Egremont

From left: Kenver, Old Mill.

“Welcome to Massachusetts” sign, Egremont is, for many travelers, a first glimpse of Berkshire County. It was incorporated in 1775— the same year General Knox passed through on his way to deliver artillery to Boston—but dates to the original treaties signed along the Indian Line in the 1730’s. Thanks to another General (Hugh Smiley), creator of the Old Egremont Society, the buildings and culture have survived intact. By the 1930s, Egremont had become a popular motorcar destination for being “the real New England.” And while today’s automobiles look a lot different, the view from them is much the same.

EAT/DRINK Egremont remains a go-to destination for locals and visitors alike. Long-running establishments include the perennially popular Old Mill (opened in 1978), drawing devoted fans to its circa 1797 grist mill building and familiar menu, while John Andrews Farmhouse Restaurant (1990) gets raves for its upscale farm-fresh cooking in a historic home, with patio dining spilling onto the lawn during the summer. Mom’s Country Café is a bustling diner that’s been dishing out phenomenal breakfast and lunch fare for over 30 years. The adjacent Egremont Market makes a great sandwich to go—and stocks basics for your rental.

In 2016, Egremont made headlines when the close-knit Keene family from New York City restored a dilapidated old barn along Route 23, creating The Barn at the Egremont Village Inn, which rapidly became a renowned venue for dinner, drinks, and live music and comedy performances (plus karaoke). More recently, co-owners Nick Keene and partner Jenny Rubin opened Sara’s Place (named for Keene’s mother, who died in 2021) in the Inn, serving coffee, breakfast, and lunch Wednesdays through Sundays.

Be sure to check out the curated selection of “real wines for the people” and work from local artists at the South Egremont Spirit Shoppe, in an updated building that once housed a manufacturer of axles for horse-drawn carriages. Then climb the stairs from the parking lot to Devine, the first (and only) cannabis shop in Egremont. Over in North Egremont, regulars flock to the Old Egremont Country Store for daily lunch specials from the deli. Expect to see a group of cyclists fueling up en route to Hillsdale or other environs. It also stocks a variety of locally made products, from maple syrup to books by local authors as well as artwork; there’s a little something for everyone here!

SHOP Families have been coming to Kenver for snow sports gear and garb for over 60 years, and in 2014 the handsome, weathered-brick emporium began remaining open in the spring and summer, proffering seasonal outdoor apparel, accessories for the home, and a special room devoted to pets. Plus you can buy or rent a bike here, then pedal off on one of the suggested routes.

If quilting is your “sport” of choice, you’re in luck: Brookside Quilts, located at the junction of Route 23 and Sheffield Rd., sells new and vintage quilts along with all the supplies you need (sewing machines, threads, rotary cutters, and the like) to DIY. Just getting started, or want to brush up your stippling skills? Sign up for one of the workshops. You can even send the kids to a summer quilting camp. You’ll find an eclectic array of candles, decorations, cards, wrapping materials, and gifts of all kinds at The Shop by Only in My Dreams Events, a wedding and event planning service. But it’s worth browsing the Paraphernalia Packs, which feature Berkshire products in a nifty box—those bearing the “Packs with a Purpose” label are connected to a local nonprofit and include a donation to the organization. Drop by on Thursdays for fresh-cut flowers.

The owners of 41 Main Antiques (and Mix on Main, in Sheffield) specialize in 20th-century furnishings and accessories but have an eye for pieces and collectibles from all periods. For now the shop is open by appointment only.

STAY Why not book one of seven comfy rooms—some petfriendly—at The Egremont Village Inn, so you can “wind down your day and party all night in a restored barn while eating perfect pub food, sipping amazing local drinks, and listening to great Berkshire-based and national touring artists performing a few feet away”? (Sold!) The original one-room house was built before the Revolutionary War and over time grew in stature and size until it began operating as a guest house in the 1940s. History sleeps here.

The Inn at Sweet Water Farm may have a Great Barrington mailing address (and GPS locale), but is in the nationally registered historic village of North Egremont, some four miles from the center of GB. “It’s a country charm thing . . . worth the confusion.” The B&B serves homemade breakfast from 8:30 a.m. to the leisurely hour of 11 a.m.—and is open to non-staying guests with advance reservation. While not an active farm, there is a gaggle of hens that lay the eggs that you get to eat.