John Hunt Morgan’s two Kentucky raids in 1862 and 1864 included significant engagements with Union forces at Cynthiana, where his mission was to destroy railroad facilities, disrupt communications, acquire supplies, recruit, and threaten Cincinnati. In the First Battle of Cynthiana on July 17, 1862, Morgan’s cavalry of 875 men, with two cannons, defeated 345 men under Lt. Col. John Landram, including Home Guards and one 12-pounder cannon at the courthouse. Simultaneous Confederate attacks at the covered bridge, the North Main and Episcopal church area, and from New Lair Road on Magee Hill forced Landram’s men to withdraw toward the depot, where most were captured. Confederate losses were 8 killed and 29 wounded; Union losses were 17 killed, 35 wounded, and an estimated 250 captured. The Second Battle of Cynthiana on June 11-12, 1864 unfolded in three stages: at dawn on June 11, Morgan with 1,200 men captured Col. Conrad Garis’s 300 Union soldiers of the 168th Ohio after attacks at the covered bridge and Magee Hill; later that morning at Keller's Bridge, Morgan captured Gen. Edward Hobson with 600 men of the 171st Ohio after they arrived by train too late to reinforce Garis; and at dawn on June 12, Gen. Stephen Burbridge’s 2,400 men, pursuing Morgan from Mt. Sterling, attacked on the Millersburg Pike and overpowered Morgan and Col. D.H. Smith, who was about 1/2 mile south at Magee Hill. Morgan escaped but was driven from the state. Confederate losses were an estimated 70 killed, 100 wounded, and 300 captured; Union losses were 48 killed, 171 wounded, and 980 captured.