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16th Century when Leonardo da Vinci researched the flight of birds and designed several flying machines based on the mechanisms he observed. His work survives in the "Codex on the Flight of Birds." As fascinating as these works may be, as far as we know, no successful flying machine was built from them.
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Jean-Marie Le Bris achieved flight with a glider pulled by a horse. You can see him in the photograph from 1868
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George Cayley investigate and document the forces of flight (weight, lift, drag, and thrust) and develop the concept of the airplane as a fixed-wing machine with systems for lift, propulsion, and control. He designed and built several models, including successful gliders. His work, however, was limited by a lack of engine power or lightweight components. Nevertheless, what he designed had a lot of similarities with later powered aircraft, including the main wing and tail stabilizers.
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1886, another French aviator, Clement Ader, built a steam-powered airplane known as 'Eole.' This had partial success, achieving flight off the ground of about 50 meters.
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Wilbur and Orville Wright spent four years of research and development to create the first successful powered airplane, the 1903 Wright Flyer. The aircraft only flew 37 metres and stayed airbone for just 12 seconds.
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The longest test flight in 1905 lasted 39 minutes and covered over 38 kilometres