On the Bowles side of the family, Abraham Bowles and George Richardson’s daughter Betsy lived on land adjoining The Oaks.

Their son Richard Curd Bowles became a physician, graduating from the University of Maryland in 1861. In September of 1862, after spending a year as a physician in the 44th Virginia Infantry, he was commissioned Assistant Surgeon CSA. Eventually, on 4 August 1864, he was assigned to the Confederate Navy aboard the ironclad ram Tennessee during the battle of Mobile Bay. The Tennessee was the strongest, most powerful ship to date, but surrendered after being battered by four Federal ironclads and fourteen large wooden ships. He wrote that they “marched me and starved me until I became so thin and shadowy, I escaped at night unobserved through the guards.” He walked home to Fluvanna and resumed his medical career as a rural physician.

After his aunt MaryAnn Richardson’s death, Dr. R.C. Bowles bought The Oaks and the 160 acres in Fluvanna. For nearly fifty years Dr. Bowles practiced medicine at The Oaks from the living room, which is still referred to as “the medicine room”. He also placed great emphasis on education, and as a member of the Fluvanna School Board in 1886, he helped found Virginia’s first rural, free, accredited public high school in Palmyra.

Dr. Bowles married three times. His oldest daughter, Mary Eliza, a teacher, never married. She brought the oleanders home from South Carolina about 1900. Perkins Bowles, Dr. Bowles’ oldest son, also became a doctor and practiced in Scottsville.