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Richard F. Holladay was a principal force behind the creation of the Charlottesville-Albemarle Airport, which he managed in its first years. Holladay also served as president of Holladay Aviation Inc, which had the airport as its main center of operations.
Holladay was born in Rapidan and attended Fork Union Military Academy. He had a passion for flight stemming from his high school days and earned certification as a pilot in the mid-1930s. He then, along with his brother Warren, ran a Florida-based aviation company. Holladay married Elizabeth Morrill Holladay, who also was a pilot and flight instructor in the 1930s.
Holladay fought in World War II as supervisor of instrument flight training with the Army Air Corps' Air Transport Command. He earned the rank of major. After many years running Holladay Aviation Inc, he sold the company and worked at Virginia National Bank starting in 1964. He continued to advocate for the airport even after ending his formal roles there.
Holladay was pilot and best man for one of the first-ever airborne wedding ceremonies on July 4, 1938. Holladay recounts, "It was to the best of my knowledge the first wedding ever conducted in the air."