy. “It’s frozen over right now, and if you’ve got shoes with traction, you can walk on the lake or go ice skating.”

Housatonic River Walk - “A block or two off the Main Street is this short pretty trail that runs right along the river,” says Mindy. “It’s actually nicer in the winter.”

Butternut - Sure, there’s Catamount Ski Area 15 minutes away in Egremont, but Great Barrington has its own family-friendly mountain, Butternut, with 10 lifts, several terrain parks and awesome snow tubing.

With deep history and a rich cultural scene, GB keeps travelers entertained.

W.E.B. DuBois National Historic Site - GB is the birthplace of the preeminent Black leader and civil rights champion who helped create the National Association for the Advancement of Colored People (NAACP). A self-guided trail takes you to his original family homestead.

Mahaiwe Performing Arts Center - This historic theater from 1905 has a serious cultural lineup, with dance, music, theater, opera, and more.

Saint James Place - A restored church that hosts everything from performance art to baroque music to chamber music.

Carrie Chen Gallery - Style maven Carrie Chen (see The Barrington hotel, above) showcases talented local and global artists.

Bernay Fine Arts - Originally from Chicago, this gallery brought its eclectic POV to GB in 2019.

“Covid has actually helped GB to evolve more quickly, with talented and creative people moving in full time,” says Sarah Eustis of Main Street Hospitality. “Great new retail, creative concepts, and engaged people.” Here’s a small sampling of the best shopping in town.

Familiar Trees - Part bookstore, part art gallery, Familiar Trees is the brainchild of two former New Yorkers who used to work in costume and set design (clearly).

Fluff Alpaca - Like the Granville House, this is another passion project for a couple who always wanted to move to the Berkshires. They purchased an old dairy farm, started raising alpacas, and now make gorgeous clothing. “Warm and fluffy stuff — perfect for winter,” says Robin Helfand.

Karen Allen Fiber Arts - You might recognize the name: This shop is from the actress who was in the Indiana Jones movies.

One Mercantile + Sett - A pair of hipster general stores with candles, aromatherapy, housewares and more.

Farnsworth Fine Cannabis - A luxury dispensary selling all your weed needs, plus gorgeous accessories and jewelry.

Calyx - A more approachable dispensary right near Robin’s Candy. “We give you a treat if you show us that you’ve been shopping there,” says Robin.