3 p.m. Take a boardwalk hike
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.
5:30 p.m. Sip in the view
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.
7:30 p.m. Eat locally
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).