In 1777, seven commissioners were appointed to buy up to four acres for a courthouse and prison for Montgomery County, and that year both were located in the former Hungerford Tavern on South Washington Street. After 1779 the jail stood elsewhere, and in 1780 Benjamin Ray supplied stocks, a whipping post, and a pillory. Between 1786 and 1789, Sheriff William Robertson used his new house at 101 South Washington Street as his office and jail, or gaol, and the present house replaced that Robertson house and jail in 1884. In 1801, the county received funds to build a jailhouse at the site of the County Office Building on the east side of Maryland Avenue, then called Perry Street. In 1807, Joseph Scott described Montgomery Court House, erected by the General Assembly under the name Rockville, as having public buildings that were a brick courthouse and jail without either taste or elegance. That jail burned in 1861, and a two-story stone building was erected in 1862. The jailer, Mr. Trail, lived there with his family, and the jail held 20 inmates. A large yard behind the building was the site of the county's last hanging on April 15, 1921. The jail remained in use until a new grey courthouse with jail cells on the top floor was built in 1931, when the old jail was demolished.