Viola Gentry Lived a Life in the Clouds

Viola Gentry Photo
Image Credit: San Diego Air & Space Museum

Viola Gentry

Viola Gentry (1894-1988) was an early American aviatrix who set the first non-refueling endurance flight record for women. Gentry remained active in flying and encouraging young women to enter the field of aviation. She was a charter member of the 99s, an organization begun by 99 early aviatrix including Amelia Earhart. She received the Lady Drummond-Hay Air Trophy in 1954 for her long career promoting women in aviation. Her life was punctuated with many adventures and her passion for aviation was voracious.

1894: Viola Estelle Gentry born in Rockingham County, NC.

1910: Gentry runs away to join a circus in Greensboro.

When her circus adventure fails, the 16-year-old Gentry marries George Gee–reportedly to get away from her father and stepmother. The marriage was dissolved because of her age, and she was sent to live with family in Florida. There, without permission, Gentry took her first plane flight. Thereafter, she was fascinated with aviation. However, when Gentry landed, she was spanked for the adventure and sent home to North Carolina.[1]

1912: Gentry sent to Connecticut to live with family friends

1917: US enters WWI

1917-18: Gentry works in an ordinance factory and sells Liberty bonds to support the War.

1918: WWI ends – Gentry travels to San Francisco with American Red Cross.

1920: Witnessed stuntman land airplane on roof of the tallest hotel in San Francisco.

In California, Gentry’s enthusiasm for all things flight-related grew and grew. She attended speeches, read books, and worked two jobs saving money to take her first flying lesson. When her instructor said: ‘A woman should not fly, but should stay home, get married and raise a family.” She packed her bags and moved to New York.[2]

1924: Learns to Fly at Curtiss Field, Long Island, becoming the First North Carolina Woman to Fly an Airplane

1925: First Solo Flight

1926: Flew underneath New York City’s Brooklyn and Manhattan bridges

“The Flying Cashier,” as she was then known because of her job in a local restaurant, made front page news. Gentry achieved instant celebrity. Gentry’s parents were horrified at her exploits and felt her “activities were so unladylike that…she had disgraced the family.” She did not stop flying, though.[3]

“Viola Gentry, Brooklyn, NY, aviatrix, flirted with death when she skimmed under the Brooklyn Bridge. Bored with cashier life, she takes flier whenever she can. Here she is after daring flight as aid helped her out of flying garb.” [4]

1928: Sets the first Women’s Solo Endurance Flight Record at eight hours, six minutes and thirty-seven seconds[5]

1928: Becomes the first federally licensed female pilot from North Carolina

1929: Becomes a Charter Member of the Ninety-Nines

1929: Partners with John W. “Jack” Ashcraft

Jack and Viola teamed up to try to set a new refueling endurance flight record. The goal was to fly more than 174 hours, but tragedy intervened and they crash landed as a result of fog and an empty fuel tank. Ashcraft died instantly. Gentry’s injuries kept her in a hospital for more than a year.[6]

1931: Laundered clothes for Harold Gatty and Wiley Post when they flew around the world

1932: Welcomed Amelia Earhart back to New York after her famous flight across the Atlantic

1954: Receives the Lady Drummond-Hay Air Trophy for her support of women in aviation

1960-61: Competes in the All-Woman Transcontinental Air Race

Because of the injuries that she sustained in the 1929 crash, Viola rarely flew without a partner. So she partnered up for the All-Woman Transcontinental Air Race with with Myrtle “Kay” Thompson Cagle (also from North Carolina) who would go on to become one of the so-called Mercury 13, the group of women who trained for spaceflight at the same time as the first U.S. astronauts, but never got a chance to launch.[7]

1967: Gets First Aviation Job at History of Aviation Archives (at age 73)

After nearly 50 years as a cashier, Gentry landed her first aviation-related job in 1967, traveling the country on behalf of the University of Texas, urging her fellow Early Bird pilots to donate their records to the university’s History of Aviation archives. She was 73 years old.[8]

1975: Gentry stops flying because of cataracts.

1988: Viola Estelle Gentry dies at the age of 94.

Throughout her long life, she supported a women’s right to fly, helped preserve the history of aviation, lectured around the world, and competed in air races. And when she passed away at 94 years young, the author of her death notice proclaimed that Gentry “wanted to fly airplanes. And fly she did.”[9]

Want to Know More?

Thanks to Jennifer Bean Bower, author.

Many of the dates, stories, and facts about Viola Gentry can be found in greater detail in the book North Carolina Aviatrix Viola Gentry by Jennifer Bean Bower, published by Arcadia Publishing.

“Viola Gentry of Rockingham County, North Carolina, learned to fly in 1924 and quickly achieved greater heights. In 1925, the aviatrix took her first solo flight. The following year, she flew under the Brooklyn and Manhattan Bridges, and in 1928, she established the first officially recorded women’s solo endurance flight record. She became the first federally licensed female pilot from North Carolina that same year. She was a national celebrity, and her job in a New York restaurant secured her the nickname the “Flying Cashier.” Gentry became personal friends with fellow pioneers of aviation Amelia Earhart, Wiley Post and General James “Jimmy” Doolittle. After a near-fatal crash, Gentry focused her efforts on championing aviation for women and preserving its early history. Author Jennifer Bean Bower reveals the life of one of the great women in Tar Heel State history.”

Visit the Arcadia Website to purchase.

[1] “Viola Gentry: The Flying Cashier (1894-1988),” by Jennifer Bean Bower writing in YesWeekly, Mar 7, 2018, Updated Mar 23, 2020, Accessed September 17, 2023.

[2] Ibid, Bower, Accessed September 17, 2023.

[3] Ibid, Bower, Accessed September 17, 2023.

[4] “Aviatrix flies under Brooklyn Bridge,” New Britain herald. [microfilm reel] (New Britain, Conn.), 17 March 1926. Chronicling America: Historic American Newspapers. Lib. of Congress.

[5] “WOMAN FLIER STAYS ALOFT EIGHT HOURS; Miss Viola Gentry Says She Will Claim World’s Record for Duration Flight, New York Times, December 21, 1928. Accessed September 17, 2023.

[6] Ibid, Bower, Accessed September 17, 2023.

[7] A Female Aviator in 1926 Needed a Stunt. So She Flew Under the Brooklyn Bridge, by Rebecca Maksel writing for The Smithsonian Magazine, March 20, 2020. Accessed September 17, 2023.

[8] Ibid, Maksel, Accessed September 17, 2023.

[9] Ibid, Bower, Accessed September 17, 2023.

Scroll to Top