The Dole Air Race was a competition to cross the Pacific Ocean by air. 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 airplane to fly the 3870 kilometers (2400 miles) from Oakland, California to Honolulu, Hawaii, and US$10,000 for second place.

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.

However, the honor of being the first to make a trans-Pacific flight had already been earned, twice over. On 28 June, about a month after Dole posted the prizes, United States Army Lieutenants Lester J. Maitland and Albert F. Hegenberger flew a three-engine Fokker military airplane from Oakland Airport to Wheeler Army Airfield on Oahu in 25 hours and 50 minutes. Then, on 14 July, Ernie Smith and Emory Bronte, took off from Oakland in the City of Oakland, a small civilian monoplane, and, upon running out of fuel 26 hours and 36 minutes later, crash-landed in a thorn tree on Molokai. Dole disqualified both of them from his prizes because they did not land in Honolulu.

The drawing 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, in the Matson Building in San Francisco, California.

Two days after the drawing, United States Navy Lieutenants George D. Covell and R. S. Waggener took off from San Diego, California, to fly to Oakland, flew into a fog bank, crashed into an ocean cliff, and died. The next day, Arthur V. Rogers took off for a test flight at Western Air Express Field at Montebello, California, circled, came about to land, suddenly dived into the ground, and died.

Meanwhile, Mildred Doran, Auggy Pedlar, and Vilas R. Knobe were flying into Oakland when their airplane developed engine trouble. They successfully landed in a wheat field in the the San Joaquin Valley, but had trouble making repairs because they no longer had no tools. Doran was quoted as stating, "We threw them off at Long Beach because they were in the way and cluttering things up."

Then, on 11 August, as J. L. Giffin and Theodore S. Lundgren approached Oakland, their airplane crashed into San Francisco Bay. The two men were unhurt, though.

By 16 August, the starting lineup had diminished to eight:

• Golden Eagle, a Lockheed monoplane flown by Jack Frost and navigated by Gordon Scott
• Aloha, a monoplane flown by Martin Jensen and navigated by Paul Schluter
• Woolaroc, flown by Art Goebel and navigated by William V. Davis Jr.
• Miss Doran, flown by Auggy Pedlar, navigated by Vilas R. Knobe, and carrying Mildred Doran
• Oklahoma, a sister ship of Woolaroc, piloted by Bennett Griffin and navigated by Al Henley
• Dallas Spirit, flown by William P. Erwin and navigated by Alvin Eichwaldt
• El Encanto, a metal monoplane flown by Norman A. Goddard and Kenneth C. Hawkins, which was heavily favored in the pre-race odds
• Pabco Flyer, flown alone by Livingston Irving

Just before 11am, Oklahoma took off. She was followed by El Encanto, which had not cleared the runway before she swerved and crashed. Pabco Flyer lifted momentarily into the air, then crashed some 7000 feet from the runway. Their crews were not hurt.

Golden Eagle took off smoothly and flew out of sight.

Miss Doran succeeded in taking off, but circled back and landed less than ten minutes later. Oklahoma made it further, but over San Francisco her crew aborted the flight. Then Dallas Spirit returned to Oakland.

Aloha and Woolaroc took off uneventfully, and Miss Doran succeeded on her second attempt. Pabco Flyer also tried again, and crashed again.

Wollaroc won the race in 26 hours, 17 minutes, earning Goebel and Davis US$25,000. Aloha arrived in 28 hours, 16 minutes, earning Jensen and Schluter US$10,000. Neither Golden Eagle nor Miss Doran were ever seen again.

The search for them was aided by the submarines USS R-8 (SS-85), USS S-42 (SS-153), and S-46 (SS-157). In addition, after repairing Dallas Spirit, Erwin and Eichwaldt from Oakland for Honolulu to search the route. They were never seen again, either.