Bessie Stringfield

Bessie Stringfield was born in Jamaica and raised in Boston after being orphaned young. She received her first motorcycle at sixteen and taught herself to ride, later claiming she chose her cross-country routes by throwing a penny at a map — wherever it landed, she rode.

Beginning in 1930, Stringfield became the first Black woman to ride a motorcycle solo across the continental United States, a journey she would go on to repeat eight times over the following decades, often riding through the Jim Crow South where she was frequently denied hotel accommodation because of her race and forced to sleep on her motorcycle at gas stations.

During the Second World War, Stringfield served as one of the only women in the US military's motorcycle despatch courier corps, carrying documents between domestic military bases on her own machine — a role of genuine danger and responsibility rarely offered to Black women at the time.

After the war, Stringfield settled in Miami, where she continued performing motorcycle stunts and founded the Iron Horse Motorcycle Club. In 2002, nearly a decade after her death, the American Motorcyclist Association created the Bessie Stringfield Award in her honour, recognising women who have made a positive impact through motorcycling.