The Chester Inn was built before the Civil War, in the 1830's, as a private residence by Charles Fowler, a prosperous merchant and banker from Albany, New York. The historic Fowler family cemetery, with its picturesque stone walls, still stands on the property.
The property was acquired some time in the 1880's by Mr. Harry Downs who owned and operated the "Chester House" a large Adirondack hotel across the street.
The present innkeepers, Bruce and Suzanne Robbins, purchased and lovingly restored the house in 1987. The property consists of 13 acres of meadows, barns and carriage house, and a smoke house. The inn faces the main street of Chestertown, a small village surrounded by the beautiful Adirondack mountains.