Ovington trained at Louis Bleriot’s flight school in Pau, France, learning to fly at the controls of a Bleriot monoplane like this one. He received his pilot’s license on January 20, 1911 at age 32. Before returning to the United States, Ovington purchased and outfitted his own Bleriot – a racing monoplane with a powerful engine that he dubbed Dragonfly.

In France, Ovington experienced the dangers of flying firsthand, witnessing several accidents and injuries to fellow students. He made a habit of taking safety precautions, and purchased for himself this French Roold flying helmet made of lightweight cork. The distinctive headgear, typical among early European pilots, would set Ovington apart from other exhibition flyers in the United States.

Ovington made his exhibition debut in May 1911, at a Bridgeport, Connecticut, aviation meet. The novice pilot made an early name for himself, beating prior attempts to take off from an almost impossibly short runway. This feat marked the beginning of a grueling American exhibition tour for Earle Ovington.

As aviation meets gained popularity throughout 1911, promoters sought to exceed public expectations. Event organizers staged riskier contests, such as competitive racing, and pilots attempted increasingly dangerous stunts. While up to these challenges, Ovington remained cautious. He always strapped into a safety belt hooked to the pilot’s seat, to secure him in the event of an accident.

Cross-country races, introduced in the United States in 1911, challenged pilots’ navigation skills. Earle Ovington learned to steer not by landmarks, which were difficult to identify from the air at high speeds, but with a compass and map. Placed directly in front of the pilot’s seat, this roller case allowed Ovington to move the map as he flew.

To the right of his map and compass, Ovington could reference this inclinometer, or level indicator. The device showed Ovington whether he was climbing, descending, or flying horizontally and helped him determine when and how to adjust his tailplanes.

To his left was this altimeter, which indicated the altitude at which the plane was flying. Ovington favored this remarkably sensitive instrument, which he’d conducted satisfactory pre-flight tests with on the stern of an oceangoing steamship and up and down a flight of stairs.

Earle Ovington impressed crowds throughout the 1911 exhibition season, winning several major events and performing a number of publicity stunts. Among other things, Ovington became the first to write a letter in the air and the first to fly to a dinner engagement – for which he received this trophy. In the early years of aviation, nearly anything new in flight captured public interest.

Ovington boldly displayed the “unlucky” number 13 on his aircraft and flew with this mascot nicknamed Treize (French for “thirteen”). This apparent disregard for superstition had great publicity value, but it also revealed Ovington’s awareness of the inherent risk of flying. He believed that mentally preparing for the worst would improve his ability to survive if something went wrong in the air.

At a Long Island, New York, meet in September 1911, Postmaster General Frank Hitchcock had established a special airfield post office – a white tent labeled “U.S. Mail Aeroplane Station No. 1” – and set up 20 mail boxes for the crowds of enthusiastic spectators. Experiments with flying the mail had seen success in Europe, but not yet in the United States. Earle Ovington jumped at the opportunity to pilot the first U.S. Air Mail flight.

On September 23rd, 1911, Earle Ovington was duly sworn in as "Air Mail Pilot No. 1." He took off from Garden City, New York, with a 75-pound sack of letters and postcards stuffed in the cockpit of his Bleriot monoplane. Three miles away, circling above a flag-waving postmaster at Mineola, Ovington hoisted the unwieldy mailbag overboard, successfully completing the first U.S. Air Mail flight operated by the Post Office Department.

Flying the air mail would be Earle Ovington’s greatest claim to fame. After the 1911 season, Ovington retired from exhibition flying. Though he pursued other business opportunities, Ovington remained active in promoting the aviation industry – and continued to benefit from promotional sponsorships and product endorsements employing his name and reputation as "Air Mail Pilot No. 1."

Though Earle Ovington’s first short air mail flight in 1911 wasn’t much more than a publicity stunt, it previewed the beginning of regular air mail services in 1918. Flying the mail in the early years was a dangerous job. As the U.S. Air Mail Service expanded, advancing the commercial aviation industry with it, air mail pilots earned the same public admiration Earle Ovington had just a few years earlier.