Ironically the first man to die in John Brown’s raid on Harper's Ferry was a free black man from Winchester, Heyward Shepherd. Shepherd resided in Winchester with his wife and five children. He worked as a baggage handler at Harper's Ferry on the Baltimore & Ohio Railroad.
On October 17, 1859, as John Brown commenced his raid on the armory at Harper’s Ferry, two of Brown’s raiders were crossing the bridge spanning the Potomac River and encountered Shepherd. The raiders ordered Shepherd to halt, but he did not comply. Brown’s men shot Shepherd, wounding him severely. Shepherd lingered for several hours.
News of Shepherd’s death at the hands of John Brown’s raiders infuriated many of Winchester’s townspeople. The town’s inhabitants organized a special relief fund for the care of Shepherd’s family. Militia troops and citizens of Winchester accompanied Shepherd’s body to its final resting place in the colored cemetery on the outskirts of Winchester.