Heyward Shepherd

Biography by Jonathan A. Noyalas

Ironically the first man to die in John Brown’s raid on Harpers Ferry was a free black man from Winchester, Heyward Shepherd.  Shepherd resided in Winchester with his wife and eight children.  He worked as a baggage handler at Harpers Ferry on the Baltimore & Ohio Railroad. 

On October 17, 1859, as John Brown commenced his raid on the armory at Harpers 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.

A monument to Shepherd’s memory was erected in Harpers Ferry in 1931.  Financial contributions for the memorial came from many groups including the United Daughters of the Confederacy and the Sons of Confederate Veterans.