Cliff Robinson is a second generation aviator and barnstormer. His father, Frank Robinson, was a successful aviator in his own right. Flying the family's airplanes from their country airstrip in Lamb, Ind., Frank taught Cliff how to fly, and at the age of 16, Cliff flew an airplane by himself for the first time. An aerobatic pilot, crop duster, flight instructor, and real-estate broker, Cliff has now logged over 8,000 hours of combined flight time, in dozens of different types of modern and vintage aircraft.

When Cliff originally learned aerobatics, it was not a matter of providing entertainment but a matter of safety. His father believed that all pilots should know how to do aerobatics in the event they found themselves flying at an unfavorable angle. In addition to aerobatic thrill rides and air show performances, Cliff also provides aerobatic instruction and upset recovery training to pilots wishing to improve their skills.

Cliff Robinson has performed in virtually every capacity a pilot can work, including commercial flights, crop dusting, aerobatic showmanship and flight instruction. Operating out of the Madison Municipal Airport, he is often seen taking passengers on rides over the Jefferson County area in his Super Stearman biplane. He has given more than a thousand rides in the last 12 years, and has flown under the Madison-Milton bridge more than once during his aerial demonstrations.

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In 2022, Cliff was awarded the prestigious FAA Wright Brothers Master Pilot Award for his fifty plus years of aviation experience.