The Dole Air Race, the Two Thousand Four Hundred Miles of Open Pacific, and the August of Nineteen Twenty-Seven That Nobody in Oakland Could Forget

In August 1927, three months after Charles Lindbergh’s solo Atlantic crossing rewired the American imagination, a California pineapple magnate offered $25,000 to the first pilot to fly nonstop from Oakland to Hawaii. What followed was equal parts triumph and catastrophe. Of the eight aircraft that left Oakland’s runway on August 16, 1927, only two reached Wheeler Field on Oahu. Seven people died.

Why James Dole Offered $25,000 to Cross the Pacific

James Dole was not a pilot. He was the founder of the Hawaiian Pineapple Company, and by 1927 his product was on grocery shelves across the mainland. The problem was perception. Most Americans regarded Hawaii as impossibly remote - a destination requiring weeks aboard a steamship and considerable wealth.

Three weeks after Lindbergh’s Paris landing, Dole announced his prize: $25,000 to first place, $10,000 to second, for a nonstop flight from Oakland, California, to Wheeler Field, Oahu. The straight-line distance was approximately 2,400 miles of open ocean with no land beneath you if the numbers came out wrong.

He called it the Dole Derby. The response was immediate.

The Rush to Enter - and the Deaths Before the Race Even Started

This was the summer when aviators were the biggest celebrities in America. Lindbergh had opened the floodgates. Within weeks, nearly forty entries had poured in from across the country - some from experienced pilots, some from men barely qualified to attempt such a crossing.

The National Aeronautic Association, certifying the entries, grew alarmed. They imposed requirements: aircraft had to demonstrate a minimum range of 2,700 miles under fuel load, navigators had to pass qualification tests, and survival equipment was mandatory. But in the gold rush atmosphere of that summer, the rules had a hard time keeping pace with the ambition.

Before the race began, pilots started dying. Training flights went wrong. Overloaded aircraft failed to clear obstacles on takeoff. Engines quit on test runs. At least two aircraft were destroyed in pre-race crashes, their pilots killed or badly injured. The newspapers that had breathlessly celebrated the Derby began running editorials pairing the word reckless alongside the word heroic.

The race was originally scheduled for August 12. Weather and mechanical delays pushed it to August 16. By then, the original field of nearly forty had been reduced - by crashes, failures, and disqualifications - to eight aircraft deemed ready to fly.

The Eight Aircraft on the Oakland Ramp

On the morning of August 16, thousands of spectators crowded Oakland Municipal Airport. Newsreel cameras rolled. Families gathered to watch their sons, their husbands, and in one case a daughter, head west over the water.

The Woolaroc was a Travel Air monoplane backed by Phillips Petroleum money. Its pilot, Art Goebel, was an air show performer known for quiet precision under pressure. He had personally selected his navigator, William Davis, for his celestial navigation skills, and the two had rehearsed their procedures together. The Woolaroc was methodically prepared.

The Aloha, a Breese monoplane, was flown by Martin Jensen, a pilot who actually lived in Hawaii. Jensen knew the prevailing winds and understood the island approaches intimately. His navigator was Paul Schluter. Of all the crews on that ramp, Jensen and Schluter carried the most specific knowledge of what waited at the far end.

The Miss Doran was a Buhl trimotor carrying Mildred Doran, a 22-year-old schoolteacher from Flint, Michigan. She was not simply a passenger. She held a pilot’s license and had lobbied hard for a place on the crossing. The aircraft had been named for her, and she had been selected - after considerable press attention - to become the first woman to attempt the Pacific by air. The press called her the Flying Schoolteacher. When reporters asked about the risks, she answered honestly. She went anyway. The plane also carried pilot John Pedlar and navigator Vilas Knope.

The Golden Eagle, a Lockheed Vega, carried pilot Jack Frost and navigator Gordon Scott. The Vega was one of the genuinely beautiful designs of the era - a high-wing monoplane with a clean plywood monocoque fuselage, fast for its day. On paper it was among the stronger entries in the field.

Four more aircraft completed the starting lineup.

What Dead Reckoning Over Open Ocean Actually Meant

Shortly after noon, Art Goebel advanced the throttle in the Woolaroc, rolled down the runway, lifted cleanly, banked west, and disappeared into the haze over San Francisco Bay. One by one, the other seven followed. And then the ocean closed behind them.

For the next twenty-six hours, there was nothing. No radio contact that could confirm positions. No sightings from ships in the crossing corridor. Just the Pacific, and eight small airplanes somewhere in the middle of it.

Navigation in those cockpits meant a compass, an airspeed indicator, and a clock. Radio direction finders existed but worked intermittently at best, and the signal from Hawaii at that range was weak. The primary tool was dead reckoning: you knew your heading, your airspeed, and your elapsed time. You did the arithmetic and flew the resulting line.

The problem was that small errors compounded without mercy. An undetected wind shift could push an aircraft five or ten miles off course in a single hour. A slight compass deviation, uncorrected. A small error in airspeed estimation. Over 2,400 miles, those errors multiplied. An arithmetic error of three degrees didn’t put you at Oahu - it put you at empty water, with no fuel remaining to search for the island chain somewhere below the horizon.

The ocean provided no feedback. No towns, no rivers, no terrain features, nothing to confirm whether you were on course or drifting invisibly away from it. Some navigators carried sextants and could shoot celestial fixes when the sky cooperated. Davis on the Woolaroc used his well. But the August Pacific was not always cooperative.

Goebel Wins - and Four Aircraft Don’t Arrive

Art Goebel landed the Woolaroc at Wheeler Field 26 hours and 17 minutes after leaving Oakland. He climbed from the cockpit with the composure of a man who had planned carefully and executed the plan. Martin Jensen brought the Aloha in approximately two hours later, taking second place and the $10,000 prize.

Two airplanes. Both prize positions claimed.

But only two had arrived.

Two other aircraft had turned back before ranging too far from the California coast, landing safely with mechanical problems. That left four aircraft unaccounted for: the Miss Doran, the Golden Eagle, and two others. Hours stretched out. Night fell over Wheeler Field. The Pacific was silent.

The Search and the Compounding Disaster

The search began the next morning. The Navy committed ships. Aircraft began flying grid patterns. Volunteer pilots joined in. And here is where aviation disasters sometimes compound themselves - one loss leading to another in the act of trying to repair the first.

William Erwin had flown an aircraft called the Dallas Spirit in the race. He had turned back safely before ranging too far from shore. Now, with four aircraft missing, Erwin volunteered to return to the search area. He refueled, loaded his radio operator, and departed.

Shortly after departure, the radio operator aboard the Dallas Spirit began transmitting fragmentary messages. Something had possibly been sighted. The signals grew weaker. Then they stopped entirely. The Dallas Spirit was never found.

When the Navy formally ended the search, the accounting was devastating:

John Pedlar, Vilas Knope, and Mildred Doran - gone with the Miss Doran
Jack Frost and Gordon Scott - gone with the Golden Eagle
William Erwin and his radio operator - gone with the Dallas Spirit

Seven people, either racing or volunteering to help, taken by the Pacific without a trace.

What the Dole Race Exposed About 1927 Aviation

The newspapers turned hard. The same press that had celebrated the Dole Derby as a grand American adventure was now calling it a carnival of recklessness. James Dole, who had offered the prize in genuine good faith, was devastated and never again associated himself with anything similar. The word Derby, which had sounded festive in June, carried different weight by September.

The race exposed, in the most unforgiving terms possible, exactly what transoceanic overwater flying required that 1927 aviators simply did not yet have:

Reliable radio navigation
Standardized oceanic weather forecasting
Mandatory survival equipment capable of actually keeping crews alive at sea
Communication protocols so aircraft could report positions over water and rescuers could calculate where to search when they went silent

How the Lessons Shaped Pacific Aviation

None of these improvements came from a single event. They accumulated from the weight of disasters like this one, absorbed by an industry that asked hard questions and then tried to build something better.

Pan American Airways, which launched Pacific mail service in 1935 and passenger service shortly after, built its procedures on hard-won lessons from exactly this era. The Clipper routes - the island chain stepping stones, the refueling stops at Wake and Midway, the navigation training standards for oceanic crews - have roots in the summers when aviation was still learning what the ocean would and would not forgive.

Where the Woolaroc Is Today

The Woolaroc survives. It sits today at the Woolaroc Museum in Bartlesville, Oklahoma, and it is worth the drive if you are anywhere near northeast Oklahoma.

It is a modest-looking airplane in person. Clean lines, nothing elaborate. You stand in front of it and try to imagine two men inside it for 26 hours - shooting celestial fixes, working dead reckoning arithmetic, holding their heading through the night over open Pacific with no autopilot, no satellite, no terrain awareness, and no one to call if anything went wrong.

That is what the golden age of aviation was, at its best and its worst. Ordinary-looking airplanes doing extraordinary things, flown by people who decided something was worth attempting and then attempted it with everything they had.

Key Takeaways

The Dole Air Race took place on August 16, 1927, three months after Lindbergh’s Atlantic crossing, with $25,000 offered for a nonstop flight from Oakland to Hawaii - approximately 2,400 miles of open Pacific
Of eight starters, only two finished: Art Goebel in the Woolaroc (26 hours, 17 minutes) and Martin Jensen in the Aloha
Seven people died: the crews of the Miss Doran, the Golden Eagle, and the Dallas Spirit, which was lost during the subsequent search
The race exposed critical gaps in 1927 overwater aviation: no reliable radio navigation, no oceanic weather standards, no meaningful survival equipment, and no position-reporting protocols
The hard lessons from the Dole Race and similar disasters directly shaped the safety standards that made Pan American’s Pacific Clipper service viable by the mid-1930s
The Woolaroc is preserved at the Woolaroc Museum in Bartlesville, Oklahoma