Windsor is a town in Berkshire County, Massachusetts, United States. It is part of the Metropolitan Statistical Area of Pittsfield, Massachusetts. The population was 831 at the 2020 census. Windsor was first settled in 1767 and was officially incorporated in 1771. The town was named for Windsor, Connecticut, where many of the settlers emigrated from. Originally, th…Windsor is a town in Berkshire County, Massachusetts, United States. It is part of the Metropolitan Statistical Area of Pittsfield, Massachusetts. The population was 831 at the 2020 census. Windsor was first settled in 1767 and was officially incorporated in 1771. The town was named for Windsor, Connecticut, where many of the settlers emigrated from. Originally, the town was named "Gageborough" in honor of British General Thomas Gage, but was changed due to the general's Revolutionary War affiliation.