I first heard about this story on Futility Closet's blog here, and then did some research on my own.
"The Gilded Age certainly saw some high-stakes wagers. Twelve years before Harry Bensley settled one bet by pushing a pram around the world, Annie 'Londonderry' Kopchovsky settled another by circling the earth on a bicycle.
"Annie’s task, proposed by two wealthy Boston clubmen, was to ride around the world in 15 months, earning $5,000 en route. She saw it as a challenge to make her way in a man’s world, and in 1895 the doughty 23-year-old, who had never ridden a bicycle before, pedaled out of Boston, leaving behind a husband and three children.
"She brought only a change of clothes and a pearl-handled revolver, but she steadily earned money by carrying advertising banners and ribbons through cities around the world, starting with the Londonderry Lithia Spring Water Company, which paid her to carry its placard on her bike and to adopt her nickname.
"That spirit carried her through. On returning home, the victorious Annie wrote a series of sensational features for the New York World, beginning with her cycling adventure. 'I am a journalist and ‘a new woman,' she wrote, 'if that term means that I believe I can do anything that any man can do.'"
What's remarkable was not only that she biked around the world in 15 months, never having been on a bicycle before, and managed to turn a $5,000 profit in doing so, but that it actually took way less than 15 months: she biked halfway across America (from Boston to Chicago), before ultimately changing her mind (probably due to the harsh midwest winter), biking all the way back to her starting point, and going around the world the other way.
Her journey was as follows:
She biked from Boston to New York, New York to Chicago, from Chicago back to New York, and then took a boat over to Le Havre, France. She biked from Paris to Marseilles (a trip of almost 500 miles) in only two weeks. After that, she grabbed a boat from France to Egypt and biked around Egypt, Jerusalem, and Yemen, before sailing to Colombo and Singapore. Eventually she sailed back to San Francisco, biking through LA, El Paso, and Denver, drawing huge crowds and telling tales about her journey. She made her way cross country and reached Boston 15 months after she had left.
While she didn't, strictly speaking, 'bike' around the world, but more circumnavigated the globe with and sometimes on a bike, she still managed to drum up international fame and financial support, and more than proved that a woman was capable of fending for herself in a wide variety of situations. To many, she is the embodiment of the New Woman, who not only rode a bike and wore bloomers instead of dresses, but also valued her own freedom and agency over, or at least equal to, domesticity. What's more, she insisted on having her own voice, and wrote many pieces about her travels.