Say the name Bessie Stringfield in a room full of riders, and chances are excellent that you'll get one of two reactions. Some won't know her name, simply because no one knows everything, and you don't know what you don't know until you learn.

But those who do know her name will also likely know at least some of her lifetime of trailblazing accomplishments. At the very least, they'll probably know her enduring nickname, the Motorcycle Queen of Miami.

In one version of her story, Stringfield was born in Jamaica in 1911, to parents who moved to Boston a short time later. They unfortunately died of smallpox when she was five, so Stringfield was soon adopted and raised by her new parents. Those same parents reportedly gave her a 1928 Indian Scout 101 for her 16th birthday, thus helping to fuel what would become a lifelong passion. 

Another version of her story was later told to the New York Times by Stringfield's niece, Esther Bennett. She said that her aunt's parents had come from North Carolina, and that she didn't know anything about an adoption.

Either way, though, the fact that Stringfield found her way to motorcycling and used her life spent on two wheels to change the world is indisputable.

Bessie and Arthur Stringfield

As the motorcycle part of the story goes, once she completed high school, Stringfield went on to complete eight cross-country journeys across America by motorcycle. She was a Black woman in a world that was harsh and unkind to Black people (let alone women), but she refused to let it stop her.

Along the way, she earned money at carnivals, county fairs, flat track events, and hill climbs. She also served as a dispatch rider during WWII. The surname Stringfield apparently came from her third husband, and it stuck. Although she died in 1993, the legend of Bessie Stringfield still inspires those who hear it, even decades after her death.

Why Don't More People Know About Bessie Stringfield?

Even learning the broad strokes of Stringfield's story, you'd think that it would be ripe for major motion picture and documentary treatment. Amazingly, though, that hasn't really happened until now.

To Myself, With Love: The Bessie Stringfield Story is a new documentary film from director Diane Weis. It's set to premiere at the 13th annual AmDocs American Documentary and Animation Film Festival in Palm Springs, California from March 21 through 25, 2024. 

Over the past four years, Weis and her small but dedicated team have been working to assemble the first-ever Bessie Stringfield documentary. Together with the members of the Bessie Stringfield All-Female Ride, who were integral to the film, putting the story together has been an honor, a labor of love, and an effort whose time has come.

We had the chance to ask director Diane Weis and Bessie Stringfield All-Female Ride founder Tameka Singleton some questions about the project ahead of the film's premiere in March. 

This interview has been lightly edited for clarity.

To Myself, With Love The Bessie Stringfield Story Poster

Can you please tell us how you first learned about Bessie Stringfield and her story?

Tameka:  I learned about Bessie Stringfield through a brief conversation with a former club brother. He suggested to start a ride in her name. After researching her, I decided this amazing woman definitely needed to be honored so I started to organize a ride in her name. The Bessie Stringfield All-Female Ride went eight years marking her eight trips across the country.

Diane: Bessie lived in Opa-Locka, Florida from the 1950s until she passed in 1993. I grew up in Miami and in the 1980s when I was working at a local TV station, I heard about her and her extraordinary achievements.

Bessie Stringfield Documentary - Tameka Singleton

Tameka Singleton, Bessie Stringfield All-Female Ride co-founder

What inspired you to start putting a documentary about her life and her enduring influence together?

Diane: It was 2019 and I had just had a successful run at film festivals with an animated short and was thinking about my next project. Bessie’s story had stayed with me through the years.

I began to research and discovered that there had never been a film produced about her. I was rather stunned. Bessie was a courageous, daring trailblazer. Riding a motorcycle across the U.S in 1930 during the Jim Crow era, alone, at the age of 19! And that is just one of her many barrier-busting feats.

At first, I was planning to produce a short animated film because there is not much available online or in archives about her. Then, when we started planning to film the Bessie Stringfield All Female Ride’s 8th and final event of hundreds of women riding from Daytona to Key West, I began to see this was going to be a very different type of project than I originally thought.

I reached out to my friend, entertainment attorney Ned McLeod, and to producers Kim Dawson, Beth Hubbard, and Gabby Revilla Lugo to join the production. From there, we kept going and found sources, material and information that had never been made public. Four years of non-stop research. We knew this needed to be shared to tell Bessie’s authentic story and honor her.

Bessie Stringfield Documentary - Editing

How did you two meet and begin to work together on the documentary?

Diane: One of the first calls in my research was to Harley-Davidson, because Bessie owned 27 of their bikes during her life. I spoke with the head of archives, Kimberly Thomas, who herself has a strong interest in Bessie and has been supportive of the film. I asked her if she could recommend any people and/or motorcyclists that might know about Bessie. She recommended I reach out to Tameka.

My first call, actually a Zoom meeting with Tameka and Lynn Wigfall, the historian for the All-Female Ride, was kind of a launching point for the direction of the project. The way they spoke about Bessie and how inspired they were by her and her achievements and how they encourage other female riders to ride long distance like Bessie, really moved me. I knew then that these women and the Ride needed to be a part of the film to show Bessie’s impact today 30 years after her passing.

Tameka: Diane reached out and we began to chat about her intentions for a documentary. The issue on my end was that we were preparing for the last Ride which had a lot of logistics organizing hundreds of female riders to travel from Daytona to Key West. But we immediately figured out how to work with the production crew to best capture the last Ride for use in the film.

Bessie Stringfield All Female Ride

What's the most surprising and/or interesting thing you learned while researching Stringfield's life?

Tameka: The most surprising and interesting thing I learned about Bessie was that she was the Founder/President of her motorcycle club, the Iron Horse Motorcycle Club in Opa-Locka, Florida in 1965 which consisted of all male members. During that time, to have a female in charge of men was unheard of and truly to this date and time, it is still unheard of. She is an extraordinary lady in that way.

Diane: You will have to watch the film because the most surprising thing I learned has
never been made public before and I don’t want to be a spoiler.

Having said that, all the people that we found that knew Bessie, from the executor of her estate to a riding friend of hers, the way everyone spoke about her with such high regard and affection. It wasn’t as much surprising as it was so wonderful to hear how much of an impact she had on people.

Bessie Stringfield All Female Ride - Group

How did the Bessie Stringfield All-Female Ride begin?

Tameka: It began after I researched Bessie Stringfield and joined with 5 other women who shared a sisterhood of riding long distance, Original 6: Tameka “Kurvez” Singleton, Lashonda “Mi$$Fit” Oglesby, Infini “Shai” Hardy, Brenda “Babs” Young, Niecy “Bobble” Fambro, and Shannon “Red" Lewis.

You've said that the documentary premieres at AmDocs in Palm Springs in March 2024. Do you have plans for additional screenings in the future that you can share with us?

Diane: We are very excited to be an Official Selection at AmDocs. We have submitted to film fests across the country and internationally and should be hearing soon about selections. We will post updates on our Facebook page. [Find the link in our Sources if you want to follow the project for updates.]

Are there any plans you can tell us about in the works for a DVD or streaming release of the film down the line?

Diane: We hope to get distribution and also develop a narrative feature about Bessie. There is so much more information and material we have about her that is not in the documentary that could be included in a feature.

I would just like to add how grateful I am for everyone that has been involved in this project all with the goal to share Bessie’s remarkable story with the world.

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