Born in Ashtabula County, Ohio, Shepard enlisted as a private in Company I, of the 19th Ohio Infantry, mustering in on April 27, 1861, for a term of three months. During that time he participated in the Battle of Rich Mountain in Randolph County, Virginia (now West Virginia). This first major land battle of the civil war and Union victory propelled General George B. McClellan to command of the Army of the Potomac. According to Shepards 19th OVI muster card he spent three days on extra duty setting telegraph poles, mustering out of this unit August 30, 1861.