Dorchester County Courthouse and Jail is a historic courthouse building located at Cambridge, the county seat of Dorchester County, Maryland. It is an Italianate influenced, painted brick structure, which was enlarged and extensively remodeled with Georgian Revival decorative detailing in the 1930s. The building entrance is flanked on the north by a three-story tower. It was constructed in 1853, and is the only courthouse designed by Richard Upjohn in Maryland.