The Dole Air Race, also known as the Dole Derby, was a deadly air race across the Pacific Ocean from Oakland, California to Honolulu in the Territory of Hawaii held in August 1927. There were eighteen official and unofficial entrants; fifteen of those drew for starting positions, and of those fifteen, two were disqualified, two withdrew, and three aircraft crashed before the race, resulting in three deaths. Eight aircraft eventually participated in the start of the race on August 16, with only two successfully arriving in Hawaii; Woolaroc, a Travel Air 5000 piloted by Arthur C. Goebel and William V. Davis, arrived after a 26 hour, 15 minute flight, leading runner-up Aloha by two hours.

Of the unsuccessful six aircraft, two crashed on takeoff, two were forced to return for repairs, and two went missing during the race (Golden Eagle and Miss Doran). One of the aircraft that was repaired took off again to search for the missing aircraft several days later and also vanished over the sea (Dallas Spirit). In all, before, during, and after the race, ten lives were lost and six airplanes were lost or damaged beyond repair.