Chester is a census-designated place (CDP) in Windsor County, Vermont, United States. The population was 1,005 at the 2010 census. The CDP is a statistical area encompassing three distinct places: the urbanized center of the town of Chester, Vermont; a locale known as Chester Depot, which is separated from the town center by the tracks of the former Rutland Railroad; and the village of North Chester.
For many years, the Steamtown rail collection ran train excursions on these tracks between Chester Depot and Bellows Falls before relocating to Pennsylvania. Today, Vermont Rail System operates freight trains along the line, and the depot is still visited by passengers riding the Green Mountain Flyer, also operated by VTR.
Chester Depot is known for the Stone Village, a street with several stone houses built in similar style. Stone was an uncommon building material in rural Vermont.