The enslaved Bolling family came from an unknown parental lineage but occupied positions which were under the constant eye of the Eppes family. The five members of the family were born during the 1830s and 1840s. The eldest of the Bolling siblings was Sarah (born 1834) followed by Robert (born 1835), George (born 1838), Richard (born 1840), and Patty (born 1845). Sarah was a domestic servant as was her sister Patty who was listed in an 1858 inventory as being a seamstress. Robert was a “valuable carpenter.” George Bolling served in the dining room as the waiting man. Richard’s labors are unknown.

The Civil War split this family apart. Robert was encamped with Dr. Eppes’ cavalry company in the summer of 1861 but ran to the Union lines on August 27, 1861. Sarah and Patty departed the Eppes’ land in 1862. George and Richard did not run off. George remained with the family as they returned home in 1866 and appears infrequently in Richard Eppes’ post-war diaries.