Pejoratively known as “Darkies Hollow”, this stretch of road was first settled by David and Keisha Shepard. David appears in the Book of Negroes in possession of the certificate of freedom, having at the age of eleven fled his enslaver William Shephard and bound for Port Roseway, Nova Scotia. Through whatever twist of fate, David found himself on Saint John’s Island and unfree, bound to General Edmond Fanning, the lieutenant governor of the colony.
Kishia’s pathway through history is even more difficult to trace. There are a number of Kishia’s in the Book of Negroes. Fanning does not appear in the book accompanying either Kishia or David, but there are plenty of stories of free Blacks indenturing themselves. Sometimes out of desperation, but usually with the understanding that it is temporary.
David found remaining on the right side of the law difficult and appeared in the colonies court records. When he died, Kishia remaried and with her new husband Samuel Martin, established the area of Charlottetown known as “The Bog”.
The Shepards are one of the most prolific Black Loyalist descendant families on the island.
Photo from “The Guardian” see link below.
James, Robert and Lemuel Shepard, descendants of David and Keisha Shepard.