In the fall of 1939, seven of Anderson's students pooled their money and bought an airplane. The Baltimore Afro-American's "Capital Spotlight" column captured the moment: "Buck West, Roland Brawner, and John Pinkett have become aviation minded." By May 1940, the group incorporated as the Cloud Club, Inc. Their members read like a directory of D.C.'s Black professional class: Alvin Barnes, Cholly "Buck" West, Link Johnson, John Pinkett Jr., Harvey Strothers, Arthur "Lil' Arthur" Wilmer, Barrington Henry, Harold "Bicycle" Smith, and Roland Brawner. The Cloud Club operated Howard University's Civilian Pilot Training Program, one of only seven such programs at Black institutions. But when they were evicted from Hybla Valley Airport and harassed at Beacon Field, they went searching for a home. They found it: a hundred acres of fallow farmland along the Patuxent River in Croom, Maryland, rented from a white woman named Rebecca Fisher for thirty dollars a month.

Riverside Airfield opened in late 1940 with a single catalog-ordered hangar, a small office building, and four mowed-grass runways. It was modest, but it was theirs. The Cloud Club resumed Howard University's flight training in January 1941, and the field soon buzzed with private students, air shows, and community events. Jazz bandleader Jimmie Lunceford joined the club, helped fund the operation, and had his band members hammer together the earliest buildings. Lunceford earned his private pilot's license at Riverside. One of Anderson's first students, Yancey Williams, had trained here before continuing to Tuskegee. When the Army Air Corps rejected Williams because of his race, he sued the War Department with counsel from Thurgood Marshall. The day after the suit was filed, the War Department announced the creation of the 99th Pursuit Squadron, the first unit of the Tuskegee Airmen. The roots of that historic squadron reached down into the grass runways of this Maryland field.

Pearl Harbor ended civilian flying around Washington, and in February 1942 the Anacostia Naval Air Station commandeered the airfield. The Cloud Club's members scattered to serve: president John Pinkett became a civilian flight instructor at Tuskegee, while airport manager John W. Greene Jr. worked as a senior mechanic at nearby Camp Springs Army Airfield, today's Andrews Air Force Base. Greene, a Georgia native, was the second African American to earn an air transport pilot's license and the first to earn an airplane engine mechanic's license. When the Navy released the field in August 1944, Greene partnered with Dr. Coleridge Gill, a Howard University medical professor and pilot, to reopen it as the Columbia Air Center. The Navy had doubled the runways from four to eight and improved the grading. Greene built it into a thriving operation offering repairs, fuel, hangar space, charter service, and aircraft sales. He also created the first all-Black Civil Air Patrol squadron, Columbia Squadron, whose ranks filled with returning Tuskegee Airmen.

Columbia Air Center's decline was slow and structural. Greene retired in 1954 after his wife's death, and his absence diminished the field's pull. As other airports desegregated, some pilots chose closer facilities. The GI Bill expired in 1956, cutting off funding that many Black students relied on. Then, around 1961, landowner Rebecca Fisher died, and her heirs refused to continue leasing to African Americans. The Capital Flying Club received a termination notice in January 1962. The land became Patuxent River Park. The grass runways returned to meadow, the buildings were demolished, and an aircraft gas pump sat on the ground for decades until the College Park Aviation Museum rescued it in 2000. Captain Fred Pitcher, who learned to fly at Columbia Air Center, was hired by Western Airlines in 1965 as one of the first African American commercial airline pilots. Herbert Jones Jr. went on to train over 150 students, founding "Cloud Club II" in Fort Washington at age 64. The name endured long after the field was gone.