Alexander Boyd, Sr., a businessman and founder of Boydton, erected the core of this tavern about 1785. The hostelry thrived, and its presence was a major reason for the selection of Boydton as the Mecklenburg County seat. By the mid-19th century, the tavern had evolved into a rambling frame structure with fancy sawn-work detailing, the work of builder-architect Jacob W. Holt. During the Civil War, Mecklenburg's Confederates mustered here. The tavern closed late in the 19th century, converted first to a boarding school and then to apartments. Since 1988, under the care of the Boyd Tavern Foundation, the building has undergone extensive restoration. It is listed on the Virginia Landmarks Registry and the National Register of Historic Places. In late June 1864, while Confederate Gen. Robert E. Lee and the Army of Northern Virginia defended Petersburg and relied on a steady flow of rail-borne supplies, Union Gen. U.S. Grant ordered a cavalry raid to cut Southern supply lines by destroying track, railroad stations, and bridges. On June 22, 1864, Union Gen. James H. Wilson and August V. Kautz left Petersburg with more than 5,000 cavalry troops to destroy track on the Richmond & Danville R.R. and the South Side R.R.