16 August 1927: Not long after Charles A. Lindbergh had flown solo across the Atlantic Ocean, James D. Dole, founder of the Hawaiian Pineapple Company (HAPCO, now the Dole Foods Company, Inc., Westlake Village, California) offered a prize of $25,000 to the first pilots to fly from Oakland Field, Oakland, California, to Wheeler Field, Honolulu, Oahu, Territory of Hawaii. A $10,000 prize was offered for a second-place finisher. There were 33 entrants and 14 were selected for starting positions. After accidents and inspections by the race committee, finalists were down to eight.
Accidents began to claim the lives of entrants before the race even began. A Pacific Aircraft Company J-30 (also known as the Tremaine Hummingbird) flown by Lieutenants George D. Covell and Richard S. Waggener, U.S. Navy, named The Spirit of John Rodgers, crashed into the cliffs of Point Loma in heavy fog 15 minutes after takeoff from North Island Naval Air Station, San Diego, California, enroute to Oakland Field. Both naval officers were killed. They had drawn starting position 13. Arthur V. Rogers was killed after takeoff from Montebello, California, in his Bryant Monoplane, Angel of Los Angeles. One airplane, Miss Doran, made an emergency landing in a farm field, and a fourth, Pride of Los Angeles, crashed into San Francisco Bay while on approach to Oakland. The occupants of those two airplanes were unhurt.
By the morning of 16 August, there were eight entrants. There starting positions had been selected by a random draw. A little before 11:00 a.m., the first airplane, a Travel Air 5000, registered NX911 and named Oklahoma, took off but soon aborted the flight because of engine trouble. El Encanto, a Goddard Special, NX5074, crashed on takeoff. A Breese-Wilde Monoplane, Pabco Flyer, NX646, crashed on takeoff. The crews of these three airplanes were not hurt.
The next airplane to take off was Golden Eagle, the prototype Lockheed Vega. Registered NX913, it was flown by Jack Frost with Gordon Scott as the navigator. It soon disappeared to the west.
Next off was the Buhl CA-5 Air Sedan, NX2915, named Miss Doran. Repairs from its unscheduled landing in the farmer’s field had been accomplished. It was flown by John “Auggy” Pedlar with Lieutenant Vilas R. Knope, U.S. Navy, as navigator. Also aboard was a passenger, Miss Mildred Doran, the airplane’s namesake. She was a 23-year-old fifth-grade school teacher from Flint, Michigan, who knew William Malloska, owner of the Lincoln Petroleum Company (later, CITGO) and convinced him to enter an airplane in the Dole Air Race and allow her to fly along. Two local air circus pilots reportedly flipped a coin for the chance to fly the airplane. Auggy Pedlar won the toss. Just ten minutes after takeoff from Oakland Field, Miss Doran returned with engine problems.
Next off was Dallas Spirit, a Swallow Special, NX941, with William P. Erwin, pilot and Alvin H. Eichwaldt, navigator. It also quickly returned to Oakland.
The last two entrants, a Breese-Wilde 5 Monoplane, NX914, Aloha, with Martin Jensen, pilot, and Paul Schluter, navigator, and Woolaroc, a Travel Air 5000 took off without difficulty.
Miss Doran made a second attempt and took off successfully. Pabco Flyer also tried again, crashing a second time.
Woolaroc, with Arthur C. Goebel as pilot and William J. Davis, Jr., as navigator, flew across the Pacific and arrived at Honolulu after 26 hours, 17 minutes, to win the race. Aloha arrived after 28 hours, 16 minutes.
Golden Eagle and Miss Doran never arrived. A search by more than forty ships of the United States Navy was unsuccessful. Dallas Spirit was repaired and Erwin and Eichwaldt took off to join the search for their competitors. They, too, were never seen again.