Richard Davidson Ashley was born in Chowan County, NC in May 1850. Therefore he was between 12 and 14 years old when his father came home from his short time in the Confederate Army in April 1862. Richard was too young to serve but evidently went north looking to enlist. On October 3, 1862 he enlisted in Company F of the 2nd Regiment of the Virginia Infantry at Bunker Hill, Berkeley County, Virginia.

The 2nd Virginia Infantry was formed in Charles Town in Berkeley County, VA in 1861 and was instrumental in seizing the arms making equipment at Harpers Ferry for the Confederacy in 1861. They went on to fight at First Manassas in July 1861 and the campaign for Northern Virginia through March-July 1862. They also fought at Second Manassas in August 1862. It was in the interval between Second Manassas and Fredericksburg that Richard enlisted in this battle-hardened unit at Bunker Hill in Berkeley County. However, on November 25th Richard chose to desert at New Market, possibly because the troops knew he was too young. He most probably bounced around trying to find a place to belong but eventually fell into the hands of the Federals who granted him leniency. On August 9th, 1863 Richard signed an oath of allegiance disavowing the Confederacy. This was not long after the Battle of Gettysburg at which the 2nd Virginia Infantry suffered 8 percent casualties.

After the war he worked on the farm of a former Confederate soldier near Suffolk before he married Texanna Umphlett. He lived the rest of his life in the Suffolk area about 30 miles from Chowan County. He is listed on the memorial to Confederate Soldiers in the Courthouse at Suffolk, VA. Although he never claimed on census forms to have been born earlier than 1848, his gravestone shows a birth year of 1844. This is probably in recognition that the minimum age to enlist in the CSA was 18.