In June 1864, Confederate Gen. Robert E. Lee sent Gen. Jubal A. Early’s corps from the Richmond battlefields to the Shenandoah Valley to counter Union Gen. David Hunter’s army. After driving Hunter into West Virginia, Early invaded Maryland to attack Washington D.C., draw Union troops from Richmond, and release Confederate prisoners held at Point Lookout. On July 9, Early ordered Gen. Bradley T. Johnson’s cavalry brigade eastward to free the prisoners, and the next day Johnson sent Maj. Harry Gilmer’s regiment to raid the Baltimore area. That same day, during the Union retreat from the Battle of Monocacy, Lt. Col. David Clendenin's 8th Illinois Cavalry withdrew down the Georgetown Pike toward Urbana with Confederate Maj. Frederick Smith's 27th Virginia Cavalry in close pursuit. In Urbana, the Virginians suffered a setback when the Co. F flag bearer was shot in the shoulder and Union cavalrymen seized the flag. Smith drew his saber and led a charge to rout Clendenin and recover the flag, but he was shot and mortally wounded during the clash. The Confederate attack stalled, and Clendenin withdrew without further incident. Smith was buried at the Episcopal church in Urbana alongside Lt. Col. William Tavenner, the former commander of the 17th Virginia Cavalry, who had been killed in an engagement earlier that day; relatives later removed Tavenner's body. On July 10, Union prisoners captured at Monocacy were forced to march with their captors, and when Early's army halted briefly in Urbana, the prisoners were permitted to rest along the roadside. Several occupied Mrs. Windsor's yard near here, where she took their names so she could inform their families. In the confusion, three prisoners crawled behind her house and hid in a cramped bake oven, and a board placed over the opening concealed them until the Confederates continued their march with three fewer prisoners.
