Early Years and Civil War
Bolling was born on February 28, 1835, in Lunenburg County, the son of John Stith Bolling and Mary Thomas Irby Bolling. He grew up on his father’s farm and was educated at Mount Lebanon Academy before moving to Richmond at age nineteen to become a clerk in a store. The following year he and two brothers founded a wholesale grocery and commission business, which they operated until the summer of 1861. On May 9, 1860, Bolling married Cornelia Scott Forrest, of Lunenburg County. They had three daughters and one son.
On June 7, 1861, Bolling enlisted as a sergeant in the Lunenburg Light Dragoons, which became Company G of the 9th Virginia Cavalry Regiment. He was commissioned a lieutenant on April 28, 1862, and promoted to captain on January 17, 1863. Later that year he was detailed to Brigadier General William Henry Fitzhugh Lee‘s staff as acting assistant adjutant general, and in 1864 he was detached to brigade headquarters. At one time Bolling led the l