During the American Civil War, the Hampshire Guards and Frontier Riflemen joined the Confederate Army. Although there were no major battles in Hampshire County, Romney changed hands at least fifty-six times during the war. It was often a case of one army evacuating the area allowing the opposing army to move into the town. This places Romney second behind Winchester as the town that changed hands the most during the American Civil War. On June 11, 1861, it changed hands twice in the same day. Some local Hampshire County historians speculate that Romney actually changed hands more than Winchester, but there are no surviving records to support the claim.