Chester is a town in Windsor County, Vermont, United States. The population was 3,154 at the 2010 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. Later, the governing authority of Chester reverted to the 1761 charter by an act of the Vermont legislature, although it left the name "Chester" in place. 2011 was thus the 250th anniversary of the town.
According to the United States Census Bureau, the town has a total area of 55.9 square miles (144.9 km2), of which 55.7 square miles (144.2 km2) is land and 0.27 square miles (0.7 km2), or 0.46%, is water.
A prominent geological feature of the town is the Williams River, a tributary of the Connecticut River, whose three branches come together as a central river and run through Chester. Residents use it extensively for recreation; especially fishing and swimming. The banks, covered bridges, waters and nearby homes suffered major damage during Hurricane Irene in 2011. The flooding was caused by Irene's rains coupled with the basin having poor drainage in the rugged, hilly land with steep slopes.