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.
Of the 15-18 airplanes entered, eleven were certified to compete but three crashed before the race, resulting in three deaths.
The race began on 16 August 1927. The fifteen competitors were seen off by a crowd estimated to include 75,000 to 100,000 persons. 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.