The Wright Brothers made many attempts at flight, starting in 1900 on gliders (1). In these endeavors, the brothers managed to develop their piloting skills enough. The glider with which they made history was originally tested on December 14, 1903, staying airborne for roughly three seconds before crashing, which required repairs (2). The first successfully executed powered flight of all time took place just three days later, on December 17, at Kill Devil Hills, NC (then called Kitty Hawk). It lasted 12 seconds and covered a span of 120 feet, with an airspeed of 34 miles per hour (3). Orville was the pilot.
There was a headwind of 21 (sometimes reported as 27) miles per hour, but the brothers switched off and flew three additional times. Their longest flight lasted 57 seconds. However, after the final flight, the glider blew over and was damaged enough that it could never be used again (4). The famous telegraph that Orville sent to his family is pictured below.
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(1) Benson, Tom, ed. "Overview of the Wright Brothers Invention Process." NASA. Last modified June 12, 2014. Accessed May 16, 2016. http://wright.nasa.gov/overview.htm.
(2) National Air and Space Museum. "The Wright Brothers: The Invention of the Aerial Age." Smithsonian National Air and Space Museum. Accessed May 16, 2016. https://airandspace.si.edu/exhibitions/wright-brothers/online/fly/1903/designing.cfm
(3) First Flight Society. "The Wright Brothers." First Flight Society: Preserving the Legacy of the First Flight and Sharing the Genius of the Wright Brothers for the Future. Accessed May 16, 2016. http://firstflight.org/learn/the-wright-brothers/.
(4) The Library of Congress. "The Dream of Flight." Last modified July 29, 2010. Accessed May 16, 2016. https://www.loc.gov/exhibits/treasures/wb-achieve.html.
(2) National Air and Space Museum. "The Wright Brothers: The Invention of the Aerial Age." Smithsonian National Air and Space Museum. Accessed May 16, 2016. https://airandspace.si.edu/exhibitions/wright-brothers/online/fly/1903/designing.cfm
(3) First Flight Society. "The Wright Brothers." First Flight Society: Preserving the Legacy of the First Flight and Sharing the Genius of the Wright Brothers for the Future. Accessed May 16, 2016. http://firstflight.org/learn/the-wright-brothers/.
(4) The Library of Congress. "The Dream of Flight." Last modified July 29, 2010. Accessed May 16, 2016. https://www.loc.gov/exhibits/treasures/wb-achieve.html.