Known as the Chester House Hotel, it was documented by the Historic American Buildings Survey (HABS) in 1937.

[3] The inn was added to the National Register of Historic Places for its significance in architecture, commerce, and education on July 18, 1974.

It was built from 1810 to 1812 by Zephaniah Drake to accommodate stagecoach travelers.

He sold it to Isaiah Fairclo in 1821, who soon resold it to another Drake.

In 1854, William Rankin, a teacher, purchased the Chester Inn and transformed it into a classical college preparatory school, the Chester Institute.