Proctorsville is a village located in the town of Cavendish, in Windsor County of the Southern Windsor County region. The village was named for Captian Leonard Proctor, a Revolutionary War veteran who moved his family to the area in the early 1780's from Massachusetts. The family name was also used for the town of Proctor, Vermont.

The Dutton and Proctor families, and the villages of Duttonsville and Proctorsville, feuded for seventy-five years and quit only when young Redfield Proctor (later a United States senator) and Miss Emily Dutton were married.