Bessie Stringfield, the first Black woman to ride a motorcycle solo across the United States, was born in Kingston, Jamaica, in 1911 to a Jamaican father and a Dutch mother. While questions have arisen about her birth and family, the popular consensus is that the family moved to Boston, Massachusetts, and when she was five, her parents died. She was then adopted in Boston by an Irish woman. Stringfield taught herself to ride a 1928 Indian Scout motorcycle, her first, when she was 16, and at age 19, she began traveling across the United States, making sever long-distance trips and eventually riding through the lower 48 states, Europe, Brazil, and Haiti. She supported herself by performing motorcycle stunts in carnivals. She was challenged by the fact that she was often unable to find accommodations during her travels due to her skin color and ended up sleeping on the motorcycle at filling stations, and because she was a woman, she was refused prizes she won in the flat-track races she entered.

Stringfield worked as a civilian courier for the US Army during World War II, one of its few civilian motorcycle dispatch riders, and carried documents between Army bases in the US after completing rigorous training. She rode her own motorcycle, a blue Harley-Davidson, on these missions for four years, crossing the US eight times. She regularly experienced racism during these trips and once reported being deliberately run down by a white man in a pickup truck in the South. She moved to Miami, Florida, in the 1950s where police told her that Black women were not allowed to ride motorcycles. She contacted a police captain, who took her to a park to assess her riding ability, and she gained his approval and had no more trouble with the local police afterward. Stringfield qualified as a nurse in Miami and also founded the Iron Horse Motorcycle Club, receiving the nickname of “The Motorcycle Queen of Miami.” Stringfield was married and divorced six times during her life but retained the last name of her third husband. She continued to ride until her death in 1993. The American Motorcyclist Association (AMA) honored her in 1990 in their first “Heroes of Harley Davidson” exhibition, as she had owned 27 Harleys during her lifetime. The AMA created the Bessie Stringfield Memorial Award in 2000 to recognize achievements by female motorcyclists, and Stringfield was inducted into the Motorcycle Hall of Fame in 2002 for her achievement in breaking down barriers for women and Jamaican-American motorcyclists.