Throughout its history, the court of Orange County has convened in seven different buildings (four courthouses and three residences). The first session of the county court took place on January 21, 1735, at the house of Colonel Henry Willis on Black Walnut Run in the eastern part of the county. From 1735-1739, the county court met at William Robertson’s house and Branham’s Tavern until the location for a courthouse could be built. About 1739, the first formal courthouse was built on the south side of the Rapidan River between Raccoon Ford and Somerville Ford. The site was slightly east of present-day U.S. Highway 522, about half a mile before it crosses the Rapidan River into Culpeper County, near Route 611. This courthouse was surrounded by the clerk’s office, the prison, the pillory, the stocks, as well as a stable.
On November 24, 1749, the court moved to the tavern of Timothy Crosthwaite in the small settlement of Orange (then known as Orange Court House). By May 1752, a new (second) courthouse was built on the two acre tract of Timothy Crosthwait’s lot that he sold to the county the next year. The lot corresponded approximately to the area bounded by present-day Chapman, Main, Short, and Church Streets. The courthouse complex included the “those devices for punishment”, as well as the jail. This courthouse was located approximately where the former Orange police station was located on Chapman Street.
In 1803, a new (third) courthouse was built on the old Crosthwaite’s tavern parcel, then owned by the county. This location is on the site across the tracks from today’s railroad station/visitors’ center. In 1854, the coming of the railroad to Orange caused the courthouse to be moved again shortly afterward.
In July 1859, the current (fourth) courthouse was completed on the corner of Main Street and Madison Road at the site of Bell’s Tavern/Orange Hotel. It was built in the Italianate style with a distinctive square tower which was a drastic departure from the Classical style popular during the pre-Civil War years. By the end of the nineteenth century, a clock had been installed in the tower, and a clerk’s office and jail building had been added to the courthouse lot.