Winchester is a town in Litchfield County, Connecticut, United States.

The town is part of the Northwest Hills Planning Region.

[2] The town is in northeastern Litchfield County and is bordered to the south by the city of Torrington.

Winsted, with a population of 7,321 by far the largest community in Winchester, is in the eastern part of the town.

The town is served by buses of the Northwestern Connecticut Transit District.

7 maintains Northwestern Regional High School, which is partly in Winsted.

[8] Students who live in Winchester can attend Northwestern Regional High School through their Agricultural Education Program.

Experiencing a large decrease in enrollment, the school dropped from serving around 200 students, to just 90.