During the war, Oakland farm was home to participants on each side. George R. Gaither, a prosperous Baltimore merchant, purchased the property, including the house completed in 1811, in 1838. His son, George R. Gaither Jr., served as captain of a local militia unit, the Howard Dragoons, whose members were mostly local landed gentry and slave owners. They trained there in the movements of mounted combat and sometimes staged public parades. After the Baltimore Riot of April 19, 1861, the Howard Dragoons helped keep the peace there, but Gaither and most of his men chose to join the Confederate army and rode to Leesburg, Virginia, in May. The unit was periodically reassigned as Company K, 1st Virginia Cavalry, Company M, 1st Maryland Cavalry, and Company K, 2nd Maryland Cavalry. Gaither was captured at Manassas Junction on August 27, 1862, then exchanged, and he resigned in 1863 while suffering from hemorrhoids, a common affliction among cavalrymen. On July 15, 1865, he signed the oath of allegiance. Brothers Moses, William, and Joseph Shipley were enslaved men who labored there and on neighboring farms. In 1863, they enlisted in the 9th U.S. Colored Troops, a regiment recruited in Maryland. William Shipley was killed at Deep Bottom near Richmond, Virginia, in August 1864. Moses Shipley survived the war. Joseph Shipley also survived, but suffered from what is today called post-traumatic stress disorder; increasingly confused and disoriented, he sometimes marched and shouted about the war in public, and family members committed him to successive mental institutions from the late 1860s until his death in 1928.