Richard Henry Watkins was born around 1825 in Virginia to Henry and Agnes Watkins. His father was a farmer who owned $89,000 of real estate by 1850. The family lived in Prince Edward County, Virginia. He married Mary Dupuy on August 24, 1858, and they had at least five children: Emily, born around 1859; Mildred, born around 1861; Mary, born around 1863; Virginia, born around 1868; and Asa, born around 1873. He worked as a lawyer, and by 1860, he owned $10,000 of real estate and $25,000 of personal property. He enslaved at least 27 people.
He enlisted in the Confederate army on June 24, 1861, and he mustered in as a private in Company K of the 3rd Virginia Cavalry. The regiment took part in the Peninsula campaign, the Seven Days’ Battles, the Second Battle of Manassas, the Battle of Antietam, the Battle of Fredericksburg, the Battle of Chancellorsville, the Battle of Gettysburg, the Overland Campaign, the Shenandoah Valley campaign, and the Appomattox campaign. He was promoted to 2nd lieutenant in April 1862, to 1st lieutenant in October 1862, and he eventually received a promotion to captain. He was wounded in October 1864, and he spent several months recovering. He remained in the army until the end of the war, and he received a parole in May 1865.
He settled in Farmville, Virginia, after the war and resumed his work as a lawyer. By 1870, he owned $10,000 of real estate and $1,000 of personal property. He died in Farmville on July 8, 1905.