Bessie Stringfield is one of the legends of women motorcyclist. Born in Kingston, Jamaica in 1911, she was brought to Boston as a young child but became an orphan by the time she was 5 years old. “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 climbed on her first motorcycle, a 1928 Indian Scount, at age 16. Having no prior motorcycle riding experience, 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 age 19 Bessie began tossing a penny on a map and then riding wherever it landed. In just a few years she had covered all the lower 48 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 sk
ills and can-do attitude, she also performed trick riding in carnival stunt shows.
During World War II Bessie worked for the Army as a civilian motorcycle dispatch rider. The only women in her unit, she completed rigorous training maneuvers. With a military crest on the front of her own blue “61” Harley, 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 1950's Bessie moved to Miami, Florida 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.