Born in Baltimore, Maryland, on July 21, 1840, Christian Fleetwood was the son of Charles and Anna Maria Fleetwood, who were both free blacks. Fleetwood received his early education in the home of wealthy sugar merchant John C. Brunes and his wife, the latter treating him like her son. He continued his education in the office of the secretary of the Maryland Colonization Society, went briefly to Liberia and Sierra Leone, and graduated in 1860 from Ashmun Institute (later Lincoln University) in Pennsylvania. He and others briefly published, in Baltimore, the Lyceum Observer, which was said to be the first black newspaper in the upper South. After the Civil War (1861–1865) disrupted trade with Liberia, he enlisted in the Union Army.
Fleetwood enlisted as a sergeant in Company G, Fourth Regiment, United States Colored Volunteer Infantry, on August 11, 1863 He ...