Telling the tall tale of Bessie

An inspirational young woman

I first came across the story of Bessie Stringfield during the month of February. Here in the United States, February is Black History Month, and a short video of her popped up on social media. The video told an abbreviated story of a young, Black woman who rode her motorcycle around the US at the age of eighteen, during the late 1920s. This was a time of segregation and Bessie defied that as she lived her life on the road on her motorbike. How did she determine where she was going? A flip of a penny. And that inspired me to tell her story.

The video ended and I wanted to know more. But there wasn’t much more. Online searches all yielded the same information, which came from the same person; a motorcycle-riding journalist that Bessie told her personal story to and shared in print. So, using the little bit of information that I had, I began working on telling Bessie’s story.

Anytime I do a biography on someone, I have to get the basic facts straight: where and when they were born and where they lived. At the early stages of writing, I relied on what Bessie had told the journalist. She was born in Jamaica and, around the age of five, was brought to America by ship with her mother and father. Unfortunately, her mother died on the crossing and her father abandoned her shortly after. She was then adopted by a white woman in Boston, Massachusetts. At least, that’s what Bessie said. I would later learn otherwise as time passed and more information about Bessie became known from other sources.

With so many details in question, I decided to focus on one detail that attracted me to Bessie’s story in the first place: her pennyflip adventures. The challenges of being a young, Black woman on a motorcycle during segregation were plenty, so I wanted to show what Bessie went through. I wanted to show how she earned money, found places to sleep and get gas, and mostly, the freedom with which she lived her life.

For me, Bessie was a reminder that freedom can’t be given to you, it’s there if you choose to take it. Because freedom means living your life as you choose, no matter the difficulty. Bessie’s story embodies that and will hopefully inspire others to do the same.

CHARLES R. SMITH JR., Author of Bessie the Motorcycle Queen www.charlesrsmithjr.com