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Chester is located in Windsor County, 14 miles northwest of Bellows Falls.

Chester was chartered on February 22, 1764. Originally called Flamstead, it was one of the first towns to declare independence from the British. Chester was originally an agricultural and rail hub community. As farms mechanized and trains gave way to trucks, Chester became a residential community with some farming and light manufacturing. It also has developed a tourist industry by maintaining the elegance and charm of a Victorian village and rural countryside.

Chester's population is approximately 2,817.

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