Women's History Month Feature | Viola Gentry: The Flying Cashier Who Made Aviation History

She set the first non-refueling endurance flight record for women. She flew under the Brooklyn Bridge for fun. She was a cashier who saved up three weeks' wages at a time just to pay for a single flying lesson. Viola Gentry's story is one of sheer, stubborn determination, a woman who refused to be grounded by poverty, injury, or the countless men who told her she simply shouldn't fly. For women's history month, let's take a deeper look at the history of the flying cashier.

A Rebel from the Start

Viola Estelle Gentry was born in Rockingham County, North Carolina, in 1894. Life at home was difficult, and by the age of 16 she had already run away to join the circus, gotten married, and divorced. Her family sent her to live with relatives in Florida, hoping it would calm her down.

It didn't.

While in Florida, a young Gentry snuck onto an airplane for her first flight and was reportedly given a sound spanking when she landed. It didn't matter. Something had awakened in her that no amount of discipline could extinguish.

Saving Up to Reach the Sky

Flying in the 1920s was a sport reserved for those with deep pockets. Gentry had none. She worked two low-paying, monotonous jobs to save money for flying lessons, one of them as a cashier at a restaurant, which earned her the nickname "The Flying Cashier" in the newspapers. The cost of one flying lesson was the equivalent of about three weeks' wages. 

But when she wasn't working, she was at the airport, talking to pilots and mechanics, studying engines, absorbing everything she could. She learned to fly in 1924 and took her first solo flight in 1925. She became the ninth American woman to receive a pilot's license from the U.S. Department of Commerce. 

Flying Under the Brooklyn Bridge

In 1926, Gentry flew underneath the Brooklyn and Manhattan bridges. The stunt was front page news, and she became an instant celebrity. Not everyone was thrilled, according to relatives, her family felt her activities were so unladylike that she had disgraced them. Gentry, characteristically, kept flying.

Breaking Records

In December 1928, Viola Gentry did something no woman had done before. She flew for 8 hours, 6 minutes, and 37 seconds, setting the first non-refueling endurance record for women.  It was a landmark moment in aviation history, proof that women belonged in the cockpit just as much as anyone else.

The record was eventually broken, and Gentry set her sights on reclaiming it. In July 1929, she attempted another endurance flight.  It ended in disaster. Her aircraft crashed in a field on Long Island, killing her co-pilot and leaving Gentry with a fractured skull and crushed shoulders. She spent more than six months recovering in hospital.

Grounded but Never Gone

The crash could have ended everything. For a time, it did end her solo flying career. Gentry eventually returned to aviation, though she always flew with another pilot to compensate for her injuries.  She went back to work as a cashier. She kept showing up.

In 1954, she received the Lady Drummond-Hay Air Trophy for her long career promoting women in aviation. In 1960 and 1961, she competed in the All-Woman Transcontinental Air Race, still flying, still competing, well into her sixties.

Then, near the end of her life, she took on what may have been her most important role of all: traveling the country on behalf of the University of Texas, urging fellow early aviators to donate their records, photographs, logbooks, and memoirs to the university's History of Aviation archives. She was 73 years old and it was her first aviation-related job. The collection she helped build became an invaluable historical resource.

She also self-published a memoir, Hanger Flying, recounting the personalities of the early pilots she had known personally, including Amelia Earhart and Charles Lindbergh.

A Life Fully Lived

Viola Gentry died on June 23, 1988, at the age of 94. She had spent nearly a century defying expectations, of her family, of her era, of anyone who thought a cashier from North Carolina had no business reaching for the sky.

Her story is a reminder that aviation history wasn't made only by the wealthy and the famous. Sometimes it was made by someone who simply saved up enough for one more lesson, climbed into the cockpit, and refused to come down.

Read more about Viola in our book North Carolina Aviatrix Viola Gentry.

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