"Bessie Stringfield’s life is the stuff of which legends are made. Bessie has been mentioned in books, magazines, newspapers and television documentaries. In 1990, when the American Motorcyclist Association opened its Motorcycle Heritage Museum, Bessie featured in its inaugural exhibit on Women in Motorcycling. A decade later the AMA created the Bessie Stringfield Award to honor women who are leaders in motorcycling. In 2002, she was inducted into the Motorcycle Hall of Fame. Bessie, or BB as she was known among friends, described over 60 years of motorcycling: “I was somethin’! What I did was fun and I loved it.”
In the 1930s and 1940s Bessie made eight long-distance, solo rides across the United States. Speaking to a reporter, she dismissed the idea that “nice girls didn’t ride motorcycles in those days.” She was also seemingly fearless about riding through the Deep South when racial prejudice was a tangible threat.
Born in Kingston, Jamaica, in 1911, she was brought to Boston as a young child but was orphaned by the age of 5. “An Irish lady raised me,” she recalled. “I’m not allowed to use her name. She gave me whatever I wanted. When I was in high school I wanted a motorcycle. And even though good girls didn’t ride motorcycles, I got one.” She was 16 when she climbed aboard her first motorbike, a 1928 Indian Scout, and, despite having no prior knowledge of how to operate it whatsoever, Bessie proved to be a natural. She insisted God gave her the skills. ”My [Irish] mother said if I wanted anything I had to ask Our Lord Jesus Christ, and so I did,” she said. “He taught me and He’s with me at all times, even now. When I get on the motorcycle I put the Man Upstairs on the front. I’m very happy on two wheels.” She was especially happy on Milwaukee iron. Her one Indian notwithstanding, Bessie said of the 27 Harleys she owned in her lifetime, “To me, a Harley is the only motorcycle ever made.”
At the age of 19 Bessie Stringfield began tossing a penny onto a map and then riding to wherever it landed. She covered all of the 48 lower states. Bessie’s faith got her through many nights. ”If you had black skin you couldn’t get a place to stay,” she said. “I knew the Lord would take care of me and He did. If I found black folks, I’d stay with them. If not, I’d sleep at filling stations on my motorcycle.” Bessie folded her jacket on the handlebars as a pillow and rested her feet on the rear mudguard. Using her skills and can-do attitude, she also performed trick riding in carnival stunt shows.
Between her travels, Bessie wed and divorced six times, declaring, “If you kissed, you got married.” She and her first husband were deeply saddened by the loss of three babies and Bessie had no more children. On divorcing her third husband, Arthur Stringfield, she said, “He asked me to keep his name because I’d made it famous!”
During the Second World War, Bessie worked for the army as a civilian motorcycle dispatch rider. The only woman in her unit, she completed rigorous training maneuvers. She learned how to weave a makeshift bridge from rope and tree limbs to cross swamps, although she never had to do so in the line of duty. With a military crest on the front of her own blue Harley, a “61,” she carried documents between domestic U.S. bases. Bessie encountered racial prejudice on the road. On one occasion she was followed by a man in a pickup truck who ran her off the road, knocking her off her bike. She played down her courage in coping with such incidents. “I had my ups and downs,” she shrugged.
In the 1950s, Bessie bought a house in Miami, Florida. She became a licensed practical nurse and founded the Iron Horse Motorcycle Club. Disguised as a man, Bessie won a flat track race but was denied the prize money after she took off her helmet. Her other antics, such as riding while standing in the saddle of her Harley, attracted the attention of the local press. Reporters nicknamed her the “Negro Motorcycle Queen” and later the “Motorcycle Queen of Miami.”
Late in life, Bessie suffered from symptoms caused by an enlarged heart. “Years ago the doctor wanted to stop me from riding,” she recalled. “I told him if I don’t ride, I won’t live long. And so I never did quit.” Before she died in 1993, at the age of 82, Bessie said, “They tell me my heart is three times the size it’s supposed to be.” An apt metaphor for this unconventional woman whose heart and spirited determination have touched so many lives.