The Deadly Dole Air Race

The Dole Air Race of August 16, 1927 was from Oakland, California, to Honolulu, Hawaii, for a prize of $35,000. Fifteen planes were registered. Eleven qualified to start. Two crashed on the way to the starting point, and another crashed during a test flight before the race. Things only got worse once the race began.
On the morning of August 16, the eight remaining planes queued up for their opportunity. They drew lots for flight order and took off one by one. As people cheered, things went bad in a hurry.

One plane, the El Encanto, simply shot off the edge of the runway, and tumbled over her wing. Another the Pabco Flyer got into the air... until she didn't, landing some 7000 feet away in a marsh. Three more planes took off only to promptly return with technical difficulties.

Of the fifteen planes that had entered the race, only four planes, the Golden Eagle, Aloha, Woolaroc, and Miss Doran, were actually able to attempt the journey. The results of the ill fated race would soon be known.

The carnage didn't stop there. Nor did it stop once the race was over. Read more about the deadly Dole Air Race at Atlas Obscura blog. This story is part of a regular feature they call Morbid Monday. Link

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My grandfather was the navigator on the Woolaroc. The story of the race can be found in the book "glory gamblers".

He went on to a great naval career. He was on a Navy flight demonstration team called the "Three Seahawks". They would tie their aircraft together and perform aerobatics. This later morphed into the Blue Angles.

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