Mary Shepard Cutright

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Mary: The Trailblazer of Two Wheels

Mary’s love affair with motorcycles began in her youth, sparked by the thrill of riding a push bike her brother bought from a local Harley dealer. By age 15, she had already claimed victory in her first bicycle race, igniting a passion that would define her life. Upon graduating high school, she secured a job at a shoe factory, with one clear goal in mind: to buy her first motorcycle. Her determination paid off when she purchased a brand new 1937 45 cubic inch Harley-Davidson, eager to learn the ropes from the local boys who were all too willing to teach her the art of riding.

Navigating Challenges

The excitement of riding was tempered during the war years, when gasoline shortages made long rides impossible. Mary made do, commuting to work on her 1940 61 cubic inch Harley. But the constraints of marriage and motherhood would never keep this intrepid woman from the open road. Mary continued to ride throughout her pregnancy, and just eight weeks after giving birth to her son John in 1944, she was back in the saddle. With John nestled in front of her, she rode the highways and byways until he grew tall enough that he could no longer see over her handlebars, at which point she moved him to the back.

In her early riding days, Mary primarily rode with men, but occasionally spotted another woman on a motorcycle. It was through these encounters that she learned about the Motor Maids, a prestigious women’s motorcycle organization. In 1949, Mary eagerly signed up, launching a decades-long journey filled with friendship and adventure.

Leadership and Legacy

Mary’s enthusiasm for the Motor Maids was quickly recognized; she was appointed State Director for Southern Ohio in 1952. Her remarkable leadership skills earned her the role of Supply Officer in 1957, followed by Treasurer in 1963. In 1966, at the convention in Sturgis, South Dakota, she made history by being elected as President of the Motor Maids, a position she held for an impressive twelve years.

Her commitment to the Motor Maids was unwavering; she never missed a convention. For Mary, these gatherings were more than just meetings; they were cherished reunions where old friendships were rekindled and new connections were made. The conventions were filled with exciting activities, from navigating dirt roads to visiting gold mines, to conquering the summit of Pikes Peak. Mary, standing at just 5'1", tackled each challenge with determination, collecting hundreds of trophies along the way as proof of her skill and grit.

Adventurous Journeys

As a seasoned rider who traveled across the country, Mary amassed a wealth of stories from her adventures. In 1959, she and her son John embarked on a cross-country journey to the convention in Santa Ana, California, navigating through Reno, Sacramento, and Yosemite. At the convention, the Motor Maids participated in the opening parade lap at Ascot Speedway. On their return journey, Mary’s friend Grace experienced a breakdown, but with her characteristic resourcefulness, Mary secured a rope and towed Grace’s BMW behind her Harley, showcasing her preparedness and riding prowess.

Another memorable adventure occurred in 1962 while en route to the convention in Seattle, Washington. During the ride, Mary and her husband became separated from John, who was riding with a friend’s husband. John, captivated by the stunning scenery in Yosemite, stopped for a photo op without realizing his parents had taken a different route. With no cell phones or walkie-talkies available, it took the group three long days to reunite at Yosemite’s western exit.

A Life Celebrated

In 1987, Mary was diagnosed with cancer, which prevented her from attending the convention that year. She bravely fought the illness but tragically passed away in 1988, leaving behind a legacy that family and friends continue to celebrate. Mary’s contributions to the sport she loved and the memories she created on her motorcycle endure, inspiring future generations of riders.

Mary’s story is not just about a woman on two wheels; it is a tribute to a pioneer who broke barriers, fostered friendships, and embraced life to the fullest. Her spirit remains alive in the hearts of all those who share her passion for the open road, reminding us that the journey is just as important as the destination.