Dilsey was an enslaved worker who lived and worked at Tuckahoe during the Wight and Allen period. She is thought to have been born sometime between 1845-1849 and was one of the children of Ellen Anderson Smith (father unclear). By 1858 her mother had started a family with Ed Smith. Her siblings were Daniel, Jane, Jordan, Nancy, Harriet, Wallace and Andrew. Like many of her siblings, it is thought that she worked primarily in the fields at Tuckahoe.
Dilsey and her family lived in the North Cabin which still stands along Plantation Street. In 1858 their family of 9 was recorded as having 5 blankets among them.
After the Civil War, it seems that some of the Smith family stayed in the area. The 1870 census lists Ellen and Ed in Goochland County but Dilsey was not living with them at the time. It is unknown if she lived nearby or if she left the area entirely.