The Chester Inn is a historic tavern building in Jonesborough, Washington County; it is one of the oldest extant buildings in Tennessee's oldest town. Dr. William P. Chester built the original Federal-style inn circa 1797-98. The frame building measures eighty-two feet in length and twenty-six feet in width and stands flush to the sidewalk in a manner reminiscent of town lots in Maryland, Virginia, and western Pennsylvania. According to historian Paul Fink, the inn “has no distinctive style of architecture, but its timbers display distinctive marking to show that a sawmill of sorts, either a man-powered saw-pit or a primitive water-powered operation, had by this time come into use.” (1) Located on what was once the major road from the Tennessee settlements to the national capital and the important urban markets of Richmond, Baltimore, and Philadelphia, the inn served thousands of visitors during its existence. Andrew Jackson was honored with a reception at the inn during his presidency. Other famous patrons include James K. Polk, Andrew Johnson, and William G. Brownlow. In about 1880 owners updated the inn with an elaborate Victorian-style projecting porch, adding Italianate-influenced brackets to the building's cornice.
The Chester Inn was listed as part of the Jonesborough Historic District on the National Register of Historic Places in 1969. Four years later, it served as a center for the first National Storytelling Festival, which is held every October by the National Association for the Preservation and Perpetuation of Storytelling. The inn recently has been restored and incorporated into the new headquarters and visitor center of the festival.