During John H. Morgan’s 1st Kentucky Raid on July 17, 1862, 875 Confederate troops entered Cynthiana by the Georgetown Pike as 350 U.S. troops and Home Guard defended the town from houses. Morgan attacked across the Licking River and outflanked the defenders, who surrendered after two hours, with about 40 Confederates and 90 U.S. soldiers killed and wounded; Morgan was surprised by the unexpectedly strong defense. In mid-1864, Morgan raided Kentucky from Virginia, but discipline had broken down and some Confederates robbed a Mount Sterling bank before reaching Cynthiana on June 11. There they defeated Union defenders and burned part of the town to force defenders from houses, but Morgan’s men were routed the next day north of town, and the defeated Confederates fled back to Virginia.