The Dole Air Race, also known as the Dole Derby, was a tragic air race across the Pacific Ocean from northern California to the Territory of Hawaii in August 1927. Of the 15-18 airplanes entered, eleven were certified to compete but three crashed before the race, resulting in three deaths. Eight eventually participated in the race, with two crashing on takeoff and two going missing during the race. A third, forced to return for repairs, took off again to search for the missing and was itself never seen again. In all, before, during, and after the race, ten lives were lost and six airplanes were total losses. Two of the eight planes successfully landed in Hawaii.
Inspired by Charles A. Lindbergh's successful trans-Atlantic flight, James D. Dole, the Hawaii pineapple magnate, put up a prize of US$25,000 for the first fixed-wing aircraft to fly the 3,870 kilometers (2,400 mi) from Oakland, California to Honolulu, Hawaii, and US$10,000 for second place.
The first transpacific flight had already taken place, twice over. On 28 June, about a month after Dole posted the prizes, Air Corps Lieutenants Lester J. Maitland and Albert F. Hegenberger flew a three-engine Atlantic-Fokker C-2 military aircraft from Oakland Municipal Airport to Wheeler Army Airfield on Oahu in 25 hours and 50 minutes. Ernie Smith and Captain C.H. Carter had arrived earlier for the attempt, but due to mechanical difficulties, took off two hours after Maitland, and returned with a broken windshield. Carter quit after the record was lost, but Smith hired Emory Bronte as a navigator, and the City of Oakland, a small Travel Air 5000 civilian monoplane, took off again on July 14. Upon running out of fuel 26 hours and 36 minutes later, they crash-landed in a thorn tree on Molokai. Dole disqualified both of them from his prizes because they did not land in Honolulu (the Air Corps flight had been planned months prior to the prize announcement and had no intent to land other than at Wheeler).