Harry, Ely, and Becky Singleton also remained in the Midway area after the war and are listed in the group of freedmen identified in the contract between Isaac Nimmons and Charles Carroll in July of 1865 as working at “the Pinckney Place.” The Singleton name is also connected to Woodlands through William Gilmore Simms, whose mother was named Harriet Ann Augusta Singleton. At the time of her death in 1808, Simms inherited 25 slaves, and there is a possibility that the African American Singletons may be descended from them.
The 1870 Bamberg census lists a Harry Singleton, a 38-year-old black farmhand as head of a household consisting of Rebecca, age 37, and children Hura (sp?), 16, Elizabeth, 14, Christina, 12, Sylvia, 10, Eugenia, 6, and Harry, 2. In 1880, Harry, age 50, is recorded as head of a household that includes his wife Rebecca, 50, and children Hattie, Rebecca, Eugenia, Inae, and a nephew, Robert Olin. Also in that year, a Rebecca Singleton purchased 80 acres of land from Francis Fishburne Carroll just north of and adjacent to Woodlands. (Francis Fishburne Carroll was the son of Charles Carroll, who was a close friend, neighbor, and kinsman of William Gilmore Simms.) Harry Singleton, age 70, appears again in the 1900 Midway census with his wife Emma, 55.