Although many people might not have heard of her, Bessie B. Stringfield is a Black female pioneer in the world of motorcycling. Born in the island nation of Jamaica in 1911, Bessie immigrated to Boston with her parents at a very young age. Before turning 5, she became an orphan after both of her parents died of smallpox. She was then adopted by an Irish woman who gave Bessie pretty much whatever her heart desired. For some undisclosed reason, Bessie would never publicly mention the name of her adoptive mother. Bessie grew up being spoiled and on a whimp, she asked her adopted mom for a motorcycle for her 16th birthday.
So on her birthday, she received a new 1928 Indian Scout motorcycle. When she got her new wheels, Bessie had no clue of how to operate a motorcycle and had to teach herself how to ride. She quickly got the hang of it and became very skilled at riding. In 1930, at just 19-years-old, Bessie set off on her first ride across America. At a time when practically no woman would even dare to get on a motorcycle, Bessie blazed a trail for herself and other women to follow. In total, she made eight trips across America; passing through all the continuous 48 states. She would also ride across various parts of Europe, Brazil, and Haiti.
Through the years, Bessie supported herself by performing motorcycle stunts at carnivals around the country. She proved herself as a formidable rider by becoming a civilian dispatch courier for the US Army during World War II. She spent 4-years working for the government and being responsible for delivering documents between American military bases. Being comfortable only on Harley-Davidson motorcycles, Bessie rode her own blue Harley as she worked for the Army. As a Black woman and a motorcycle rider, Bessie faced many instances of racism while traveling across the country. At one point, a white male in a pickup truck ran her off the road as she rode her motorcycle in the South. On another occasion, a white police officer in the Miami suburb where she lived told her, “nigger women are not allowed to ride motorcycles.” After being repeatedly pulled over, Bessie went to the police captain and lodged a complaint. At a local park, she showed the captain her riding abilities and wasn’t harassed by the cops anymore.
At a time of severe segregation, attempting to ride cross country would be a dangerous endeavor for any Black person, especially a Black woman. Bessie explained how she was able to complete her journeys this way, “If you had Black skin, you couldn’t get a place to stay. 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 Stringfield lead a unique and intriguing life. She was married and divorced a total of six times. After three unsuccessful pregnancies with her first husband, she ultimately remained childless. In addition to her work as the only female courier in her Army unit, Bessie also became a licensed practical nurse and founded the Iron Horse Motorcycle Club. She was originally known as the “The Negro Motorcycle Queen” but that was later changed to “Motorcycle Queen of Miami” with her move to south Florida. In recognition of her outstanding ability as a motorcyclist, the American Motorcyclist Association (AMA) inducted her into their Motorcycle Hall of Fame in 2002. The AMA created the “Bessie Stringfield Memorial Award” in 2000, to honor the exceptional achievements by a female motorcyclist.