Haywood Shepherd

Little was recorded about Shepherd (seated on the cart) during his life, and this may be the only image of him.

The Man Haywood Shepherd

Father of five young children. Husband to Sarah, Haywood Shepherd was killed during the raid on Harpers Ferry. 46 year-old Shepherd lived with his family in Winchester Virginia and commuted to Harpers Ferry on the train.

The Monument

For years, the United Daughters of the Confederacy (UDC) searched for a place to memorialize the myth of the "faithful slave." In 1920, the UDC approached the town of Harpers Ferry with the idea for a monument to Haywood (Heyward) Shepherd, a free Black man killed during John Brown’s 1859 raid. The UDC misrepresented the facts of Shepherd’s life even misspelling his name to support the "faithful slave” narrative in Shepherd’s death. After a decade of effort, they succeeded and set the dedication date of October 10, 1931.

The Dedication

Henry McDonald, the white president of the majority black Storer College, enlisted the college’s African American choir, led by Pearl Tatten, to sing at the monument's dedication. During the ceremony, Tatten listened to speakers criticize John Brown, justify the system of slavery, and praise the loyalty and faithfulness of past enslaved people in the South. When the time came for the Storer College Singers to perform, she stood, faced the crowd, and protested: “I am the daughter of a [Union] Connecticut volunteer, who wore the blue, who fought for the freedom of my people, for whom John Brown struck the first blow…We are pushing forward to a larger freedom…in the spirit of the new freedom and rising youth.”

Woodlawn Cemetery-
Washington, DC https://woodlawndc.org/

The monument that Haywood Shepherd's family made for him and his wife Sarah.

Heywood Shepherd's death is listed on the left page line 26.

1902 obituary for Sarah Shepherd, wife of Haywood Shepherd. The obituary notes that Haywood Shepherd was buried in Winchester Virginia and gives a description of him.

1902 Obituary for Sarah Shepherd, wife of Heywood Shepherd.