Designed by Charles L. Carson of Baltimore and built by J.E. Chilecutt and R. H. Stevens, the Dorchester County Jail opened in 1883 and had an attractive view of the Choptank River from its position at the back of the courthouse. There were four tiers of cells on two floors, and the front portion provided a comfortable residence for the sheriff and family.
The Denton Union newspaper called the large, costly building “Dorchester’s Folly” and claimed It would provide criminals with “better board and more comfortable quarters than they ever before had been accustomed to.” The jail’s first occupants were two men arrested for catching oysters without a license.
Despite being listed on the National Register of Historic Places in 1982, the building was demolished in 1994 after a long, contentious battle between preservationists and local politicians.