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  • Writer's pictureN.J. Mastro

Annie Londonderry: Con Artist or Master of Inventing One's Self?

I love to travel. Unfortunately, the coronavirus pandemic has put opportunities to roam the globe on hold for a lot of us over the past couple of years. My husband and I are not quite comfortable tripping abroad just yet. I was fortunate, however, to spend two months this summer on a solo journey that took me from my adopted state of South Carolina to my beloved home state of Minnesota to visit family and friends.

The open road is liberating. My spirit in high gear, my mind wanders. Oldies on Sirius Radio trigger memories that turn into mental side trips. When I tire of music, podcasts give me something to noodle on that would otherwise escape notice. Landmarks offer yet another distraction. They call to me like sirens, begging me to stop and explore. Mark Twain’s Hannibal. Abraham Lincoln’s birthplace. Frank Lloyd Wright’s brilliant legacies in Chicago and Wisconsin. All fascinating, to be sure, but why was it on this trek through the Midwest I passed no points of interest that celebrated famous women? I failed to see a single one. I know there are memorable females; history just seems to overlook them.

Take women travelers, for example. It was easy for me to fill the tank of my SUV in the morning, drive by a fast-food window at lunch, and check in to a comfy hotel at the end of the day. But I couldn’t help wondering, what must it have been like for women travelers when modern conveniences weren’t so modern and conveniences not so convenient? What kind of women dared face the unknown, often with little to sustain them other than sheer will and determination? It got me thinking. Who were the first women to travel using transportation we take for granted in the twenty-first century?

This list of women is long, of course, and distinguished. And their modes of transportation vary. Take the humble bicycle.

Mabel Love, circa 1919

According to the National Women’s History Museum, a virtual museum dedicated to telling the story of women who transformed America, in 1895, suffragist leader Elizabeth Cady Stanton said, “the bicycle will inspire women with more courage, self-respect, self-reliance.”[1] Her friend and colleague, the iconic Susan B. Anthony, agreed and went a step further regarding the bicycle, which was also called “the wheel” at the time. Said Anthony: “I think it has done more to emancipate women than anything else in the world. It gives women a feeling of freedom and self-reliance. I stand and rejoice every time I see a woman ride by on a wheel…the picture of free, untrammeled womanhood.”[2]

“I think it [the bicycle] has done more to emancipate women than anything else in the world. It gives women a feeling of freedom and self-reliance. I stand and rejoice every time I see a woman ride by on a wheel…the picture of free, untrammeled womanhood.”

If women like Stanton and Anthony viewed the bicycle as a fundamental asset on the road to emancipation, one can only imagine what the average woman must have thought of the bicycle.

Consider one Annie Cohen Kopchovsky, a.k.a. Annie Londonderry.

The Facts

In the early 1890s, the United States was shifting to an industrial economy, changing the way Americans lived and worked. For the first time in our nation’s history, factories employed more people than farms. Times were good financially, and as so often happens when money is flowing, investors gave in to the temptation to over expand. In time, several key companies collapsed. Banks failed, prompting bankruptcies like the flick of one domino that sends the rest falling. Unemployment levels eventually reached over eighteen percent. By 1893, a depression so severe that historians call it the Other Great Depression, stalled a nation.[3]

In 1894, Annie Cohen Kopchovsky was one of those average women struggling to put food on the table. Her husband, a peddler who sold goods from a pushcart, didn’t earn enough to support his family. To help make ends meet, besides raising her three small children, Annie worked three days a week selling advertisements for several Boston newspapers. As we all know, it was atypical for a woman to work outside the home, even more unusual to be selling ads. Newspapers were a man’s world.

Sitting around one day, a group of businessmen in Boston wagered a bet: did a woman have the physical stamina to cycle around the world? A man had already done so, but could the fairer sex? Our obscure Annie Kopchovsky had no doubt a woman could and stepped up to prove it. Pick me, she said. I can do it! Her work selling ads had placed her in a unique position to put her hat in the running. With some finagling, she was finally selected. According to the bet, if successful, Annie would earn $10,000. She must, however, conclude her trip in fifteen months. And she must earn $5,000 along the way. You can find details of the legendary wager here.

So why would a bunch of men bet on a woman riding a bike around the world? To sell bicycles, of course. Annie’s trip was a scheme to market the wheel to half of America. Bicycles were a still a relatively recent phenomenon. Men had been cycling for the two decades since the French invention of the bicycle as we think of it today, which was called a velocipede[4]. (A German invented the very first bicycle in 1818.[5]) American women, however, were just beginning to ride. Originally, those with means had access, but the contraption was catching on fast. By this time, there was even a female stunt team.

Kaufman’s Cycling Beauties stunt team, circa 1890

Now the funny part was, Annie Kopchovsky had never ridden a bicycle. Never mind, she said. She’d seen it done. She would learn. You have to admire the woman’s can-do spirit. As for raising $5,000 on her trip? No problem. Annie knew how to close a deal. She’d been selling newspaper ads during a depression. I’m your girl, she insisted. More points for Annie’s chutzpah. I imagine her being very convincing.

On the first day of her trip, she accepted an offer of $100 if she’d place an advertisement on her bike for the Londonderry Lithia Spring Water Company. For this compensation, she also agreed to be known during her trip as Annie Londonderry. Of course, this achievement on her first day didn’t happen by accident. She planned it in advance. Annie, we come to find out as we delve into her story, was a master at public relations. In June 1894, she peeled away from the steps of the Boston Statehouse on a new Columbia bicycle. In a dress. Packing a revolver.

Annie Londonderry

Annie accomplished her feat in the prescribed fifteen months and returned to Boston victorious. Afterward she resumed her life as Annie Kopchovsky and moved to the Bronx where Joseph Pulitzer’s newspaper, The World, hired her to write. She would assume yet another pseudonym for her articles: Nellie Bly, Jr. But as luck would have it, after reuniting with her husband, Annie became pregnant. These things happen. Her brief stint as a reporter ended.

Today, Annie is revered in the bicycle world and by people like me who admire daring women. Numerous articles have been written about her. You can find a good number of them at a website hosted by her great-grandnephew Peter Zheutlin, including several articles penned by him.

The Fiction

Spin: A Novel Based on a (Mostly) True Story is Peter Zheutlin’s fictional account of Annie’s celebrated journey. Spin is told in first person point of view in the form of a long letter Annie writes to her granddaughter, Mary. With Annie’s voice to guide us, we experience her story from before the start of her journey all the way to the finish line. The novel has all the adventures one would expect and includes colorful characters to boot. I felt like I was riding along with Annie. It was easy to fall under the spell of her good-natured narrative and sharp wit, as testified in the passage below:

“It was considered unladylike for a woman to be seen in public exerting herself on a bicycle, or, God forbid, exposing her ankles in the process. The moralists, often backed up by the testimony of medical men, argued that riding a bicycle, which brought a woman’s private parts—oh, let’s call them what they are, you’re a grown woman now—genitals in contact with the saddle, would be sexually stimulating to women, and lead to all kinds of moral decay … You’d have thought that women on bicycles was the end of femininity and a harbinger of the decline of Western civilization itself! Such folly.”[6]

I won’t try to summarize the novel or the many articles about Annie in this short post. I want you to read about her for yourself. She is a fascinating woman. The facts alone about her epic undertaking are incredible.

If you can call them facts.

Spin is an apt title for the novel by Zheutlin, who found while researching his ancestor that Annie tended to embellish her exploits. She did, in fact, circle the globe on a bike. But the truth behind her story is rather nuanced. Did she really pedal her way around the world? Not quite. Were all the outrageous stories of her encounters along the way true? Not so much. What does appear to be true is that she was inventing herself mile by mile.

Annie’s unusual story raised a ton of questions for me. First, why would she assume a challenge like cycling the globe when she didn’t know the first thing about riding a bike? Was she delirious? Overconfident? Self-absorbed? Or was she audacious and just plain ambitious? Second, what skills and abilities did Annie possess that enabled her to succeed in such a daring mission alone across foreign lands? And third, was Annie a pathological liar?

At first, I felt put off when I found out Annie appears to have fabricated parts of her story. She’d conned me; she seemed too dishonest. But the more I investigated Annie, the less the facts regarding her journey mattered and the more I wanted to know what made Annie tick.

Annie "Londonderry" Cohen Kopchovsky

We know that Annie was willing to mask her identity, and we can guess why. Her surname Cohen Kopchovsky was simply too Jewish. Given the discrimination Jews faced worldwide, as the face of a marketing campaign, her name was a potential liability. Sadly, her name may have also been a threat to her safety as well. Second, the promulgators of the bet didn’t want the public to know she was a married woman leaving behind three children under the age of five. The optics of it didn’t mesh with the businessmen’s marketing goals. It would produce a scandal and sink the whole venture. (I doubt had she been a man there would have been any concern about her children being left behind. No one ever seemed to question Earnest Shackleton who spent years exploring the Antarctic. But there you have it.)

According to Zheutlin, Annie also suffered from melancholia. By some accounts, Annie was discontented. If we believe Spin, she didn’t particularly take to motherhood. Women like Susan B. Anthony stirring the pot around women’s suffrage fascinated her. Nellie Bly, who had just traveled the globe to see if Jules Verne’s popular book Around the World in 80 Days was possible, mesmerized her. I’ve no doubt Annie loved her children. But Annie didn’t appear to be cut out for the beaten path. The suffrage movement seems to have stoked an apparent restlessness regarding the limitations of her gender. Maybe, she thought, things could be different for women. Zheutlin also leads us to suspect Annie was a lesbian or bisexual. Denied economic and educational choices, the norms of the day also denied her sexual freedom.

As I discovered these things about Annie, her story started to make more sense to me. Annie, it would seem, may have already been living a lie not being able to be her authentic self. No wonder stretching the truth came naturally to her. What was one more fabrication? No wonder she seized the opportunity to assume a new identity, even if only for fifteen short months. Annie’s cage door opened, and she bolted.

Annie’s unusual story reminds me of the fairy tale of “The Handmade Red Shoes” as told by Dr. Clarissa Pinkola Estés in Women Who Run With the Wolves. In this classic, many centuries-old tale of the red shoes, a young girl is on a journey to find her consciousness and assert her own power in the world. The red shoes represent mobility and freedom.[7] In Estés’ superb analysis of “The Handmade Red Shoes,” she includes an excerpt from the poem The Red Shoes by Anne Sexton:

I stand in the ring

In the dead city

And tie on the red shoes…

They are not mine.

They are my mother’s.

Her mother’s before.

Handed down like an heirloom

But hidden like shameful letters.

The house and the street where they belong

Are hidden and all the women, too,

Are hidden…[8]

I see Annie everywhere in the tale of “The Handmade Red Shoes” and in the excerpt from Sexton’s poem. While I don’t condone fabricating the truth—we see far too much of that these days—I became less critical of her when I began to understand how desperately unhappy she must have been.

In Women Who Run With the Wolves, Estés said this: “When a woman pretends to press her life down into a nice tidy little package, all she accomplishes is spring-loading all her vital energy down into shadow. ‘Fine, I’m fine,’ such a woman says. We look at her across the room or in the mirror. We know she is not fine. Then one day, we hear she has taken up with a piccolo player and has run off to Tippicanoe to be a pool hall queen. And we wonder what happened, because we know she hates piccolo players and always wanted to live on Orcas Island, not on Tippicanoe, and she never before mentioned anything about pool halls.”[9]

Annie seems like one of those women ready to head off to Tippicanoe. You may know some women who've gone there too. Figuratively speaking, when the opportunity to wheel around the world presented itself, Annie probably said to hell with it and kicked off her shoes, snatching the once in a lifetime chance to claim her independence before it disappeared.

Annie died in 1947 after becoming a successful businesswoman. But not before changing her name one last time to Annie Kay. She was inventing herself to the last.

Many criticized Annie for leaving her children and husband for those fifteen months, as her sponsors had feared. Had Annie’s journey taken place in America today, she’d no doubt have fared better in the public eye. The world has changed since then. She wouldn’t have to circle the globe to find purpose. She wouldn’t have to sneak a life. She’d have so many more choices growing up. She wouldn’t be forced to marry. She’d be free to love another woman.

Today, Americans view the bicycle more as a form of recreation than as a primary source of transportation, the exception being the hearty souls who ride their bikes to and from work every day or for city dwellers who’ve ditched the car entirely and can be found on any given day in the bike lane. In fact, I hear their numbers are growing. In developing nations, however, the bicycle means to women the same thing it did over one hundred years ago to Annie Kopchovsky, Cady B. Stanton, and Susan B. Anthony.[10] To women in developing nations, a bicycle is enabling an important freedom, a means to asserting their independence. Because of the bicycle, they too will change perceptions regarding women in their cultures, and in doing so, change the world.

"Another day riding." Africa, Photo credits: François Marsh, 2015.

For more information on Annie “Londonderry” Cohen Kopchovsky, I urge you to explore the articles at the end of this post. They include wonderful photos of Annie that due to copyright restrictions I am not able to share here. And definitely read Spin: A Novel Based on a (Mostly) True Story by Peter Zheutlin. I am grateful to Zheutlin for bringing Annie’s story to modern readers. Spin is fast a ride. It will remind you just how much opportunities for women have evolved in a century.

I can’t help but wonder, if she was alive today, what would Annie think of flying in a spaceship to the moon? Would she be trying to contact Jeff Bezos or Sir Richard Branson, begging them to take her along? As for me, I’ll stick to more conventional modes of transportation. Though I did take my bicycle with me during my summer sojourn. I enjoyed putting on a few miles on another open road: the bike trail. More nourishment for my own untrammeled womanhood.

Thanks for reading. I’m glad you’re here.

N.J. (Nancy) Mastro


[1] National Women’s History Museum, retrieved from

[2] Ibid.

[3] John S. Gordon, “The Other Great Depression,” American Heritage, May/June 1991.Retrieved from

[4] Joukowsky Institute for Archaeology & the Ancient World. Brown University, retrieved from

[5] Ibid.

[6] Zeuhtelin, P. (2021). Spin: A Novel Based on a (Mostly True Story). Pegasus Books: New York.

[7] Estés, C.P.E. (1992). Women Who Run With the Wolves. Ballantine Books: New York.

[8] Ibid. p. 243-44

[9] Ibid. p. 237

[10] National Women’s History Museum. Retrieved from


“Annie Londonderry,” West End Museum, retrieved from

“First woman to cycle the globe begins journey,” Jewish Women Archive, retrieved from -

“Overlooked No More: Annie Londonderry, Who Traveled the World by Bicycle,” The New York Times, retrieved from

“Annie Londonderry Biked Around the World: 1895.” Racing Nellie Bly, retrieved from


Daryl Byklum
Daryl Byklum
Sep 05, 2021

Loved this post. Even got Minnesota into the introduction. These are the stories that too often end up in the dustbin of history. Well written.

Sep 07, 2021
Replying to

Thanks for reading and commenting, Daryl! I love hearing from readers. Annie's story is one of many that I hope to tell on these pages. We can only imagine what propelled her across the globe on a bicycle, It is fun to think of what it might have been like to be alongside her.

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