Miles was the son of Levingston and Sally Rainwater Bobo and one of a group of families who moved to Fayette County from the Spartanburg District of South Carolina. Miles' headstone says only Co H 41st Ala Inf CSA on it; apparently indicating his respect for the Confederacy. His Civil War record indicates he was a Sergeant and a nurse who served until about February 1865 when he deserted and was captured and kept prisoner for the remainder of the war as a deserter from the enemy's side. He married Lucy Ann Allen; they had ten children. After her death in 1888 he married Minerva E Collins.