There was a time when a woman climbing aboard a motorcycle and setting off across America was considered scandalous. Crossing the country alone? Absolutely outrageous. And suggesting that women might be capable of serving their country as motorcycle dispatch riders? Well, that was simply beyond the imagination of some gentlemen in positions of authority.

Two wheel adventures and the women who dared to ride in the first decades of the 20th century. These are not just tales of road trip adventure. They are exciting and inspiring chapters in the American story. And they are great examples of the stories we like to share at Jim HInckley’s America.

The Van Buren sisters, Bessie Stringfield, and Effie Hotchkiss who was featured earlier in this series. These women weren’t just pioneers in petticoats. They were adventurers that faced challenges beyond muddy roads and lack of services.

Setting The Stage

In the early decades of the 20th century, a patchwork of muddy trails, rutted wagon roads, and gravel paths served as highways. These were where three remarkable women who wrote exciting chapters in the history of the great American road trip. They also pushed boundaries and provided inspiration for generations of women.

Augusta and Adeline Van Buren were two adventurous sisters who rode Indian motorcycles across the United States in 1916. Their adventures challenged conventional thinking about women and their place in society.

Then there was Bessie Stringfield, an African American motorcycling pioneer. She rode thousands upon thousands of miles through a country where racial prejudice could make even finding a place to sleep a dangerous undertaking.

Their stories are about courage, independence, determination, and the freedom of the open road. They are also tales of inspiration. And they are the sort of stories that remind us why the American road trip is about more than getting from one destination to another.

Augusta and Adeline Van Buren: 5,500 Miles and a Mission

While much of America was celebrating Independence Day on that hot summers day in 1916, two sisters were preparing for an adventure that would become one of the most remarkable motorcycle journeys in American history.

One year after Effie Hotchkiss and her mother became the first women to cross the country by motorcyle, Augusta Van Buren, and her younger sister Adeline, born in 1889, departed from Sheepshead Bay in Brooklyn, New York, on their Indian motorcycles. Their destination was California.

Unlike Hotchkiss’s adventures, these daring sisters took to the roade with a purpose. The sisters were active in the National Preparedness Movement and intended to show that women with training would be well suited to serve as military motorcycle dispatch riders. Their trip would erode the common misconception that women were not capable of handling the grueling demands of long-distance motorcycle travel.

After careful evaluation, they selected the latest Indian PowerPlus models for the trip. Equipped with gas headlights these durable machines were built for serious touring in rugged conditions.

An Epic Adventure

The sisters headed west on the Lincoln Highway. Even though this road was the first built specifically for coast to coast automobile travel, it was not a highway in the modern sense of the word. Much of it consisted of unimproved dirt roads, especially west of the Mississippi River.

Rain would turn the road into a quagmire. Ruts, rocks, mud, and mechanical troubles were daily challenges. There were no conveniently located roadside services, hotels with modern services were a rarity, and even restaurants could be a gamble.

If a motorcycle became stuck in the mud, or needed repair, the solution was to get off, get dirty, and figure out how to get moving again. The sisters also dealt with an issue not experienced by their male counterparts. Local law enforcement.

Pikes Peak

The sisters persevered. They crossed the Mississippi River and conquered the mud choked roads of the plains, and arrived in Colorado prepared to tackle the challenging terrain of the Rocky Mountains. It was in Colorado that the sisters accomplished something remarkable.

The Van Buren sisters became the first women to reach the summit of Pikes Peak on a motorized vehicle. The road was steep, winding, and dangerous, particularly for two women riding heavily loaded motorcycles. But they made it, and they made national headlines.

From Colorado, they continued their westward journey over difficult mountain roads and through punishing deserts all while fighting fatigue, hunger, and mechanical challenges. They endured spills, muddy roads where the bike had to be pushed, and incidents when assistance from local residents made the difference between life and death.

West of Salt Lake City the sisters became lost in the desert. They were without water and low on gas when, miraculously, a mule skinner hauling supplies to a remote mine happened upon them. Water and gasoline were a part of his cargo.

An Epic Adventure

The adventuresome sisters reached San Francisco on September 2, 1916. They continued down the coast to Los Angeles arriving on September 8. For good measure, they continued south to Tijuana, Mexico.

By the time they returned to New York, their adventure had covered more than 5,000 miles. They had accomplished something extraordinary.

Unfortunately, their efforts to convince the military that women were capable of serving as dispatch riders were unsuccessful. Adeline’s application was rejected.

But the sisters had made their point. Their accomplishment challenged conventional attitudes about women, transportation, and independence.

Adventures of Another Kind

Both women continued to pursue remarkable lives. Adeline eventually earned a law degree from New York University after teaching English. Augusta became a pilot and joined the Ninety-Nines, the organization of women pilots founded with the involvement of Amelia Earhart.

The Van Buren sisters were inducted into the American Motorcyclist Association Motorcycle Hall of Fame in 2002. There is an irony in this recognition.

After completing their epic adventure many newspapers, and even motorcycling magazines, framed their historic trip as a vacation. Some editorials framed the trip as an excuse for housewives to wear men’s clothing and escape domestic duties.

Bessie Stringfield: The Motorcycle Queen of Miami

If the Van Buren sisters demonstrated that women could conquer the challenges of the American road, Bessie Stringfield took that challenge into territory where the obstacles were even greater.

Born in 1911, Bessie became one of the most important African American pioneers in American motorcycling. During the 1930s and 1940s, she completed eight long-distance solo motorcycle journeys across the United States.

She did this in an era of Jm Crow laws and sundown towns when the The Negro Motorist Green Book was an alamost mandatory travel companion for African Americans. And there were still societal restrictions on women.

The challenges Stringfield faced didn’t end there. Much of America was struggling with the crushing economic consequences of the Great Depression. Roads were often still primitive. Motorcycles required near constant mechanical attention. Long-distance touring was an undertaking that required determination and resourcefulness.

With Boldness

With boldness Stringfield met every challenge head on including segregation and racial prejudice that made travel through portions of the country dangerous. Finding a restaurant or lodging that would serve her was a daily battle.

Boldly she traveled through the former Confederate states where racial discrimination presented genuine threats to her safety. Years later, while recounting her experiences, she described how she often relied on the hospitality of African American families when she needed a place to stay. When that wasn’t possible, she sometimes slept at filling stations or along the road.

Undaunted Bessie kept riding.

A Life Defined by Independence

Bessie’s adventures were not simply about accumulating miles. They were about living life on her own terms. She challenged assumptions about women, African Americans, and motorcycling at a time when all three could be subjects of considerable prejudice. In spite of these challenges she would ride through all 48 states.

The Van Buren sisters would have been proud. During World War II, she served as a civilian motorcycle courier for the United States Army. Following the war, she settled in Miami, Florida, where she founded the Iron Horse Motorcycle Club. Her accomplishments earned her the nickname The Motorcycle Queen of Miami.

She was inducted posthumously into the AMA Motorcycle Hall of Fame in 2002. The American Motorcyclist Association also established the Bessie Stringfield Award, recognizing individuals who help bring emerging markets and new participants into motorcycling.

Her story is an important chapter in African American history, women’s history, and the history of American motorcycling. It is an inspiring story. And it is an American story.

It is also a reminder that the early years of the great American road trip presented many challenges. The courage required to travel in these years required more than a mechanical aptitude. Bessie Stringfield understood that better than most.

The American Road Trip: More Than Miles and Motorcycles

There is a common thread connecting the Van Buren sisters and Bessie Stringfield. They each understood that the road represented opportunity with each challenge faced and overcome.

For the Van Buren sisters, it was an opportunity to challenge social conventions and demonstrate that women could accomplish things society considered beyond their capabilities. For Bessie Stringfield, it was an opportunity to live independently and pursue an adventurous life despite the restrictions imposed by racial prejudice.

Their stories also remind us of something easily overlooked when discussing the history of American transportation. The automobile and motorcycle revolution did more than change how people traveled. It changed how people thought about opportunity, independence, and the world beyond their hometown.

In the early 1900s, a coast-to-coast trip was a major undertaking. Today, we can cross the country on interstate highways in a few days, stopping at comfortable motels and enjoying restaurants along the way. But for the passionate road trip enthusiast, the spirit of adventure remains unchanged.

There are still people who understand that the best adventures often begin when we take a road less traveled.

Where History Meets the Highway

For those interested in exploring the history of American motorcycling and early road trips, there are wonderful opportunities to connect the stories with real places. The American Motorcyclist Association Motorcycle Hall of Fame in Pickerington, Ohio, preserves the stories of pioneers such as the Van Buren sisters and Bessie Stringfield.

The Lincoln Highway, the route followed by the Van Buren sisters for much of their journey, offers an opportunity to explore one of America’s earliest transcontinental highways. And in Colorado, Pikes Peak remains a landmark of American motoring history.

All across the country, museums, historic highways, and communities preserve pieces of these amazing stories. These are the kinds of places that help make a road trip memorable.

They encourage us to do more than simply drive through. When we stop, explore and talk with the locals we discover the real America.

Visit the museum. Find the old downtown business district. And if you happen to discover a little roadside diner serving exceptional pie, well, that’s just an added bonus. After all, a road trip without a little pie is like a motorcycle without wheels. Something important is missing.

Have a Cup of Coffee and Share the Adventure

Stories such as those of Augusta and Adeline Van Buren and Bessie Stringfield are wonderful examples of why I started sharing America’s story and inspiring road trips back in 1990. At Jim Hinckley’s America, we believe history should be more than a collection of dates, names, and dusty paragraphs in a textbook.

History should be fascinating. It should be relevant. It should make us think, encourage us to explore, and inspire us to discover the people and places that helped shape this remarkable country. And that brings us to Coffee With Jim.

Coffee With Jim is the weekly podcast from Jim Hinckley’s America on our YouTube channel. It is a virtual diner where we gather to share featuring fascinating guests and discussions about road trips, tourism, historic preservation, and community development. And it where we inspire a road trip or two.

On Podbean, Coffee With Jim features recorded, trivia-filled stories about America’s history, transportation, colorful characters, and adventures from the past. New episodes are published weekly. Sometimes we explore Route 66. Sometimes we talk about the early automobile industry. Sometimes we introduce you to an extraordinary individual whose name deserves to be remembered.

And occasionally we discover a story that makes you wonder how it could possibly have escaped your attention for so long. The adventures of the Van Buren sisters and Bessie Stringfield are precisely the sort of stories that make Coffee With Jim such an enjoyable journey.

The Jim Hinckley’s America Network

You can find us here:

• Coffee With Jim on Podbean: https://jimhinckley.podbean.com/
• Jim Hinckley’s America on YouTube: Visit the channel and explore the Coffee With Jim programs, historical features, road-trip videos, and conversations with fascinating guests.
• Jim Hinckley’s America website: https://jimhinckleysamerica.com/

Jim Hinckley’s America: It’s a Shared Adventure!

The story doesn’t end with a podcast or a blog post. Jim Hinckley’s America is a growing, multifaceted network built around a simple idea. That is the sharing of America’s story and inspiring road trips by telling people where to go.

Since 1990, the adventure has grown from magazine articles and books into a network encompassing the website, podcasts, YouTube, Substack, Facebook, Instagram, presentations, and community partnerships.

Our mission is to introduce you to fascinating people, remarkable places, historic highways, forgotten stories, and destinations that deserve a place on your road-trip itinerary. We want to make history relevant, fascinating, fun, and inspirational.But most importantly, we want you to become part of the adventure.

Here’s how you can join us:

• Follow or subscribe to Coffee With Jim on Podbean and enjoy weekly chapters from America’s amazing story.
• Subscribe to the Jim Hinckley’s America YouTube channel and join us for Coffee With Jim conversations, interviews, and road-trip adventures.
• Join a growing community of people passionate about road trips through Jim Hinckley’s America on Facebook and Instagram.
• Subscribe to Jim Hinckley’s America on Substack for additional stories, updates, and behind-the-scenes adventures.
• Visit jimhinckleysamerica.com regularly for new articles, road-trip inspiration, and fascinating discoveries.
• Share our articles and programs with friends who appreciate history, road trips, and the American story.

And don’t be shy about joining the conversation. Share your own road-trip stories, recommend a fascinating destination, or introduce us to someone with an extraordinary story to tell. We are always looking for another adventure.

Lessons Learned

The Van Buren sisters rode more than 5,000 miles to prove a point. Bessie Stringfield crossed America time and again despite obstacles that would have discouraged many others.

They understood something that remains true today. The road is full of possibilities for those willing to explore it.

So, pour another cup of coffee, find a fascinating stretch of highway, and start planning that next adventure.

Telling people where to go and sharing America’s story since 1990.

That’s what we do at Jim Hinckley’s America.

And remember, it’s a shared adventure!

Come along for the ride.

— Jim Hinckley