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Jessica Whitney Dubroff (May 5, 1988 – April 11, 1996) was a 7-year-old pilot trainee who was attempting to become the youngest person to fly a plane across the United States when, 24 hours into her flight, her small plane crashed after takeoff from Cheyenne, Wyoming.

Dubroff was born in Contra Costa, California. During her flight, which included several stopovers, Dubroff became an instant media celebrity. Her flight was vigorously followed by supporters and media outlets such as CNN, ABC, FOX and others who monitored her flight every day for the duration of her trip, reporting each time she landed or took off, until the abrupt ending of her "Sea to Shining Sea Flight."

Dubroff took off from Cheyenne in heavy rain and a sudden storm. These weather conditions contributed to the plane's crash within a few minutes of takeoff. Jessica Dubroff, her father Lloyd Dubroff, and her flight instructor Joe Reid (who was legally the pilot in command for all her flights and was apparently manipulating the controls during this particular flight) were killed in the crash. She spoke to her mother on the telephone moments before the crash with the last words, "Mom, do you hear the rain? Do you hear the rain? I just want to take off in the plane. I'm going to try to spin the plane around and do a loop."^{[cite this quote]}

The National Transportation Safety Board investigation concluded that pilot Joe Reid had made an "improper decision to take off into deteriorating weather conditions when the airplane was overweight and when the density altitude was higher than he was accustomed to, resulting in a stall caused by failure to maintain airspeed. Contributing to the pilot in command's decision to take off was a desire to adhere to an overly ambitious itinerary, in part, because of media commitments."

A book about Jessica Dubroff's life has been published by her mother, Lisa Blair Hathaway.

The accident, and its associated publicity, led to Federal legislation that prohibits anyone who does not hold at least a private pilot certificate and a current medical certificate from being allowed to manipulate the controls of an aircraft during any record attempt, aeronautical competition, or aeronautical feat.

• Report of Jessica Dubroff's flight by Avweb.com
• Probable cause report from the NTSB on NTSB.gov
• 49 U.S.C. 44724, the text of the federal law passed as a result of the accident
• AOPA perspective on AOPA.org
• Jessica Dubroff at Find A Grave