Wyndham Bolling was the son of Archibald and Eliza Armistead Bolling of Richmond. He inherited from his mother two paintings of fox-hunting scenes, said to depict his maternal great-grandfather, Bartholomew Trueheart [1770-1834] on horseback near his estate. The pictures (now in the NGA) were commissioned by Trueheart around 1800 from an unknown itinerant artist. Bolling brought them to the home of his aunt and uncle in Cumberland County, Virginia "West Hill." After Wyndham Bolling's death, the paintings were inherited by his like-named first cousin once removed, Wyndham Bolling Blanton, who sold them in 1948.