In 1864, Brook Road provided the most direct avenue of approach from the north for Union cavalry raids on Richmond. After defeating Maj. Gen. J.E.B. Stuart's Confederate cavalry at Yellow Tavern, four miles north of here, on 11 May 1864, Union cavalry under Maj. Gen. 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 12 May, Sheridan moved his force to the northeast and retired across the Chickahominy River.