Bessie Stringfield: A Legendary Harley-Davidson Owner

By Derek Shiekhi - February 14, 2017

‘Motorcycle Queen’ Rode Her Harley Across the U.S. in Dangerous Times

As we celebrate Black History Month, we raise a toast to one particularly bold and badass Harley rider who broke the rules, popped a few pistons and made history. Her name is Bessie Stringfield, a Jamaican-American woman who was recently profiled in Timeline. The fearless adventurer’s story is an inspiring one of traveling over the rough, dirt roads of a pre-interstate-highway America to deliver messages for the U.S. Army. And she did it all in the name of helping her fellow Americans during one of the country’s most turbulent times.

Also, Bessie’s selfless service allowed her to engage in her favorite past time: riding Harley-Davidson motorcycles. During World War II, Stringfield used her Harley to travel through the racially-charged South of the 1930s and 1940s on her way across the country, carrying messages between domestic Army bases.

She loved Harley-Davidison motorcycles so much that she owned 27 of them over the course of her 82-year life. Stringfield once said Harley-Davidsons were “the only motorcycle ever made.” Clearly, motorcycles were the only way she preferred to travel. According to the American Motorcyclists Association Hall of Fame: “At 19, she began tossing a penny over a map and riding to wherever it landed. Bessie covered the 48 lower states. Using her natural skills and can-do attitude, she did hill-climbing and trick-riding in carnival stunt shows.” When Stringfield encountered hotels who refused to admit her because of the color of her skin, she would ride to a filling station, lay her jacket across her bike’s handlebars to use it as a pillow, then put her feet up on the rear fender. That resourcefulness helped her complete a total of eight cross-country trips in the U.S. in the 1930s and 1940s.

‘I’m very happy on two wheels,’ Stringfield says in Hear Me Roar.

Stringfield also helped the Army during World War II as a civilian motorcycle dispatch rider — on the back of her blue Harley-Davidson. In the ’50s, she moved to Miami, where she worked as a registered nurse and founded the Iron Horse Motorcycle Club. To prove to the local police department that she, as a black woman, had a right to ride a motorcycle, she showed the chief of police her skills. He must have been impressed because Timeline states the cops never hassled Stringfield again.

Crowds were impressed by her racing, too. Stringfield became known as the “Motorcycle Queen of Miami.” In 2000, seven years after her death, Stringfield’s life and career inspired the American Motorcycle Association to name its annual prize for “an individual who has been instrumental in bringing emerging markets into the world of motorcycling” the AMA Bessie Stringfield Award.

The roads she traveled were not easy ones, in physical or social terms, but she was always somewhere that made her smile, even if that was only on the inside. When being interviewed by author Ann Ferrar for her 1996 book Hear Me Roar: Women, Motorcycles and the Rapture of the Road, Stringfield says, “I’m very happy on two wheels.”