Winsted is the gateway to the Berkshire Mountains
Located at the edge of the Berkshire Mountains, Winsted was founded at the junction of the Mad and Still Rivers, and its moniker combines the names of the neighboring towns of Winchester and Barkhamsted. In fact, it’s part of the town of Winchester, and the two share a town meeting form of government. “Winchester is a big town with a small city as the downtown. That’s Winsted. It’s got a community college, and students commute from around the area up and down Route 8. There’s also Highland Lake. It has small beaches you can access and a marina where you can launch a boat,” says David Sartirana, a real estate broker with over 20 years of experience and the owner of Northwest CT Realty. Situated 24 miles from Hartford and 97 from New York City, Winsted was one of Connecticut’s earliest industrial centers, with numerous mills and factories. Today, it’s home to 7,200 residents, according to the 2020 Census.
Shopping and dining in town or nearby cities
Downtown began a revitalization through an enhancement plan in the early 2000s, and the plan has worked to bring in new businesses. In 2023, the Friends of Main Street organization began hanging flower baskets from lampposts to beautify the area. The two-mile commercial corridor is home to diverse shops, eateries and entertainment venues housed in turn-of-the-century buildings. Locals can shop for antiques, go duck pin bowling or take a spin on the Go-Kart course. For groceries, the Shops at Ledgebrook contains the Stop & Shop grocery store. The one-stop-shop sells produce, pantry items, pet supplies and alcohol. Winsted eateries offer everything from boba teas to Vietnamese fare to Italian ristorantes. The majority of them are clustered along U.S. Route 44. For even more shopping and dining options, residents travel ten miles to nearby Torrington Commons Shopping Center or Torrington Plaza.
Local lakes, summer camps and a bandstand
At 444 acres, Highland Lake is one of Connecticut’s largest waterways and is a popular spot for fishing, swimming and boating. Filled with maple and oak trees, East End Park can be found in Winsted’s historic downtown. The park’s walking path takes guests past several soldier’s memorials, an 1800s fountain and a bandstand. The parks department also oversees recreational programs like children’s basketball camps, adult tennis lessons and summer camps. The Winsted Senior Center caters to the needs of those aged 55 and over. It operates a daily lunch program, a paratransit service for local medical trips and free exercise classes. Seniors can also play Bingo and card games on certain days of the week.
Memorials, murals and memorabilia
Winsted is home to the American Mural Project. This 120-foot-long artwork is one of the largest collaborative indoor pieces in the world. It’s next to Whiting Mills, a collection of art galleries and retail spaces. The Soldier’s Monument and Memorial Park is one of the city’s most notable features. The castle-like tower is a striking memorial to the more than 300 local soldiers who served in the Civil War. Closed for much of the year, it opens for tours on national holidays like the Fourth of July, Memorial Day and Veterans Day. The Winchester Historical Society occupies an 1813 Colonial Revival mansion and doubles as a museum. It has an impressive collection of Civil War memorabilia and military items, a historic dollhouse and other Victorian artifacts.
Turn-of-the-century housing in Litchfield County
Winsted has more than 3,650 places to live, including detached single-family dwellings, apartments and townhouses. Being close to several colleges means Winsted has a fair number of renters. In fact, 37% of people rent here, while 63% own their homes. Most were built before 1970, with a substantial number being older than the 1940s. From March 2023 to March 2024, 54 homes were sold in Winsted after 49 days on the market. The town has less than one month of available housing supply, selling for an average price of $327,000. “Single-family houses across Connecticut are in short supply, and Winsted inventory is wicked low, making it competitive for buyers. A lot of houses go for more than asking after multiple bids,” says Mr. Sartirana.
Commuting to Connecticut’s capital city
Many workers in Winsted commute to the surrounding towns of Hartford, Springfield and Waterbury for healthcare, manufacturing and retail jobs. Typically, it’s a 28-minute one-way commute, with most workers driving alone over U.S. Route 44 and Connecticut Routes 8, 183 and 263. This is a car-dependent area, although the Northwestern Connecticut Transit District provides a fixed-route bus service and a demand-response service for residents aged 60 and older. Also, park-and-ride lots are located throughout town to help locals reach destinations like Charlotte Hungerford Hospital, 8 miles away or Bradley International Airport, 25 miles away.
Science and engineering programs in highly ranked schools
Winchester Public Schools holds a B from Niche, enrolls over 550 students and is known for its innovative science and engineering programs. It operates two schools for students from prekindergarten through sixth grade. Mary P. Hinsdale School serves prekindergarten through third grade and is unrated by Niche, while the B-rated Pearson School teaches third grade through sixth grade. The A-minus-rated Gilbert School is a private school that serves as the system's public-school option for grades 7 through 12. For higher-education options, Westfield State College, the University of Hartford and Naugatuck Valley Community College have campuses nearby and offer two- or four-year degrees and professional certificates.
Environmental factors
Its location near lakes and two rivers significantly increases the town’s chances of flooding. Historically, the worst flooding happened in the 1950s and destroyed much of Winsted. Since then, the town has built back stronger, partly thanks to the Winsted Local Protection Project. Spearheaded by the Army Corps of Engineers, the project built retaining walls along the riverbanks and widened Main Street. The Corps maintains two dams along the rivers to help control water levels during extreme weather events. The state of Connecticut also oversees the CT Alert program, which will email, text or call registered citizens with updates for a variety of emergencies.
![Daniel Quattro]()
Photography Contributed By
Daniel Quattro
