Main Street. Photo Kelly Cade

all roads lead to Great Barrington

It’s the Rome of the South County. Home to 7,100 people, Great Barrington is  the southern Berkshires’ business and cultural hub. Visitors come for the fun shopping, superb  restaurants, world-class entertainment, year-round outdoor recreation, and the recreational (and medical) cannabis dispensary that  opened a year and a half ago Theory Wellness.

The dispensary, which was the first such shop to open in the Berkshires (there are now six others), has been a hit (so to speak) with customers who like their weed legal and carefully sourced — and there are millions of them within driving distance who lack legal access to this popular herbal remedy in their home states. Another dispensary, woman-owned Calyx, will soon open on Main Street in Great Barrington, and five more are in the works. Not all residents are happy about the “Best Small Town in America,” as Smithsonian Magazine named it in 2012, becoming “the pot capital of the Northeast.” Others point to the millions of dollars ($2.3 million in 2019) that have flowed into town coffers from a 3% municipal tax and a 3% community impact tax on cannabis sales, all from a single store (do the math and gasp).

Great Barrington was founded in 1766, and its historic districts and quaint residential neighborhoods are within walking distance of open spaces. This is the  birthplace of civil rights leader  W.E.B.Du Bois, and an outdoor interpretive trail at his boyhood homesite is open to visitors.


Saint James Place. Photo Kelly Cade

In non-COVID times, Great Barrington is blessed with a number of lively performing spaces, which have been forced to shut down for the present time. The MahaiweCenter for the Performing Arts, normally the anchor for the cultural life of the town with a full schedule of music, theater, films and other events, is offering online presentations and drive-in movies on the campus of Bard College at Simon’s Rock. The recently renovated church-turned-performance-space  Saint James Place currently has no events on its calendar. The  Guthrie Center  on Division Street is, in normal times, a place to enjoy intimate folk concerts; Arlo himself has a place not far away. We are all eagerly awaiting a chance to once again catch the latest movies at the  Triplex Cinema  downtown, where three screens have grown into four.  Great Barrington is also home to  Bard College at Simon’s Rock, a four-year liberal arts “early college” with its new Bard Academy for ninth and tenth graders.  Berkshire Community College also has a presence in town. The nearby village of Housatonic features renovated mill buildings, dance studios and art galleries.


The outdoor dining area near the Triplex Cinema. Photo Terry Cowgill

Great Barrington was a local pioneer in the farm-to-table movement, and wonderful restaurants are scattered throughout town. All restaurants are serving, following Massachusetts re-opening guidelines, including Baba Louie’s (now at the top of Railroad Street), the Prairie WhaleCafé Adam, the solar-powered Barrington Brewery and Restaurant and its newly opened sister Revival, and Number 10 adjacent to the Mahaiwe. Meet up with friends for coffee or tea and a bite at Rubi’sFuel, and Patisserie Lenox, all on Main Street, or ExtraSpecialTeas on Elm. Or for a drink with light fare at Mooncloud on Railroad Street or Miller’s Pub on Main Street. The Berkshire Food Co-op in its new downtown digs on Bridge Street and Guido’s on Route 7 south of town are both open seven days a week year round for top-notch produce, meat, fish and more. Soco Creamery, on Railroad Street, serves great local ice cream. Something new in Covid times: Railroad Street, right downtown, is closed to traffic on Friday and Saturday evenings and local restaurants have set up tables to serve al fresco. And Barrington Courtyard, through the arcade of the Barrington House building on Main Street, has now set up a friendly outdoor eating plaza where Tangier Café, Miller’s Pub, GB Eats, STEAM and Fiesta Bar and Grill are now serving, with Baba Louie’s for pizza in its own outdoor space just adjacent.


The Bookloft’s new location on State Road. Photo Kelly Cade

As for shopping, stores are open, with requirements that you wear masks and use hand sanitizer — a small inconvenience outweighed by the pleasure of being able to shop again. Cruise Main and Railroad for charming owner-run shops, such as Lennox Jewelers for jewelry and watches, Griffin for clothing and gifts, and Emporium and Antique Soul for vintage jewelry and collectibles. Original art can be found at the Lauren Clark and Vault galleries, as well as Bernay Fine Art. Craft stores One Mercantile, Evergreen, Heyday and the new branch of An American Craftsman display pieces by artisans from the Berkshires and around the world. Books new and old can be found at The Bookloft (in new quarters on State Road) and Yellow House Books, respectively.


Barbara Watkins, proprietor of Evergreen Fine American Crafts, in her store on Main Street. Photo David Scribner

Great Barrington is becoming a mecca for home furnishing shops and design studios. Wingate, opened in 1998 just north of town on Route 7, has grown to become one of the biggest home furnishings stores and design showrooms in the Berkshires. Sett, a tabletop shop, is new on Main Street. Samantha Gale Designs is also on Main, showcasing “the vintage beauty of the farmhouse style.” Just off Main is Hammertown, offering furnishings, “approachable design services,” and more. Destination Design Center on South Hillside Avenue designs and installs kitchens, baths, cabinets, and window treatments, among other things. Find new fixtures for your kitchen and bath at Waterware on Chrissey Road just north of town and at S & A Showplace at 40 Maple Drive just southwest of town.


Main Street’s rainbow crosswalks. Photo Kelly Cade

Interior design studios are also prominent in the downtown landscape. William Caligari Interiors is a full-scope design studio, servicing clients in the Berkshires and beyond. Sue Schwarz operates her design studio Gallery 315 Home from a new office in Saint James Place. British-born fabric guru Jennifer Owen works out of her eponymous design studio on Railroad Street, and Jess Cooney Interior has opened a new studio on State Road. Are you contemplating a makeover? Professionals are standing by.


A view of storm clouds from Monument Mountain. Adobe Stock by jdwfoto

Now get up out of that designer easy chair and get some exercise! Hike up Monument Mountain north of town or try the Housatonic River Walk, a national recreation trail. Work out at the Kilpatrick Athletic Center at Bard College at Simon’s Rock or the Berkshire South Regional Community Center, both facilities are open limited hours and required reservations for work out times. Take dance classes at Berkshire Pulse in the village of Housatonic. But, whatever exertions you may undertake, if you should sprain an ankle, or have a more serious medical emergency during your stay, Great Barrington’s award-winning Fairview Hospital and its efficient ER are there to help.