In 1864, Brook Road provided the most direct avenue of approach from the north for Union cavalry raids on Richmond. After defeating Major General J.E.B. Stuart's Confederate cavalry at Yellow Tavern, four miles north of here, on May 11, 1864, Union cavalry under Major General Philip H. Sheridan penetrated Richmond's outer defensive line on the heights above Brook Run, a half mile north. Advancing southward on Brook Road, Sheridan's force encountered Richmond's inner defensive line near present-day Union Theological Seminary. There he met strong resistance from a combined force of regular infantry and local defense troops. On the morning of May 12, Sheridan moved his force to the northeast and retired across the Chickahominy River.
