The town of Winchester was settled in 1732 and incorporated in 1771. The city of Winsted is located within Winchester’s borders. During the 20th century, it was famous for clock manufacturing.
Being located in the northwest part of the state, Winchester is known as the Gateway to the Berkshire Mountains. Today, the town is a popular tourist destination for its notable 19th-century architecture and one of the biggest lakes in the state, Highland Lake.