Start from 24 curated places around Kent, CT, then choose the recommendations that fit your guests.
Restaurants & cafés
Ore Hill
The only Connecticut restaurant named to the New York Times 50 Best list in 2023, Ore Hill operates as an intimate tasting-menu room inside the historic Swift-Bull House on Maple Street. Chef Joel Viehland sources nearly everything from Rock Cobble Farm a few miles south in South Kent, and the five-to-seven course prix fixe ($95) rotates with the harvest — fragrant green tomatoes, fresh-pulled beans, tiny raspberries, local burrata. The dining room seats a handful of tables, runs Friday and Saturday only, and feels genuinely exceptional for a village of Kent's size.
Swyft
The more casual sibling to Ore Hill, sharing the same kitchen team and the same farm sourcing philosophy. Swyft is a wood-fired tavern serving charred, blistered pizzas with inventive seasonal toppings, shareable small plates, and a thoughtful drinks list on the lovely garden patio or inside the renovated historic building. It's the go-to weeknight dinner for weekenders who couldn't get an Ore Hill reservation.
Trails & outdoors
Macedonia Brook Loop
The signature hike in Kent — a 6.4-mile challenging loop through Macedonia Brook State Park that climbs to Cobble Mountain (1,380 ft) for sweeping views of the Taconic Range and Catskill Mountains on the New York side. The trail follows the blue-blazed Macedonia Ridge Trail through 2,300 acres of rugged second-growth forest, with a shaded stream walk at the base and steep rocky switchbacks on the way to the summit. The fall foliage seen from Cobble Mountain is among the best viewpoints in Litchfield County.
Kent Falls Red and Yellow Loop Trail
A short but steep 0.8-mile loop in Kent Falls State Park that climbs alongside Connecticut's most spectacular waterfall via a series of staircases and switchbacks, reaching the upper falls viewpoint before looping back down. Despite its brevity, the elevation gain (255 feet) and the drama of the 250-foot cascade make this feel like a proper hike. It is genuinely accessible to families with older children and rewards the effort with views that photographs don't fully capture.
Things to do
Kent Art Association
A two-story gallery at the south end of Main Street that has served as Kent's community art hub since the early 20th century. The association mounts juried shows throughout the year in its two-story exhibition space, mixing established regional artists with emerging voices, and runs an active calendar of openings, artist talks, and special events. Free admission makes it an easy addition to any Main Street walkabout.
Housatonic River Outfitters
The premier fly-fishing outfitter for the Housatonic River, operating out of a well-stocked shop in Cornwall Bridge just north of Kent. The guides here are among the most experienced on the river — they publish a detailed weekly fishing report and know every productive stretch from Bulls Bridge to Cornwall. Half-day and full-day guided wading and drift-boat trips are available for all skill levels, and gourmet lunch is included on full-day outings.
Landmarks & sights
Kent Falls State Park
Home to Connecticut's most dramatic waterfall — a 250-foot cascade that drops in a series of ledges through a wooded gorge on the Housatonic tributaries. The main trail up the falls is short (under a mile) with a staircase to the upper viewpoints, making it accessible to most visitors. The park is at its best in spring snowmelt and after heavy rains when the flow is powerful, and again in October when the surrounding hillsides blaze with foliage.
Bull's Bridge
One of only three covered bridges in Connecticut still open to traffic, Bull's Bridge spans 109 feet across the Housatonic River in a dramatic rocky gorge at the New York state border. Built in 1842 on a site first bridged in 1760 by Jacob and Isaac Bull, it's listed on the National Register of Historic Places. The gorge below is a Class IV whitewater section, and the surrounding area is one of the finest fly-fishing stretches in New England — the Bulls Bridge Trout and Bass Management Area allows catch-and-release fishing year-round.