By Robin Catalano
Photo: Courtesy of the Connecticut Office of Tourism
The northwest corner of Connecticut is so close to home, it might not come to mind as a getaway. But this region of the state, where the Litchfield Hills merge with the Appalachian Mountains and the Housatonic River winds through varied landscapes, is a fabulous day trip or weekend escape. You’ll find beguiling towns with plenty to explore, from natural beauty to shopping to art. Use these recommendations as your guide, and don’t forget to leave time for serendipitous exploration along the way.
Day 1: Waterfalls, Forests, and Murals
Start a day in Falls Village—appropriately named for its Great Falls, the second-largest waterfall in the state. Experienced hikers will appreciate the Falls Village–to–West Cornwall segment of the Appalachian Trail (entrance on Water Street; look for the parking lot after the hydroelectric plant). The entire 18.2-mile out-and-back path includes some challenging inclines. Or you can enjoy a taste of the AT experience on the shorter 3-mile segment that loops over the Housatonic River. Hikers often stop in at the Mountainside Cafe (mountainside.com/cafe) for a bite.
Planning to get in on the “coolcation” trend? Make your way into Norfolk, the “icebox of Connecticut.” The state’s all-time coldest temperature, a balmy -26°F, was recorded here in 1943, and the town is always cooler than those around it. Belly up to the counter at homey Berkshire Country Store (berkshirecountry.com), which serves mouthwatering stacked-and-grilled delights.
The arts inclined should drive 15 minutes into Winstead, to the American Mural Project (americanmuralproject.org). At 120 feet long and 5 stories high, it’s the world’s largest indoor collaborative mural, depicting workers from all walks of life. Have dinner at Little Red Barn Brewers (lrbbrewers.com). Alongside more than a dozen on-tap craft ales, IPAs, and sours, they serve satisfying pub favorites like burgers, flatbreads, and wings.
As evening descends, grab a seat at Norfolk’s Infinity Music Hall (infinityhall.com), a lime-hued, late-1800s saloon and opera house turned concert venue. The stage comes alive on weekends with musical acts like the legendary Patty Griffin and Grammy nominee Brandy Clark.
Day 2: Wine, Dine, and Design
Pick up breakfast at the newly renovated Cornwall Market (cornwallmarket.com) in Cornwall. The shop stocks pantry and specialty items, plus grab-and-go burritos, sandwiches, and pastries like muffins, croissants, and cardamom buns.
Explore via ebike rental from Covered Bridge Electric Bike (coveredbridgeebike.com; ages 16 and up only). Use their curated maps to route yourself through delightful villages, farmland, and Housatonic River trails. Ask for directions to Thorncrest Farm & Milk House Chocolates (milkhousechocolates.net) in Goshen, a dairy and confectionary that sells 122 varieties of cow-to-bar artisanal sweets.
Or point your wheels over the Cornwall Bridge, which spans 172 feet across the rushing Housatonic River and is one of the few remaining covered bridges in Connecticut, and head into Sharon. In the historic district along Main Street, artist-run Standard Space (standardspace.net) spotlights thought-provoking contemporary art that spans several media. A quarter-mile away, across from the circa-1880 Clock Tower, visit the Sharon Historical Society & Museum (sharonhist.org), which has galleries that interpret early New England life as well as modern takes on arts and crafts.
Sit down for lunch at When Pigs Fly South (whenpigsflysouth.com) on West Main Street. The restaurant honors the barbecue traditions and soul food of the South, with meats cured with proprietary rubs and smoked over a combination of cherry, hickory, and apple woods.
Go shopping in Litchfield, where the main drag, Bantam Road (Route 202), is packed with historic architecture and retail therapy. Among the many standouts, family-run CP Farmhouse (cpfarmhouse.com) stocks an array of Amish-made furniture, farmhouse décor, and gifts. Milton Market (miltonmarketct.com), in sweet Cobble Court, is a home, garden, and apothecary shop with a mix of vintage-inspired products for everyday living. Next door at Little-ish (little-ish.com) find a design-minded collection of toys, clothing, and accessories for babies and kids.
Or kick back and savor a sip at Spring Hill Vineyards (springhillvineyards.com), about 10 miles southwest in New Preston. Sited on an 18th-century farm on the banks of the Shepaug River, the property’s unique microclimate produces distinctive Cabernet Franc and Chardonnay, and their specialty, Marquette, a Pinot Noir varietal. The on-premise Art Silo is a jaw-dropping piece of architecture with a copper-hued spiral metal staircase that leads to an intimate gathering space at the top.
Finish the day deliciously with dinner at Bantam’s Arethusa al tavolo (arethusaaltavolo.com), right next door to Arethusa Farm, where the dairy is always worth a stop for ice cream.
Where to Stay
The new Kent Collection (kentcollection.com) includes three cozy boutique properties in renovated historic buildings, all within a quarter-mile of one another in Kent. The Litchfield Inn (litchfieldinnct.com), on 10 acres in the Berkshire foothills, recently underwent a complete renovation and emerged with a new design—including 12 themed rooms—that fuse colonial roots with modern amenities. For a wellness getaway, book a room at the Mayflower Inn & Spa (aubergeresorts.com/mayflower) in Washington, the town that inspired the setting of popular TV series Gilmore Girls. Book traditional bodywork, skin-care services, and alternative therapies like acupuncture and reiki at the spa.
