During the Civil War, both Northern and South soldiers at various times occupied Waterloo. In 1861, CSA General Stonewall Jackson defeated USA General James Shields in an early skirmish; Shields' troops crossed the Waterloo Bridge from Culpeper to Fauquier on his retreat back to Washington, and in March 1862 he would return to help hand CSA General Jackson a rare tactical defeat at the Battle of Kernstown I (about to the north). On August 22, 1862, General J. E. B. Stuart's army started its ride around the army of USA General John Pope Pope in Waterloo. Stuart's force captured Pope's headquarters wagons and destroyed Union supplies and army material, shortly before the second battle of Manassas. By war's end, all but a couple of Waterloo's buildings were destroyed or dismantled. See also "Battle of Rappahannock Station I".