Frederick E . Humphreys Frederick Erastus Humphreys ( September 16 , 1883 – January 20 , 1941 ) was one of the original three military pilots trained by the Wright brothers and the first to fly solo . Biography . Frederick was born on September 16 , 1883 in Summit , New Jersey , the only son of Jay Humphreys and Fannie Brush . He attended the Pennsylvania Military College , and won an appointment from New York to the United States Military Academy at West Point , New York . He was made Cadet Captain , he lettered in fencing , and was the top eighth student of seventy - eight in the West Point Class of 1906 . After graduation and commissioning , he was assigned to the Army Corps of Engineers and sent to Fort Riley , Kansas where he worked in bridge construction . 2nd Lt . Humphreys deployed to Cuba during the Pacification Expedition , and a year later , returned to attend the Engineer Officer Basic Course . Humphreys volunteered for assignment to the Aeronautical Division , U . S . Signal Corps and was chosen to replace Benjamin Foulois in pilot training by the Wright brothers . On October 26 , 1909 , after three hours of instruction by Wilbur Wright , he became the first Army aviator to solo in a heavier - than - air craft , and thus the first pilot of the first progenitor of the United States Air Force . The Army ' s sole military airplane crashed on November 5 , 1909 , after which Humphreys returned to the Corps of Engineers . In 1910 , Humphreys resigned his commission to attend to his father ' s business , the Humphreys Homeopathic Medicine Company , founded by his grandfather in 1853 . Thereafter he served as an officer of the company , the last twelve years of his life as its president . National Guard . In June 1915 , Humphreys joined the New York National Guard ' s 22d Engineers Regiment as a First Lieutenant . He was called up with his regiment for Mexican Border service after Pancho Villa ' s raids in 1916 , he served as an aide to Major General John F . O ' Ryan , Commanding General of the New York ( later 27th ) Division . Shortly after his return to New York , the regiment was inducted into federal service for World War I . After initial service with his regiment at the divisional training post at Spartanburg , South Carolina , he was recalled and was transferred to the Air Service in January 1918 . After flight training at Rockwell Field in San Diego , California he was assigned to the first class of the School of Military Aeronautics at the Massachusetts Institute of Technology for advanced technical training . He remained at MIT as head of the school ' s Department of Practical Aircraft Design , and then was made school commander . At about the time of the Armistice , he was assigned to the newly founded Technical Section , Engineering Division , at McCook Field , in Dayton , Ohio , remaining there until he was demobilized in February 1919 . He returned to New York , and was appointed Colonel of the 102nd Army Engineers , a position he had until his retirement due to ill health on July 11 , 1939 . At the time he was the senior Colonel of New York . He was advanced to Brigadier General on the State Retired List . Death . Recuperating from pneumonia in Miami Beach , Florida he had a heart attack and died in 1941 . He was 57 years old , and was buried in Arlington National Cemetery .