Theodore Roosevelt in Flight. From the 1958 Theodore Roosevelt Centennial collection at Dickinson State University
While visiting an air meet arranged by the Wright Brothers in St. Louis on October 11, 1910, Theodore Roosevelt was invited by flyer Arch Hoxsey to go up in his bi-plane with him. At first Roosevelt refused, but the lure of adventure must have proved too much for him because he changed his mind. The flight lasted a little over 4 minutes though TR is quoted as wishing it could have lasted an hour. He was the first U.S. President to go up in an airplane, although not President at the time of the flight. Hoxsey, a bit of a daredevil when it came to his flying, would die in a plane crash in December of that year.
You may watch the newsreel of the flight on the Library of Congress’s YouTube channel