Bucolic and sparsely populated, Litchfield County, in Connecticut’s northwestern corner, is less trodden than the Catskills, Hudson Valley or “out East,” on Long Island, with nary a big box store or traffic jam in sight. While unspoiled nature, agriculture and slower pastimes like hiking, camping and antiquing are draws, its small villages and artistic enclaves are increasingly home to chic shops, modern galleries and, as of this past year, new hotels. You may see a famous face out and about — the fashion designer Diane von Furstenberg, actor Meryl Streep and writer Malcolm Gladwell are among those with retreats in the rolling hills — but locals are conditioned to provide anonymity. This itinerary focuses on some of the more central towns like Litchfield, New Preston and Kent, but, whether dining on fresh trout or immersing yourself in art, there are miles and miles to explore.
Recommendations
Immerse yourself in the outdoors at the 4,000-acre White Memorial Conservation Center, a not-for-profit preserve that straddles Litchfield and Morris. Start at the Nature Museum ($3 to $6; under 6 years old, free), inside the main entry, whose displays feature taxidermized black bears, replica beaver lodges and arrowhead artifacts. Then choose from 40 miles of trails. The Apple Hill Trail, three miles out and back, goes on a steady incline from forest to meadow, culminating in an observation platform at 1,200 feet. The six-mile Mattatuck Trail passes ponds and marshes, under oaks and pines. The most popular is the Little Pond Boardwalk Trail, a 1.2-mile wooden walkway that loops through the wetlands surrounding Little Pond and the Bantam River. You may spot cormorants, herons and belted kingfishers.
The town of Litchfield has welcomed three exciting hotels this past year, with the Abner the most urbane. On the town green, in a restored Romanesque Revival-style courthouse building, the hotel features a rooftop bar called Verdict, a much-needed drinking spot with ample seating that’s open to all. Grab a metal garden chair or rocker and look out across the treetops as you sip your cocktail. Running with the courthouse theme, $16 options include a Plaintiff’s Paloma and Motion to Mai Tai. Since the rooftop is weather-dependent, you can always join the locals at the Village, a classic and lively tavern a few doors down, if it’s too cold or wet.
Most visit West Cornwall, a village of barely 1,500 people about 15 miles northwest of Litchfield, to see the 172-foot-long covered bridge, a 19th-century engineering feat listed on the National Register of Historic Places. Since last year, many are coming for the Pink House, a new restaurant just south of the bridge. Opened by a former fashion stylist, it’s intimate and artsy inside with shearling throws and tapered candles, and an expansive patio with a firepit. The chef Cedric Durand’s bistro-style dishes pull from the local farmers and purveyors. Steelhead trout might be complemented with swiss chard and fava beans ($34) or branzino, with fingerling potatoes and summer beans ($35). Other fan favorites include crunchy fried chicken thighs ($26) and a smash burger on a sesame bun ($22).
At the intersections of Routes 7 and 4 in Cornwall Bridge, a dark-blue building stands like a welcoming station: Cornwall Market. Open since early last year, the hybrid market-cafe has become a lively hub for families and adventurers, featuring a mix of pantry items and local produce, takeaway and made-to-order meals, fresh baked goods and coffee. While you could get a breakfast burrito loaded with scrambled eggs, hashbrowns, bacon and green chiles ($12.50) or a housemade bagel ($3), the pastries, including Boston cream donuts ($4) and cinnamon buns drenched in frosting ($6), are not to be missed.
There are lots of small, niche farms across the county that have been around for generations. Goshen, about 10 miles east of Cornwall Bridge, has a nice sampling that is open to the public, starting with Mike’s Beehives. Its new showroom, which opened this summer, stocks raw honey; products made with beeswax, like lip balm; as well as gear and supplies for beekeepers of all levels. Thorncrest Farm has a wee shop on its property, Milk House Chocolates, whose handcrafted truffles and chocolate uses milk and cream from its dairy cows. Northern Farm & Flowers is among a handful of more traditional farms in town, offering free-range pork, pastured poultry, fresh eggs and other regional goods in its rustic shop. While you’re at it, grab some pumpkins, gourds and corn stalks.
Litchfield has a reputation for good antiquing, but these days its villages teem with more contemporary options. Head west to New Preston where Plain Goods, whose chicly renovated pavilion hall is filled with high-quality basics like tailored utility jackets, boxy linen dresses and Scandinavian-style ceramics. Privet House and D.K. Schulman, in neighboring two-story buildings that back up to a babbling creek, offer more colorful but equally refined objects for the home. Expect items like Belgian towels, vintage coffee table books and framed prints by the Connecticut artist Mary Maguire at the former and French fabric cocktail napkins, leather backgammon sets and colorful stationery goods at the latter. When hunger strikes, the grilled chicken on ciabatta ($16) and spinach, goat cheese and fig salad ($16) are winners at the Smithy Cafe.
Arethusa Farm, a dairy farm in Bantam owned by two former Manolo Blahnik executives, has gained a cult following for its award-winning cheeses and uber fresh ice cream. Arethusa makes the ice cream at its original scoop shop on Bantam Road, next to its high-end Italian restaurant and across the street from its daytime cafe. Join the inevitable line and ponder the classic choices like strawberry, coffee and butter pecan. Treat yourself to a waffle cone ($7.50), enjoying it on one of the teak benches outside.
Kent, about 17 miles west, has been associated with art since 1923, when nine painters and illustrators established the Kent Art Association. The nonprofit remains a community anchor, regularly exhibiting local talent and hosting gatherings. From there, cross to the other side of Route 341 for more modern offerings. Kent Barns, a complex of about a dozen buildings and restored barns, is home to Craven Contemporary, which focuses on photography; Kenise Barnes Fine Art, representing emerging and mid-career artists; and Peggy Mercury, a hybrid Pop Art gallery and beauty boutique. About a quarter mile farther up the road, you’ll hit Morrison Gallery, whose 24-foot-tall ceilings are ideal for sculpture, such as Alice Aycock’s spiraling aluminum piece, “Cyclone,” and oversize abstract canvases by the Connecticut artists Jonathan Perlowsky and Cleve Gray.
Transition to the evening with something more invigorating than a cocktail: a waterfall. Just a few miles up Route 7, Kent Falls State Park is home to one of the region’s many falls and cascades, and this one couldn’t be easier to enjoy. The 250-foot spectacle is visible from the entry (free to in-state cars; $10 for out of state) and parking lot. Meander across a covered pedestrian bridge and snap a photo at the base. Then continue up the stone steps that climb a quarter mile. To get back, you can cross a bridge at the top and take a longer wooded path, or simply double back on the stairs.
While many area restaurants make sourcing local food part of their mission, Ore Hill, back in the Kent Barns complex, elevates the visual experience. Open three nights a week, the restaurant offers a five-course prix-fixe ($110) and seven-course chef’s tasting ($145) using mostly Rock Cobble Farm ingredients, which are both the stars and the finishing details. A roasted-asparagus tart is topped with minuscule violets, for example, while the pink of raw bluefin tuna contrasts beautifully with the green of a nettle-and-mint sauce. A less formal option, in the same post-and-beam house, is sister restaurant Swyft, which serves casual fare like sourdough pizzas (from $18) and a roasted half-chicken ($30), both cooked in its wood-fire oven.
Grab an egg-and-cheese ($6.50) from Wilson’s on Kent’s main drag, then drive about four miles south on Route 7. Fifty-two of the Appalachian Trail’s 2,193 miles wind through Connecticut; one spot to hop on is a nearly five-mile stretch near Bulls Bridge, a single-lane, covered bridge in Kent, built during the Revolutionary War. Just before Bulls Bridge, park on the left side and walk along the road — taking care of vehicles — until you see a green gate and the Ten Mile River Section kiosk on the left. From there, head south along the gushing Housatonic River, following blue trail markers until you see white markers, indicating the Appalachian Trail. Follow them, enjoying river views and relatively flat terrain before ascending to the Ten Mile River summit. Feel the stillness of standing above the valley, and enjoy the downhill hike back.
With the rigor of the hike behind you, celebrate with a locally crafted spirit. Litchfield Distillery offers whiskey tours on the hour until 3 p.m., or you can work through a flight of ales, lagers and I.P.A.s at Kent Falls Brewing Company. There are also several vineyards you could visit. The closest are Hopkins Vineyard, high above Lake Waramaug in Warren, with a wine bar in a 19th-century barn and a sprawling lawn; and Spring Hill Vineyards in New Preston, whose food trucks and trove of outdoor art makes the verdant property even more fun to roam. Check both vineyards for their live music calendars.