Solomon Rockwell House

The Moses Camp House is a historic house at 682 Main Street in the Winsted area of Winchester, Connecticut. Probably built about 1840 for one of the region's major merchants, it is a high quality example of Greek Revival architecture. It was listed on the National Register of Historic Places in 1984; it now houses professional offices.

The American Museum of Tort Law is a museum developed by Ralph Nader, located in his hometown of Winsted, Connecticut. The museum focuses on topics of civil justice and "aspects of the legal system that handle wrongful actions that result in injury". The museum opened to the public in September 2015. It is the first law museum in the United States.

The Winchester Soldiers' Monument is a historic war memorial located in a park-like setting at the end of Crown Street in the Winsted area of Winchester, Connecticut. Built in 1889–90, it commemorates the community's participants in the American Civil War. It is one of Connecticut's most architecturally elaborate memorials to that conflict. It was listed on the National Register of Historic Places in 1984.

The West End Commercial District encompasses a single city block of commercial buildings in Winsted, Connecticut. The block, consisting of the north side of Main Street between Union and Elm Streets, is the city's largest grouping of late-19th and early-20th century commercial buildings to survive flooding and redevelopment. It was listed on the National Register of Historic Places in 1990.

The Gilbert School is a privately endowed secondary school that serves as the public high school for the towns of Winchester and Hartland, Connecticut and the public middle school for Winchester. The Gilbert School serves grades 7-12. The school was founded in 1895 as the result of the bequest of William L. Gilbert who, in his will, made provision for the “establishment and maintenance of an institution of learning to be known as The Gilbert School.”

Northwestern Connecticut Community College (NCCC) is a public community college in Winsted, Connecticut. As measured by enrollment it is the smallest or second-smallest of the twelve colleges in the Connecticut Community Colleges system.The school has an open admissions policy. NCCC has about 1,600 full- and part-time students enrolled. A commuter school with no dormitories, the college's primary service area includes twenty towns in Litchfield County. Tunxis Community College in Farmington, Capital Community College in Hartford and Asnuntuck Community College in Enfield are the nearest of the state's other community colleges.Along with credit and non credit certificates, the college grants the Associate in Arts and the Associate in Science degrees.

Winsted is a census-designated place and an incorporated city in Litchfield County, Connecticut, United States. It is part of the town of Winchester. The population of Winsted was 7,712 at the 2010 census, out of 11,242 in the entire town of Winchester. Winsted is part of the Northwest Hills Planning Region.

The Winsted Hosiery Mill, also known as the Whiting Mill, is an industrial complex at 210 Holabird Avenue in the Winsted section of Winchester, Connecticut. Developed in the late 19th and early 20th centuries, it was one of the largest industrial employers in the community for many years, and is relatively unaltered from its period of development. It was listed on the National Register of Historic Places in 1985. It is now subdivided for multiple industrial and commercial tenants.

The Gilbert Clock Factory is a historic factory complex at 13 Wallens Street in Winsted, Connecticut. Developed between 1871 and 1897, its surviving elements are a preservation of the state's history as a center for the manufacture of low-cost clocks. The company was one of the town's largest employers for many years. The surviving buildings were listed on the National Register of Historic Places in 1984; they now house apartments.

Winchester is a town in Litchfield County, Connecticut, United States. The population was 10,224 at the 2020 census. The city of Winsted is located in Winchester. The town is part of the Northwest Hills Planning Region.

Highland Lake is a body of water located within the boundaries of Winchester, Connecticut. It has a surface area of 445 acres (180 ha) and an average depth of 24 feet (7.3 m). The lake is long but not wide, extending approximately three miles (4.8 km) from north to south but only one-half mile (0.80 km) at its widest. It narrows at two points and therefore divides into three distinct sections, known (from north to south) as First Bay, Second Bay, and Third Bay. Highland Lake achieves its maximum depth of 63 feet (19 m) toward the center of Second Bay.The lake is popular for recreational purposes, including boating and fishing. The Connecticut Department of Environmental Protection stocks the lake annually with fish, and considers it a Trophy Trout and Bass Management Lake.Highland Lake is encircled by Wakefield Boulevard, which is a little over seven miles (11 km) long, and its shores are heavily built up with residences (both seasonal and year-round) and dotted with many docks. There have been several historical instances of small rogue wakes hitting the area between first and second bay. Locals attribute that to some underground plate movements between the two areas.

Northwestern Regional High School is a public regional high school located in Winsted, Connecticut, serving the towns of Barkhamsted, Colebrook, New Hartford and Norfolk. Northwestern Regional High School, a part of Regional School District No. 7, is located in the same building as Northwestern Regional Middle School, which serves grades 7 and 8.