High Quality Content by WIKIPEDIA articles! Windsor is a town in Windsor County, Vermont, United States. The population was 3,756 at the 2000 census. One of the New Hampshire grants, Windsor was chartered as a town on July 6, 1761 by Colonial Governor Benning Wentworth. It was first settled in August 1764 by Captain Steele Smith and his family from Farmington, Connecticut. By 1820, it was the state's largest town, a thriving center for trade and agriculture.