The Dole Air Race, also known as the Dole Derby, was an air race across the Pacific Ocean from northern California to the Territory of Hawaii in August 1927. Of the 18 official and unofficial entrants, fifteen drew for starting positions; 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, with only two successfully landed in Hawaii; of the other six, two crashed on takeoff, two were forced to return for repairs, and two went missing during the race. One of the aircraft forced to return for repairs took off again to search for the missing aircraft several days later and also vanished over the sea. In all, before, during, and after the race, ten lives were lost and six airplanes were lost or damaged beyond repair.

The Dole prize

Inspired by Charles A. Lindbergh's successful trans-Atlantic flight, James D. Dole, the Hawaii pineapple magnate, announced on May 25, 1927, a prize of US$25,000 for the first fixed-wing aircraft to fly the from Oakland, California, to Honolulu, Hawaii, and US$10,000 for second place. The flights would have to be completed in the 12 months following August 15, 1927. Dole stated he hoped that Lindbergh would compete.

The Honolulu chapter of the National Aeronautic Association drew up the rules for the race.

The transpacific record The publicity for the first successful transpacific flights from Oakland to Hawaii was usurped by two flights in June and July 1927, ahead of the scheduled August start for the Dole Derby. 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. An earlier attempt in 1925 had ended in failure for two Navy PN-9 seaplanes; one of the aircraft, commanded by Commander John Rodgers, ran out of fuel several hundred miles short of Hawaii and sailed to Kauai over the next nine days.

Ernie Smith and Captain C.H. Carter had arrived in Oakland earlier to attempt to parallel the Maitland/Hegenberger flight in the City of Oakland, a small Travel Air 5000 civilian monoplane, but due to mechanical difficulties, took off two hours after Maitland, and returned with a broken windshield. Unlike Lindbergh's purpose-built Spirit of St. Louis, City of Oakland had been serving as a mail carrier for Pacific Air Transport. According to Smith, Carter threatened to dump the gas after the windshield was lost, forcing the plane's return shortly after takeoff. Carter quit after the record was lost, but Smith hired Emory Bronte as a navigator, and 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 the successful June and July flights from his prizes because they had not followed his rules. The Air Corps flight had been planned months prior to the prize announcement with no intended destination other than Wheeler.

By July 22, the starting and ending points had not been set. San Francisco began developing its new municipal airport, Mills Field, in anticipation of enticing pilots into choosing it as the origin; the initial planned destination was John Rodgers Airport near Honolulu.

Contestants draw positions

The first official entrant, announced on June 28, was Arthur C. Goebel. An early entrant was Richard Grace, a Hollywood stunt pilot who shipped his plane to San Francisco shortly after wrecking his Cruzair in a Kauai to San Francisco attempt in June. Fourteen official and four unofficial entrants were announced on August 3; Grace was not part of the group. The draw for starting position in the Dole race was held on 8 August in the office of C. W. Saunders, California director of the National Aeronautics Association, at the Matson Building in San Francisco. In all, fifteen entrants made the official draw; contestants could choose to take off from Mills Field near San Francisco or Oakland Municipal Airport, but the contestants later decided the air currents at Mills were too dangerous and all aircraft were to take off from Oakland instead.

+Official and unofficial entrants and starting draw Entrant Starting Position Official / Unofficial Pilot Navigator From Drawn Mills / Oakland O Arthur C. Goebel Santa Monica, CA 9 M (1) O Maj. Livingston Irving Berkeley, CA 7 O (7) O John Augie Pedlar(w/ Miss Mildred Doran) Manley R. Lawing Flint, MI 4 O (4) O Frederick A. Giles Detroit, MI 6 O (6) O Charles W. Parkhurst Lomax, IL 3 O (3) O Lt. N. A. Goddard Lt. K. C. Hawkins San Diego, CA 2 O (2) O Arthur V. Rogers Leland A. Bryant Los Angeles, CA 14 O (11) O John W. Frost Gordon Scott San Francisco, CA 15 M (2) O Bennett Griffin Al Henley Bartlesville, OK 1 O (1) O Robert C. Fowler San Francisco, CA 10 — O Capt. J. L. Giffin Theodore Lundgren Long Beach, CA 8 O (8) O Capt. & Mrs. Wm. P. Erwin Dallas, TX 5 O (5) O Frank L. Clarke Hollywood, CA 12 M (10) O George D. Covell San Diego, CA 13 — U Martin Jensen Honolulu, HI 11 — U Robert Horseley Sarasota, FL — — U Maj. C. Usborne Vancouver, BC — — U Clair Vance San Francisco, CA — —

Trouble and confidence before the race Before the race started, many of the aircraft had mechanical issues. Pabco Flyer (Irving) broke a fuel line while conducting a test flight on August 5 from San Francisco to San Diego, and Irving was forced down in a cow pasture near Point Sur, approximately south of Monterey.  Golden Eagle (Frost/Scott) hit a gopher hole on the runway while taking off from San Diego and wrecked the landing gear and propeller. City of Peoria (Parkhurst/Lowes) was delayed by sandflies, and Bluebird (Giles) was stuck at Detroit with engine issues. 

Oklahoma (Griffin/Henley) took off on August 4 for an intended nonstop flight from Bartlesville to San Francisco, but was forced down near Amboy by a broken exhaust pipe; after effecting repairs, Oklahoma took off again at approximately 7 AM on August 5, but the aircraft came down again outside of Los Angeles due to heavy fog.

Spirit of John Rodgers (Covell/Waggener) was also forced down twice during a flight from Brea to San Diego: first near Santa Ana by fog during a test flight on August 5;  then again after an oil feed line broke on August 6, forcing the plane down at Escondido. The Tremaine Humming Bird monoplane, which was designed and built by William D. Tremaine, had a wingspan of and a low wing configuration, unusual for the time.

Meanwhile, Mildred Doran, Auggy Pedlar, and navigator Manley Lawing were flying into Oakland when their aircraft developed engine trouble due to fouled spark plugs. They successfully landed near Mendota in a wheat field in the San Joaquin Valley, but damaged the landing gear in the process and had trouble making repairs because they no longer had any tools. Doran went to Modesto, California to secure tools and a mechanic; she quipped "We threw [the tools] off at Long Beach because they were in the way and cluttering things up." Lawing was later replaced by Vilas R. Knope when Lawing could not satisfy the race committee of his navigational skills. He reportedly got lost over Oakland.

James L. Giffin announced he needed US$15,000 to complete a giant triplane under construction in July 1927; at the time, he was planning to fly it from Los Angeles to Tokyo via Hawaii. After a short test flight on August 10, Giffin confidently predicted they would rest upon arrival in Honolulu, then continue to Australia nonstop, a distance of . Giffin's intended final destination was Paris, a flight of 30 days in total via Borneo, India, Constantinople, and Rome.

Goddard had already built and tested El Encanto and anticipated it would reach speeds of at takeoff, speeding up to when nearing Honolulu as fuel was consumed, lightening the aircraft. El Encanto means "The Enchanted" and was designed by Goddard after the streamlining of a salmon.

Woolaroc, piloted by Goebel, was originally intended to carry Lieutenant W. J. Slattery as navigator. Goebel departed from Bartlesville on a nonstop flight San Francisco on August 6. In test flights before the race, Goebel's Woolaroc encountered gear issues that required Goebel to hang outside the plane to fix.

Martin Jensen and Robert Fowler competed over the purchase rights for the same Breese-Wilde Model 5; Jensen won that race after his wife Margaret raised US$15,000 from local backers in Honolulu, and Jensen took delivery of Aloha on August 8. Fowler, left without an airplane for the contest, was forced to withdraw. Because Aloha was only completed when the race was nearly about to begin, the preparations for the contest were rushed; the fuel tanks on Aloha only held and the original plan was to add sufficient spare fuel capacity via forty-nine portable containers, requiring the navigator to fill the central tank, then transfer fuel to the tank in use via a hand pump; the plane was later retrofitted with a tank, obviating the need for the complicated refueling plan, which would have required the passing of written messages between the two men.

Three days: three crashes, three dead

Two days after they drew the thirteenth position, on August 10 United States Navy Lieutenants George W. D. Covell and R. S. Waggener took off from San Diego, California in their Tremaine Humming Bird named Spirit of John Rodgers to fly to Oakland; after flying into a fog bank, the aircraft crashed into an ocean cliff at Point Loma, killing both men. Waggener had replaced Lt. Leo Pawlikowski as navigator; Pawlikowski had developed an abscess on his back which required surgery, and the doctors would not allow him to participate. William Davis, a Navy Lieutenant who would serve as the navigator for Art Goebel on Woolaroc, was granted leave to participate in the race; he had planned to catch a ride with Covell and Waggener to San Francisco, but the leave was not granted in time, and he took a train from San Diego instead.

Then, on 11 August, as J. L. Giffin and Theodore S. Lundgren approached Oakland, their aircraft, an International CF-10 Triplane, the Pride of Los Angeles, crashed into San Francisco Bay, but the two men and their passenger, Laurence Willes, were able to escape and swim to shore.

The next day, shortly after British ace Arthur V. Rogers took off for a test flight on August 12 in the twin engine Angel of Los Angeles at Western Air Express Field at Montebello, California, the aircraft reached an altitude of and began acting "queer"; Rogers jumped out of the plane as it suddenly dived towards the ground, but died as either his foot or parachute snagged on the aircraft as it crashed. Leland A. Bryant, the designer of the aircraft, was to have served as Rogers's navigator, but was not onboard during the test flight.

Withdrawals and disqualifications Maj. Livingston Irving was the first pilot to qualify for the contest. During the pre-race inspections, Major Clarence Young declared that up to ten of the fifteen entries may be disqualified for inadequate fuel capacity; the rule stated that a single-engine aircraft was required to carry of fuel, a nominal capacity of plus a 15% reserve. Another rule was interpreted to require pilots to hold commercial licenses, which five unnamed pilots did not have.