Sheffield

From left: Colonel John Ashley House, Berkshire Mountain Distillers.

town in the Berkshires (dating back to 1725), it has the highest concentration of working farms, including one of the largest organic dairy farms (500 cows!) in the country. How it came to also be the antiques capital of the county is a mystery, but who cares! The town, situated just north of the Connecticut border in the Housatonic River Valley, has an astonishing number of quality shops (and nary a single grocery store). It boasts other attractions, too.

EAT/DRINK | Many visitors head straight to The Marketplace Café on Elm Court in the center of town for indoor dining and takeout. The chef-owners created a popular catering business in 1993—the first such farm-to-table enterprise in the Berkshires—and have branched out into four additional “retail” locations, each with its own style (the others are in Pittsfield and Great Barrington). For dinner, longstanding The Bridge Restaurant has changed ownership and is now The Frog, serving pub fare.

Two shops started by young entrepreneurs—Roberto’s Pizza and Bakin’ Bakery—opened right next to each other on Main Street. Sheffield is also home to Big Elm Brewing, the new Massachusetts branch of Sunset Meadows Vineyards, and Berkshire Mountain Distillers, the county’s first legit distillery since prohibition. Stop by any of these visitor-friendly places for a tasting.

The Stagecoach Tavern got its start in an earlier age; go for food and drink and also jazz and events. It’s part of the Race Brook Lodge cluster of buildings in a woodsy setting off Route 41.

SHOP | A variety of antiques shops are conveniently located along Route 7 (aka Antique Alley); traveling south from Great Barrington, keep your eyes peeled on either side for “open” signs at (among others) Painted Porch Antiques, Susan Silver Antiques, Linda Rosen Antiques, Samuel Herrup Antiques, and Mix on Main (with apologies to those not mentioned due to space constraints). Loring Gallery traffics in fine (expensive) art.

If you like your music with strings attached, visit the Magic Fluke for handmade ukuleles, banjos, violins, and more. The shop is open for visitors (call for hours), and orders are always accepted by phone and online. In business since 1946, family-owned Sheffield Pottery sells its own ceramics, as well as all the supplies and materials for home potters. Pot-ters of a different ilk have their own agenda: Sheffield is the site of the state’s first licensed outdoor cannabis growing facility, Nova Farms, “boasting 80,000 square feet of sun-grown, organic cannabis canopy,” according to the company. And The Pass, a retail and cultivation facility owned by Chris Weld (of Berkshire Mountain Distillers fame), is open daily. In Sheffield, the times, they have a-changed!

SEE | Part of the town lies along Route 7, and the charming village of Ashley Falls is just a few miles to the southwest. The Colonel John Ashley House , where the enslaved Mum Bett (later Elizabeth Freeman) lived before suing for and winning her freedom in 1781, is a stop on the Upper

Heritage Trail. The grounds of the Ashley House are open now, but the house itself is not.

The original (historical) iteration was destroyed by fire, but the Upper Sheffield Bridge (aka Old Covered Bridge) was rebuilt in 1999. There’s ample parking so you can stroll across it to a lovely park to a lovely park.

There’s usually something going on at Dewey Memorial Hall (circa 1887), an impressive fieldstone and marble structure on the Sheffield green. The Hall’s woodpaneled interior and soaring beamed ceiling is a popular venue for lectures, art shows, concerts, and contra dances.

STAY | The aforementioned Race Brook Lodge has modernized rooms in barns and cottages, all connected by footpath. A few miles down Route 41 lies Sheffield Lodge, a rustic bed and breakfast.