Town of Winchester/Winsted

Nestled in the beautiful Litchfield Hills, Winchester is a charming and historic community with a rich history and a bright future. With its beautiful scenery, excellent schools, and thriving business community, Winchester is a great place to live, work, and play. Whether you're a lifelong resident or a visitor, we hope you'll take the time to explore all that Winchester has to offer. With 32 square miles and a population of 11,500, Winchester claims a wonderful quality of life with beautiful lakes, fishing, boating, fresh water springs and more.

Accessibility & Walkability

Winsted, the four-square-mile downtown area of the Town of Winchester, is highly accessible, sitting at the crossroads of Route 44 (which travels east to Hartford and west to Albany) and Route 8 (which travels north to the Berkshires and south to Waterbury and eventually Connecticut’s “gold coast”). Winsted is also 35 minutes from Bradley International Airport and just 90 minutes from New York City. This makes Winsted an ideal place for businesses, of which there are many in town, and an ideal place for families and individuals to live, whether they work nearby or commute to one of the larger cities nearby. Main Street (which is also Route 44) is charming and easily walkable. It is home to a plethora of restaurants and shops and is a short walk away from one of Connecticut’s largest and most pristine lakes. For more information about Main Street, please visit the Friends of Main Street website at

Arts & Culture

Arts and culture are a feature not just in Winsted, but in the surrounding northwestern corner of Connecticut. Winsted is home to the American Mural Project (AMP), the largest indoor collaborative artwork in the world, standing at 120 feet long and five stories high. Nextdoor to AMP is Whiting Mills, an artisan community home to numerous artisanal shops and studios that are open to the public on a regular basis. In development is the Laural City Playhouse, and right on Main Street is the Gilson Theater, where you can treat yourself to dinner and a movie or a live performance all at the same time. Small art, pottery, and photography studios line Main Street, making it a vibrant and exciting place to be, and the Town is also home to the American Museum of Tort Law, the only museum of law in the world. Winsted is just 15 minutes away in Torrington is the Five Points Art Gallery and the Warner Theatre, 20 minutes eastward is the Farmington Valley, and less than an hour away are both the Bushnell Theater in Hartford and the world-famous Tanglewood performing arts center in western Massachusetts.

Nature & Recreation

Winchester is located in the foothills of the Berkshires, making it a visually spectacular place to live and experience. The town is home to a number of parks, multiple pristine lakes (three of which are publicly accessible with public boat launches), and thousands of acres of publicly-owned land that is available and accessible for hikers, boaters, kayakers, mountain bikers, and the like. In addition to trails, lakes, and rivers, the Town is home to a number of recreation-based businesses and other attractions including R&B Sportsworld, which offers minigolf, bumper cars, batting cages, go-carts, and more; Be Under Par, an indoor golf simulator business; and more. The town is home to a wide variety of recreational and entertainment events year-round: from the Laurel Ball in the spring, to the Firemen’s Carnival in the summer, to the Fall Foliage Festival in autumn, to the Gator Parade in the winter. Businesses and residents looking to join or visit Winchester will not be disappointed by its offerings outside of home and work.

Resources & Services

Winchester is not just home to top-notch Town services; it is also home to Northwestern Community College, the #1 top-ranked community college in Connecticut offering a wide variety of two-year degrees and a bachelor's degree in business. The community college plays host to the Northwestern Entrepreneurial Center, an arm of the college that focuses on helping new entrepreneurs get the connections, experience, and help that they need to succeed. Younger students will attend, beginning in August 2022, the refurbished-as-new Hinsdale School, and the town also has its own middle school (Pearson Middle School) and sends its students to a private endowed academy, the Gilbert School.