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in the flying game and Fowler began to make plans to enter the $50,000 Hearst Transcontinental Flight contest for the first aviator to fly from coast to coast in thirty days. 

He organized a group of ten sponsors for the flight, headed by wealthy west coast W. F. Grundy, and J. J. Cole, owner of the Cole Motor Car Company of Indianapolis, Indiana. A new Wright aeroplane was ordered with spare parts, and Fowler was the first to formally enter the contest. He arrived in Dayton about July 1st, 1911, where he became a rather "special" student, having arranged to thoroughly learn all the details of the plane and engine, in addition to taking flying instruction. He intended to become well qualified both as a pilot and mechanic. He purposely put off learning to fly until he completely understood the plane and all its working parts in every way. For some time Fowler put in long hours in the Wright factory helping to build and assemble every piece and part of his plane and engine, then started flying lessons from Instructor Al Welsh, with some special attention from Orville Wright. He was an unusually apt pupil and caught on quickly, making his first solo flight on his birthday, August 10th, 1911.

After very little practice Fowler shipped his plane to the west coast with three engines and a quantity of spare parts to prepare for the start of his flight across the continent. The plane had two standard fuel tanks, a 7-hour supply, and Wright factory mechanic R. G. Howland accompanied the shipment. Fowler chose as his mechanics and assistants Ralph Newcomb and Frank Murray of San Francisco, and J. A. Passfield of Los Angeles. It first appears that Fowler would be competing with seven other aviators in the coast-to-coast race, but actually only two others really started. Fowler was first to leave on September 11th, James Ward started from Governors Island, New York on September 13th and Cal Rogers from Sheepshead Bay, Long Island, New York on September 17th. After a series of mishaps Ward gave up the trip on the evening of the 14th at Addison, New York.

Fowler officially started his flight from the Stadium, Golden Gate Park, San Francisco. Circling, he gained an altitude of about 1500 feet, which was over twice as high as he had ever been. He then started off on his eastward course.