Princess Kick-a-Hole-in-the-Sky

Artwork by Reeva Wortel: Dorothy Hester smiles at center as she flies among other pioneering women pilots  

Dorothy Hester had never seen a “flying machine” of any sort. Growing up just north of Milwaukie, Oregon in the 1910s did not afford her that opportunity. Everything changed in 1926 when the 16-year-old saw a passenger balloon floating overhead. She ran after it, yelling “Gimme a ride! Gimme a ride!” as it passed by. Dorothy missed that ride, but within a year, she sat in an open cockpit waiting for liftoff. She felt the air sweep over her when the pilot started the engine and recounted later that as the plane left the ground “it was the most wonderful feeling I had ever had...I decided right then that I had found my calling.” 

Rather than finish her senior year, the teenager dropped out of high school to enroll in “ground school” and pursue her love of flying. She worked at Oregon Woolen Mills as a spinner to pay for classes but struggled to earn enough money for the flight lessons required to continue on to flight school. To help pay for the required lessons, Dorothy borrowed a parachute and caught a bus to an aviation event in Medford, Oregon. The event’s organizers offered $100 to anyone who would jump out of an airplane. Despite being “scared spitless,” she made the leap and collected her prize money. That achievement made Dorothy the first woman in the Pacific Northwest to do a parachute jump.   

Dorothy moved on to flight school at Rankin School of Flying. She continued to parachute at local air shows to pay her tuition and, as a student, became the fourth woman in Oregon history to fly solo. At graduation, legendary stunt pilot and director of the School, Tex Rankin, urged the students to continue their pursuit of a career in aviation. He spoke to the male students of opportunities to fly. And he told Dorothy, the only female student, she could work in the office. She vowed to make him eat his words. She made an appointment to fly with Tex and won him over with her flight skills. 
At age 19, she was made a life member of the Women’s International Aeronautical Association. Two years later, Dorothy was barnstorming and performing as a pilot with Tex Rankin’s Flying Circus, earning the grand name, “Princess Kick-a-Hole-in-the-Sky.” Dorothy’s flare for outside loops and snap rolls won her acclaim as she barnstormed across the country. Throughout her career, she continued to tear down barriers for women in the field of aviation. As a 38-year old mother of two children, Dorothy became the first woman to take the US Navy’s G-Force test, forerunner to the tests given to the first astronauts. After retiring in 2004, she was inducted into the World Aerobatic Club Hall of Fame. 

Dorothy, along with many other Rankin School pilots (as well as Tex himself), frequently made landings in Beaverton at Bernard’s Airport, which was a short hop from Rankin’s airport at Swan Island in North Portland.