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

This is a long one, but such a fantastic story that connects to our McMenamins Cedar Hills Pub. Accompanying the story is a just-finished mural by artist Reeva Wortel that will hang in the new Cedar Hills Pub, scheduled for its grand opening in Fall 2017.

Dorothy Loretta Hester was born September 14, 1910, in Ardenwald, north of Milwaukie, OR, the fourth daughter of an Irish house painter. Dorothy’s mother Margaret died when Dorothy was nine years old, leaving her father, William J. Hester, to care for five rambunctious daughters, the youngest still a baby. Mr. Hester had built a small house on a piece of land with some fruit trees where the family could have a cow. Entertainment for the children was hearing their father play musical instruments, and Dorothy decided she wanted to be a dancer and travel with a troupe of entertainers. Dorothy and her sisters persisted in running off every housekeeper their father brought home.

In 1926, Dorothy Hester had yet to see an airplane. When she was 16, a balloon passed low over town, headed north toward Portland. Dorothy ran after the balloon yelling, “Gimme a ride! Gimme a ride!” Soon she learned there was an airport in Portland where she could pay for an airplane ride. On October 9, 1927 Dorothy set out alone on the street car for Portland and rode to the end of the line. When she got off, she saw airplanes flying, and started running, afraid they would all crack up or run out of gas before she got her ride, none of which happened. That day, as Dorothy sat in the open cockpit, she felt the rush of air sweep over her when the engine started. She recalled, “When we lifted off the ground, my heart swelled and I felt like I was in heaven. It was the most wonderful feeling I had ever had, and I decided right then that I had found my calling.”

When the plane landed, a salesman approached her. She said, “If I were a boy, I would certainly learn to fly.” The salesman assured her that if she wanted to learn to fly, the Rankin School of Flying would gladly teach her. The fact that she was a girl, barely 17, with no money, didn’t slow Dorothy up for long.

A month later, November 1927, she enrolled in ground school. She dropped out of her senior year of high school for another kind of education. To pay the $250 fee for ground school, Dorothy went to work at the Oregon Woolen Mills as a spinner, earning 63 cents an hour. At a time when butter cost 15 cents a pound and no one had much money, earning funds to pay for flying lessons seemed impossible. Dorothy’s father thought the idea would be short lived and her sisters bet her $10 that she would never solo. During the fall, winter, and spring, Dorothy worked all day at the woolen mill and then rode the streetcar to Swan Island in North Portland for ground school, which lasted three hours.

That year, she heard that the American Legion Convention in Medford was offering $100 to anyone interested in making an exhibition parachute jump. Hester borrowed a parachute and caught a bus to Medford with her sister. The convention’s last attraction for the day was Dorothy’s jump. The plane reached altitude and Dorothy made her way onto the wing and froze, as she put it, “scared spitless.” The pilot circled while yelling, “Jump, jump!” Finally, he walloped her hand with a fire extinguisher and she jumped.  Enjoying the freedom, she safely landed in an orchard and collected her $100. She was the first woman in the Pacific Northwest to make a parachute jump.

Dorothy learned to fly the following year, at the age of 17, and worked her way through flight school by parachuting at local air shows for money. She was soloed by Elrey Jeppesen at the Rankin School of Flying; she was the 4th woman to solo in state history. Dorothy, along with the other Rankin school pilots, frequently landed at Bernard’s Field in Beaverton (where McMenamins Cedar Hills Pub is now), which was a short hop from Rankin’s airport at Swan Island.

At ground school graduation, Tex Rankin (shown here with Dorothy at his right) urged the students to continue a career in aviation. He told the boys about the opportunities for flying the mail. As the only girl in the class, he told Dorothy she could work in the office. Dorothy vowed to make him eat his words. She found out that “Mr. Rankin,” as she called him all her life, would only fly with students by appointment. So, Dorothy made an appointment to fly with “Mr. Aviation.” Dorothy’s first flight with Tex began with basic maneuvers but ended with him showing her how to do an outside loop. When he told her she “flew like a boy,” Dorothy considered that the highest form of praise and she decided that life was not worth living if she couldn’t fly.

At 19, Dorothy was made a life member of the Women’s International Aeronautical Association and was given a silver bracelet by Lady Drummond-Hay, English aviatrix and the first woman to cross the Atlantic in a dirigible.

By 21, she was barnstorming and performing as a pilot with Tex Rankin’s Flying Circus, billed as “Princess Kick-a-Hole-in-the-Sky.” Dorothy’s flare for outside loops and snap rolls won her acclaim and reserved her a place in the aerobatic history books for generations. She barnstormed across the country, giving exhibitions in 38 states during a three-month period in 1931, and set several world records.

On May 15, 1931, Dorothy set a record of 56 inverted snap rolls, a record that has yet to be broken by any other man or woman. Two days later at an air show in Omaha, Nebraska, she established an unbelievable record of 69 consecutive outside loops (seven of which were not officially counted because they were judged not to be perfectly shaped.)

She opened her own flying school at the Rankin Airport in 1932, but grounded herself two years later to marry Robert D. Hofer. Though Dorothy put her career on hold to tend to her family, her flying days weren’t over. In 1948 (at age 38 and a mother of two), she became the first woman to take the U.S. Navy’s “G-test,” the forerunner to tests given to the first astronauts.

In 1980, Dorothy was inducted into the OX-5 Aviation Pioneers Hall of Fame, and was honored with a joint resolution by the 1985 Oregon Legislature, “for her courage, her determination and her achievements in aviation.” The Seattle Museum of Flight named her to its Pathfinder Hall of Fame in 1989 and in 2004, she was inducted into the World Aerobatic Club Hall of Fame.


  1. Beth Vandehey on August 15, 2019 at 7:16 am

    Wonderful story. Such great family history to know and share with my family. We had heard some of the story before but their were parts we didn’t know.

    • Kerry from McMenamins History on August 16, 2019 at 2:12 pm

      Thanks, Beth! We appreciate it — that piece was written by one of our assistant historians, Emlyn Stenger. Such a great story of a courageous woman!

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