Things to Do in Litchfield County, Connecticut

The rolling green hills of Litchfield County (essentially the upper left corner of Connecticut) are home to some of the great “tweener” towns of New England, not to mention the town of Kent, named by Yankee to the top spot on its “Top 25 Foliage Towns in New England” list some years back. History is treasured here, as evidenced by the meticulously restored homes and the classic village greens. But at the same time, proximity to Manhattan keeps this corner of Connecticut contemporary. Sometimes described as a classier alternative to the Hamptons, the Litchfield Hills are a popular escape for city folk, who in turn have helped raise the bar for restaurants and accommodations in the area — turning what has long been a destination for antiquers into a haven for foodies, too. And all of this, of course, is surrounded by a rural landscape perfect for hiking, canoeing, and other outdoor fun. Heading to the Connecticut hills? Here are our suggestions for some can’t-miss things to do and places to eat and stay in Litchfield County.

Favorite Things to Do in Litchfield County

Get Outdoors!

The options for enjoying the outdoors in the Litchfield County seem almost limitless, but if you have to choose, the segment of the Appalachian Trail that runs through Salisbury and Kent is a great place to start. Look for the trailhead just north of Salisbury on Route 41. A 5½-mile hike north from there will bring you to the impressive view from atop Bear Mountain. Dennis Hill State Park and Haystack Mountain State Park, both in Norfolk, also offer up memorable outlooks via short, semi-easy hikes. (For those opting not to feel the burn, there’s a paved auto road to the top of Dennis Hill.)

Less intense strolls are plentiful throughout the Litchfield Hills. The meandering forest paths of Cathedral Pines Trail in Cornwall or the 35 miles of trails that loop through the 4,000-acre White Memorial Conservation Center in Litchfield are prime examples. Then again, if a day on the water is more your thing, take a guided trip with Housatonic River Outfitters or rent your own gear at Clarke Outdoors, both in Cornwall.

Go Antiquing

The Litchfield Hills area is known as an antique-lover’s paradise, with treasure-filled shops in nearly every town. Prime Finds in Lakeville is worth going out of your way for, and the proceeds support Prime Time House, a nonprofit that assists adults with mental illness. Mill House Antiques in Woodbury is located in a 17th–century grist mill and always has a great selection of furniture and home accessories, while Jeffrey Tillou Antiques in Litchfield boasts three floors of wares of all description.

Shop, Learn & Listen

The Hickory Stick Bookshop in Washington Depot is a notable independent bookstore where bestsellers compete for shelf space with works by the area’s many notable writers. Museums in Litchfield County include the Eric Sloane Museum and Kent Iron Furnace in Kent, the Glebe House Museum and Gertrude Jekyll Garden in Woodbury, and the American Museum of Tort Law in Winsted. For nighttime fun, check out the lineup at Infinity Music Hall and Bistro in Norfolk.

Where to Eat in Litchfield County

Lunch

Located on the village green in Litchfield, the West Street Grill is a lunch and dinner favorite of local celebrities, and for good reason: Quality local ingredients are the stars of the ever-evolving New American menu, which features creative takes on classic dishes and memorable soups. Washington Depot favorite The Pantry is as good as it gets for salads and sandwiches that are perfect for taking on the go (but just as good over wine in the quaint café), and homemade pie for dessert is an extravagance you won’t regret. Comfort food staples such as meatloaf and fish and chips are the order of the day at rustic G.W. Tavern in Washington Depot, which serves a terrific brunch on the weekends. In cooler weather, grab a seat by the fireplace if you can.

Dinner

In 2015, Yankee named Arethusa al Tavolo in Litchfield the best spot for “big-city dining in cow country,” and it’s an honor equally deserved today. Dishes are prepared with prime ingredients, including dairy delights from Arethusa’s famously pampered cows. If you don’t have time for a full meal, you can still grab some cheese for the road at the Arethusa Farm Dairy Store next door, where the ice cream is as fresh — and as delicious — as possible. Another Yankee favorite is Community Table in Washington, which adds honey from its own beehive to the cocktails; other raw materials are sourced from local growers, foragers, and producers. Finally, if you can manage the advance planning, set your sights on RSVP French Kitchen, an aptly named little place in West Cornwall where the seats are few (about 20) and the reservation list is long. But the five-course set menu is worth the effort.

Take-Home Treats

Bring home the bacon, and the ham, and the sausage — even the cheese, trout, and venison, if they’re in stock — from Nodine’s Smokehouse in Goshen; the retail store is tiny but the flavor is big-time. Hardcore Sweet in Watertown (a Cupcake Wars winner in 2013) offers more than 150 flavors of cupcakes, truffles, “ponuts” (a pie-doughnut combo), and whoopie pies, including vegan and gluten-free options.

Where to Stay in Litchfield County

The Mayflower Inn & Spa in Washington offers 25 antiques-decorated rooms and suites, plus several cottages scattered around the property. As a bonus, the formal dining room and more relaxed taproom are among the region’s best dining options.

The White Hart in Salisbury, another Yankee favorite, is a classic 19th-century country inn complete with a wide porch perfectly situated for sunset-watching. The 16-room inn has been restored under the leadership of high-profile investors including writer Malcolm Gladwell and artist Jasper Johns, and the on-site restaurant has been critically acclaimed by everyone from The New York Times and Condé Nast Traveler to Bon Appétit.

Legends on the Farmington in Barkhamsted, meanwhile, offers a classic fishing lodge experience that’s right out of an Orvis catalog: The six B&B rooms are steps from the trout-filled Farmington River’s “best dry-fly hole,” and fishing guides are available. But with a plethora of other outdoor pursuits nearby, guests are lured by the cozy vibe even if they never intend to cast a line.

What are your favorite things to do in Litchfield County?

This post was first published in 2017 and has been updated. 

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