Weston is a town in Windsor County, Vermont, United States. Home to the Weston Playhouse Theatre Company, it includes the villages of Weston and the Island. Weston was originally the western part of Andover called West Town. Because Markham and Terrible mountains blocked travel between the town's halves, it was set off and incorporated by the legislature. Set among the Green Mountains, the terrain is very rough and mountainous, but the intervales provided good soil for agriculture and pasturage. A second village grew at the canal cut to divert the West River to power watermills. Called the Island, it developed into a small mill town.