Hidden History on Two Wheels: The Story of Bessie Stringfield

The details of Bessie Stringfield's upbringing are shrouded in mystery. Pretty much the only consistency is that she was born Betsy Ellis. Some accounts say she was born in Jamaica in 1911, while others say she was born in America after her parents immigrated.

What's not clear is whether she was — or wasn't — of mixed race. Was she orphaned by the death of her mother and later abandoned by her father and then adopted by a wealthy Irish woman in Boston? Or did both parents die of smallpox?

The answers to some of those questions came when The New York Times published her 2018 obituary (25 years posthumously). In it her niece, Esther Bennett, goes as far as to imply the only thing white about her was her father's last name, and that both her parents were Black American and lived in Edenton, North Carolina. Bennett also states Stringfield was never adopted.

Stringfield's backstory might depend on where you land online, but Ann Ferrar, journalist and author of "African American Queen of the Road" met Stringfield in 1990 at the American Motorcycle Association's (AMA) Motorcycle Heritage Museum. Stringfield was 79 years old and part of the inaugural exhibit "Women in Motorcycling" and Ferrar was then a newly minted biker.

The two women became friends and Stringfield asked Ferrar to write her biography. Ferrar recorded numerous conversations with Stringfield during her final three years so she could help others recognize Bessie's achievements.

In an email interview, Ferrar says she supports the idea that Stringfield was mixed race, and that Stringfield lived as a Black woman thanks to her dark complexion and the "one-drop rule" — an archaic rule in the South that meant if you had "one drop of Black blood" you were Black. And Ferrar notes on her website that Stringfield was "born into a modest home in the Southeastern region of America in 1911."

Frankly, the muddled childhood details don't matter to the heart of Stringfield's story and do nothing to diminish her accomplishments as a pioneer in the intersecting worlds of motorcycling, Black history and women's history.

Bessie Stringfield received her first motorcycle from her mother at age 16 — a 1928 Indian Scout — although she didn't yet know how to ride. ("God taught her how to ride in a dream," Ferrar says.)

Now, for those of you who don't ride bikes, let me put this into perspective. A 1928 Indian Scout weighed probably more than 700 pounds (317.5 kilograms) in Stringfield's day — and she was barely 5 feet 5 inches (1.6 meters) tall. I'm above average height and pretty fit, but even I find handling that big motorcycle no simple task.

But in 1930, at age 19, Stringfield took off on that Indian Scout on her first solo gypsy tour — a ride without any route or destination planned. She tossed a coin over a map and rode to the location where it landed.

And she did this without the benefit of paved roads and today's interstate highway systems. Nor did she have roadside service if something broke down. She had to be both rider and mechanic. My teeth clench just thinking of navigating on gravel, loose sand or otherwise inhospitable roads and my towing service card is the only tool I have readily at hand.

Not to mention she began her years of gypsy touring in the '30s when women just didn't ride motorcycles, crisscrossing the pre-civil rights, Jim Crow South. Ferrar says Stringfield faced discrimination along the way, and was turned away from motels and was forced to sleep on her bike instead (not easy or comfortable, trust me). She was threatened, too, and one time was intentionally run off the road by a white male in a pickup truck.

Yet through it all, Stringfield didn't let those things stop her, or define who she should be. Societal norms were of no consequence to her. "Bessie's superpower was her ability to not focus on struggle, but rather in how she reacted to each situation and each individual," Ferrar says. "Bessie was too modest to see herself as [particularly special]."

That first ride at age 19 was only the beginning of her two-wheeled independence. Between the 1930s and her death in 1993, Stringfield wound up riding solo across the United States in eight separate trips, the first woman to ever do so. She supported herself by performing motorcycle stunts at fairs, including the Wall of Death where motorcyclists ride fast around the enclosed wooden vertical walls of a barrel-shaped arena.

Stringfield also competed in flat-track races, riding over oval dirt tracks. One story recounts how she was denied prize money after removing her helmet and revealing she was a woman.

She even used her riding talents in service to her country, a country that was still segregated even in the ranks in which she served. As a civilian courier in the early 1940s, she carried mail and documents between bases for the U.S. Army during World War II. She was the only female in the all-Black unit.

By the 1950s, Stringfield settled in Miami where she became a licensed practical nurse and founded the Iron Horse Motorcycle Club. She was known around town for riding her bike to work and church. But, according to a feature in the June 1996 issue of American Motorcyclist Magazine, she was initially given a hard time by local police.

And after being told "****er women are not allowed to ride motorcycles in Miami" she eventually went to see the captain. He gave her a series of "tricks" and figure eights to do. Amazed at her riding ability, he remarked he'd never seen a woman ride like that. She got her license and the harassment stopped. She eventually became known as the "Motorcycle Queen of Miami."

During her six decades of riding, Stringfield owned 27 Harley Davidson motorcycles and rode more than a million miles — gypsy style — hitting all 48 of the continental United States, plus motorcycle trips in Brazil, Europe and Haiti, according to Ferrar.

While Stringfield may not appear to have had a direct influence on the civil rights movement, she unknowingly did her part, empowering those who would come later. "Bessie made an impression on people in her community who were proud of her and always pleased to see this independent Black woman on a Harley riding around town," Ferrar says.

In 2000, the AMA began giving the Bessie Stringfield Award to women who are leaders in motorcycling. And in 2002, Bessie was inducted posthumously into the Motorcycle Hall of Fame.

She was a rule-breaker, an icon, an adventurer. A free spirit who managed to live life on her own terms. I never gave much consideration to the fact that had it not been for the bravery and boldness of someone like Stringfield, I might not be able to zip around relatively unscathed on America's highways as a woman. Learning her story has made an indelible impression on me and I don't think I'll ever be able to sit astride my Harley again without thinking of all she gave me and countless other women — of any race — who enjoy riding with knees in the wind.