Connecticut's Vibrant Community In The Berkshire Mountain Foothills Offers Museums, Shops, And Entertainment

There are places known as destinations, and others you travel through to reach them. However, there's wisdom in stopping along the way to discover what smaller communities have to offer. Winchester, Connecticut, is such a place, with museums, entertainment, and outdoor recreation to entice visitors. Right off the north-south corridor of Route 8 and with Route 44 leading to the state capital of Hartford, Winchester is well located to reach other destinations in the state. Adding to its convenient siting, Winchester is also just a few miles from the Massachusetts border, in the foothills of the Berkshire Mountains, an underrated fall destination. Crossing into Massachusetts, you'll come to the historic hub of Sheffield, and beyond it, riverside Great Barrington and Lee with its historic inns.

The first thing to know about Winchester is that it is conflated with Winsted for good reason: Winsted is a city within the town of Winchester, and they share civic entities like municipal government. With a population now of just over 10,000, Winchester was founded in 1750, whereas Winsted has 6,700 residents. They are in the northwestern part of Connecticut in Litchfield County (named for a town with timeless charm), an area known for rolling hills, farms, and well-preserved historic architecture. Winchester is an hour from Hartford and Bradley International Airport and three hours from both New York City and Boston.

One wouldn't expect the largest collaborative artwork in the world to be in a place as unassuming as Winsted. See this impressive 120-foot-long and five-story-high mural in an artists' community housed in a former mill complex called Whiting Mills. Artists and schoolchildren from around the world have contributed to the scenes of Americans at work — from farmers to construction workers — at the American Mural Project. Another unexpected museum in Winsted is the American Museum of Tort Law. This law protects the public from wrongful injuries like unsafe products. The museum is in Winsted because it was the brainchild of local Ralph Nader, a lawyer and activist. 

Stroll along one of the state's longest Main Streets and you'll find cafes and restaurants, the well-stocked Curious Cat Bookshop, clothing and gift boutiques, and a collection of antique stores. There's also entertainment in this mile-long commercial district. You can go duckpin bowling at Laurel Lanes or work on your golf at Be Under Par. Alternatively, you could spend hours at R&B Sportsworld racing go-karts, driving bumper cars, playing mini-golf and laser tag, and practicing your swing in batting cages. You could also go for dinner and a movie at Gilson Café & Cinema, which also hosts live performances, or stop by Little Barn Brewery for food, beer, and music.

One of Connecticut's largest lakes is Highland Lake in Winchester. Rent a stand-up paddleboard or pontoon –- no boating license required, but renters must be 25 — at the Marina at Highland Lake and enjoy its gorgeous, clear water. Around 3 miles long and 7 miles in circumference, Highland Lake has two public beaches and is stocked with trout. Lake Winchester is a smaller lake in Winsted, and the 82-acre Park Pond is another spot for swimming and fishing. For walking or biking, the 3.4-mile paved Sue Grossman Still River Greenway trail begins at the Winsted DMV and ends in Torrington. 

There are vacation rentals right on Highland Lake starting at $175 per night, with a variety of rooms — some large enough to accommodate big groups. Both properties offer a 25% discount for boat rentals at the Marina. Outside Winsted, two places to stay include The Old Riverton Inn in Riverton (4 miles away) and Legends on the Farmington in Barkhamsted (5 miles away); both start at around $140 per night. A bit farther out (18 miles) is a unique Japanese-themed bed and breakfast called O Gawa Shou in North Granby. As in a traditional ryokan, you'll sleep on a futon on a tatami mat, bathe in an onsen, and eat Japanese food.