The first air race was the Bennett Race, flown way back in 1909, at Rheim, France. The lone American entry was Glenn Curtiss who had his eye on the Gordon Bennett Trophy. Curtiss set a new world record at the magnificent pace of 56.5 miles per hour, by beating his closest completion, Frenchman Louis Bleroit by a mere 6 seconds. Curtiss won the top two prizes. He not only succeeded in wining the James Gordon Bennett trophy that he had coveted, for the fastest two laps, but garnered the Prix de la Vitesse Trophy for the fastest three laps as well.

The first air race in the United States was held in Los Angeles in October, 1910, followed closely by a second meet sponsored by the Aero Club of America at Belmont Park in Elmont, New York. Another racing first was The Jacques Schneider Trophy Race initiated in 1913 for seaplane races. Like all the other early races, it was suspended during World War I but resumed again after the war. Another important early air race was the Michelin Cup, for the longest flight between sunrise and sundown in a single day. The first Michelin Cup was won by Orville Wright in 1908.

Not all prizes were for competitive racing. Many were to entice pilots to fly for other reasons, such as the $50,000 prize William Randolph Hearst offered in 1911 for the first pilot who could fly across the U.S. in 30 days or less. This prize inspired Cal Rodgers to make the first transcontinental flight. However, he did not win the money as it took him 49 days and 19 crashes to complete the flight.

After World War I, several major trophies and prizes were established. One was the London Daily Mail prize of 10,000 pounds offered by Lord Northcliffe, for the first non-stop flight between England and America. The prize was claimed by two former British military pilots, Alcock and Brown, in 1919. Another prize offered in 1919 by New York hotel owner Ramond Orteig, was a $25,000 prize for the first person to fly across the Atlantic. A number of pilots attempted the crossing, some never to be heard from again. This prize was not claimed for eight long years until Charles Lindbergh made his historic flight in 1927.

As the years progressed into the 1930s, air racing picked up speed. A number of large purses were offered to encourage the development of faster and better aircraft. Many of the early racers were designers and builders, as well as pilots. The race team of James Wendell and Harry Williams is a good example of the best of designer and businessman. Their race planes dominated the air race circuit for some five years in the 1930s. The Wedell-Williams unlimited class racers won fourteen distinguished finishes in the Thompson and Bendix Trophy Races.

There were, and still are, two different types of air racing. One is "pylon" or closed-circuit racing where airplanes fly in a small circle of a few miles or less. The other is cross-country racing over many miles. In pylon racing, airplanes can be modified to get as much speed out of the airplane as you can build into it. In cross-country racing, airplanes must be stock just as they were originally built. Cross-country races are from several hundred miles to several thousand miles long.