Chester is a town in Windsor County, Vermont, United States. The population was 3,044 at the 2000 census. The town was originally chartered by New Hampshire Governor Benning Wentworth as Flamstead in 1754. The terms of the charter were not met and the town was re-chartered as New Flamstead in 1761. In 1766 a patent was issued by New York that changed the name of the town to Chester, after George Augustus Frederick, the Earl of Chester and the eldest son of King George III.