What is now Joint Base Anacostia-Bolling began as the Flying Field at Anacostia, and later called the Anacostia Experimental Flying Field. The field was used by both Army Air Corps and Navy research and testing, and soon housed two separate adjoining bases.

The Army Air Corps field was named Bolling Field, in honor of Colonel Raynal C. Bolling, former Assistant Chief of the Air Service, KIA near Amiens, France, in World War One. Bolling Air Field became Naval Air Station Anacostia after World War Two, and a new Bolling Air Force Base was constructed just south of the old field. The Naval station was named Naval Support Facility Anacostia, after the original name of the site.

Under various names, Bolling has had a central role in much of US aviation history. Bolling was the base of the first airmail route; the site where Charles Lindbergh's Spirit of St. Louis returned to the US; the testing base for Navy seaplanes and Air Force aerial refuelling; the departure field for Lt. Col. (later five-star general) Henry Arnold launched the first test of a long-range bomber flight; was the original home field of the Sacred Cow, the President's official aircraft prior to Air Force One, and was the Headquarters of the Air Force from 1994 to 2005.

Fixed wing air operations ceased at Bolling in 1962, to avoid conflict with Washington National Airport, but the site continued to serve command, media, and intelligence roles, and became the base for the Air Force District of Washington in 1985-1994, and reactivated as the AFDW center in 2005. Bolling was joined with Naval Support Facility Anacostia in 2010. It remains a key link in Air Force and Navy air operations and defense of DC airspace.