The late Bessie Stringfield, whose motorcycle escapades gained her the title of “Motorcycle Queen of Miami,” is the subject of a new display at the Harley-Davidson Museum in Milwaukee featuring her personal effects—some which have never before been seen publicly.
The exhibit was announced in September, on the heels of a the award-winning 2024 documentary short exploring her life, “To Myself With Love: The Bessie Stringfield Story.”
“It was an honor to bring Bessie’s remarkable journey to the screen,” said director Diane Weis, who sees the new Harley Museum display as a continuation of the film’s work to highlight the legendary Black biker.
“This exhibit is a powerful extension of that work—an opportunity for audiences to see firsthand the life and legacy of a woman who not only rode against the wind but changed history.”
Now open! The first-ever exhibit of Bessie Stringfield’s personal possessions at the Harley- Davidson Museum in Milwaukee. #motorcycle #Travel #BessieStringfield #Wisconsin #Milwaukee #news pic.twitter.com/Wky9wVUE8b
— Diane (@wordzgirl) September 25, 2025
Stringfield’s lifelong struggle against racism included rewriting her early life, including her birth in 1911 and early upbringing in North Carolina. She was reportedly adopted by an Irish-American woman in Boston at the age of five and became a Catholic under her influence. It is known that she began riding motorcycles in her teen years, later taking on professional work as a carnival stunt rider and civilian courier during World War II.
As part of her work—and leisure—Stringfield made several cross-country trips on her own Harley-Davidson motorcycles, facing opposition due to her race and her status as a woman in a male-dominated biker culture.
She has noted that she always leaned on her faith, keeping Rosary beads and statuettes of Jesus and Mary on hand during her rides. She even spent time in a convent discerning religious life before returning to the open road.
“I was always out there by myself,” Stringfield said in an interview with filmmaker Alice Stone in the 1990s. “[But] I had the man upstairs. He never leads me wrong.”
The new exhibit in Milwaukee features items courtesy of Laugh More Entertainment, which produced the 2024 documentary in Stringfield. They include vintage photographs, awards, and even biking gear she wore during her extensive travels.
“Bessie Stringfield’s story is one of courage, resilience, and the sheer joy of the open road,” said Ann Sinfield, curator of the Harley-Davidson Museum.
"We are honored to bring her personal items into the public eye for the first time, ensuring her contributions to motorcycling are recognized and celebrated.”
Stringfield became a fixture of the Florida motorcycle scene in her later years, gaining the trust and admiration of local bikers as well as the larger community, and continued to ride even into her 80s. She also worked as a nurse and founded the Iron Horse Motorcycle Club.
She died of a heart condition in 1993 and is the namesake of several biker honors, including the Bessie Stringfield Memorial Award from the American Motorcyclist Association, founded in 1990. She was posthumously inducted into the AMA’s Motorcycle Hall of Fame in 2002.
Nate Tinner-Williams is co-founder and editor of Black Catholic Messenger.
