Bessie Stringfield: The Black Woman Who Rode Through Jim Crow America

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In the 1930s a young Black woman rode a Harley-Davidson alone across America, through towns where she couldn't get a room for the night and along roads where some people would happily have seen her dead. She did it eight times.

Bessie Stringfield went on to carry Army dispatches during the Second World War, race men in disguise, ride the Wall of Death and become the Motorcycle Queen of Miami. Yet more than 30 years after her death, nobody's completely sure where she was even born.

Quick Answers

Who was Bessie Stringfield? An American motorcyclist, usually credited as the first Black woman to ride solo across the United States and through all 48 lower states.
When was she born? In 1911. Where she was born is another matter entirely.
How many motorcycles did she own? 27 Harley-Davidsons and one Indian over her lifetime.
What did she do in WWII? She worked as a civilian motorcycle dispatch rider for the US Army.
When did she die? In 1993, aged 82, from complications of an enlarged heart.

The Story Bessie Told

The version Bessie gave for most of her life went like this. She was born Betsy Leonora Ellis in Jamaica in 1911, brought to Boston as a little girl and orphaned by the age of five. A wealthy Irish woman then adopted her, renamed her Bessie and raised her Catholic. The adoptive mother's name never came up in a single interview.

Even that version wobbles depending on who you ask. Atlas Obscura's account of her life sets out at least three different stories about her parents. In one, her mother was a domestic worker called Maria Ellis and her father was the mother's employer, and both died of smallpox soon after arriving in America. A 1981 Miami Herald interview had her mother dying in childbirth. Her friend and biographer Ann Ferrar, who interviewed her over several years, was told her father was a mixed-race West Indian man who took her to New England and then abandoned her.

Was Bessie Stringfield Really From Jamaica?

This is where things get murky. More recent research suggests the Jamaica story may have been something Bessie built for herself. A 2023 Boston Globe piece by Nate Tinner-Williams says her birth parents were actually a Black couple living in North Carolina, and her exact ancestry is still unclear.

Why would she reinvent herself? Nobody knows for certain. Ferrar has said Bessie didn't stick rigidly to the Caribbean origin story in private. One theory is that a foreign backstory gave her a bit of armour in a country that treated Black Americans brutally. Another is that she simply wanted to keep her real past to herself. Either way, she pulled it off. She's still keeping people guessing three decades after her death.

A Teenager on an Indian Scout

Bessie caught the motorcycle bug young. She taught herself to ride on an upstairs neighbour's bike, and her adoptive mother, who wasn't keen on the idea, eventually gave in and handed her a motorcycle for her 16th birthday. It was a 1928 Indian Scout, and she'd never had any proper lessons.

Bessie always credited God with teaching her, and her faith rode with her for the rest of her life. She packed rosary beads and little statues of Jesus and Mary on her trips, and she even spent time in a convent weighing up whether to become a nun before the road pulled her back. Asked about her luck in the 1990s, she told an interviewer, "I had the man upstairs. He never leads me wrong." That line comes from the Black Catholic Messenger's coverage of her life.

She soon switched brands. Over the years she owned 27 Harley-Davidsons and just the one Indian, and she made her loyalties crystal clear to the National Motorcycle Museum crowd and anyone else who'd listen: "To me, a Harley is the only motorcycle ever made."

The Penny on the Map

At 19, Bessie came up with the travel method that made her name. She'd spread out a map of the United States, flip a penny onto it and ride to wherever it landed. Through the 1930s and 1940s she made eight long-distance solo rides across the country and eventually covered all 48 of the lower states. She's also said to have ridden in Brazil, Haiti and parts of Europe.

It's worth remembering what roads were like back then. Even a well-equipped party driving through Death Valley in 1926 treated the trip like an expedition. Bessie did it on two wheels, on her own, again and again.

How Bessie Became the First Black Woman to Ride Across America

A woman on a motorcycle in the 1930s was unusual enough. A Black woman riding alone through the Deep South was genuinely dangerous. Hotels and motels routinely turned Black travellers away, so Bessie slept wherever she could. She'd find a Black family willing to put her up or, failing that, she'd sleep on her bike at a filling station. She summed it up bluntly in an interview quoted by the American Motorcyclist Association: "If you had black skin you couldn't get a place to stay."

It wasn't just the lack of beds. On one trip a white man in a pickup truck followed her and then forced her off the road, knocking her clean off her motorcycle. Bessie, typically, shrugged it off as one of the ups and downs of life on the road. A generation later, James Zwerg and the Freedom Riders would be beaten bloody for travelling through the same part of the country.

Wall of Death Stunts and Racing in Disguise

Bessie wasn't only a long-distance rider. She performed at fairs and carnival sideshows, including on the Wall of Death, a wooden drum where riders tear around the vertical walls, and inside spherical cages where bikes loop the loop. She did hill climbs and trick riding too.

Then there was flat track racing. Women weren't welcome, so Bessie sometimes raced on dirt ovals disguised as a man. When it came out that a woman had beaten the lot of them, the organisers often refused to hand over the prize money. On one occasion she won, took off her helmet and watched the cash disappear on the spot.

Bessie Stringfield in World War II

When America entered the Second World War, Bessie put her skills to work for the Army as a civilian motorcycle dispatch rider. She was the only woman in her unit, carrying documents between bases inside the US on a blue Harley bearing a military crest.

The training was no joke. Among other things she learned to build a bridge out of rope and branches for crossing swamps, though she never needed it on duty. Like the female war photographer history nearly forgot, her wartime work barely got a mention for decades.

Six Husbands and Three Lost Children

Bessie's private life was every bit as eventful as her riding. She married six times and every one of those marriages ended in divorce. She taught two of her husbands to ride. The surname she's remembered by came from husband number three, who asked her to keep it after they split.

There was real heartbreak too. She lost three children, and none survived into adulthood. In later years her dogs often rode along with her on the bike instead.

How She Became the Motorcycle Queen of Miami

Bessie eventually settled for good in Miami, bought a house there and qualified as a nurse. In 1981, at the age of 70, she was still nursing and still riding, church trips included.

Miami's police didn't make it easy at first. Officers gave her a hard time for riding at all and wouldn't give her a licence. So she went to the captain of the motorcycle police and showed him what she could do. After watching her ride figure eights and pull off her tricks, he gave her the licence.

She also founded the Iron Horse Motorcycle Club, which has long since gone, and the local press started calling her the Motorcycle Queen of Miami. Close friends just called her BB.

Riding Until the End

In her later years Bessie developed an enlarged heart and her doctor told her to stop riding. She refused, telling him that if she didn't ride she wouldn't live long. She kept going and died in 1993, aged 82, in Opa-locka, Florida. She'd asked for no services, though a funeral Mass was eventually held for her at St Martha Catholic Church in Miami Shores. She left no known family behind.

Bessie Stringfield's Legacy

Most of the recognition came after she'd gone. She was honoured at the opening of the Motorcycle Heritage Museum in Ohio in 1990, and in 2000 the American Motorcyclist Association created the Bessie Stringfield Award. It's handed out every year to someone who's helped bring new groups of riders into motorcycling. Two years later she was inducted into the AMA Motorcycle Hall of Fame.

Since then she's turned up in children's graphic novels and as a fictionalised character in HBO's Lovecraft Country in 2020. The Bessie Stringfield All Female Ride ran in her honour from 2014 to 2021.

In 2024 a short documentary, To Myself, With Love: The Bessie Stringfield Story, directed by Diane Fredel-Weis, did the festival rounds and was put forward as an Oscar contender for best documentary short. In September 2025 the Harley-Davidson Museum in Milwaukee opened a display of her belongings, including photos, awards and riding gear, some of which had never been seen in public before.

Bessie was a pioneer in the same mould as Bessie Coleman, America's first Black woman pilot, someone who flatly refused to accept where she'd been told she belonged. She may well have invented parts of her own backstory. But the bit that really matters, a Black woman riding a Harley alone through Jim Crow America and coming home every time, is no myth.