On or about June 27, 1894, a twenty-three-year-old Jewish immigrant and mother of three named Annie “Londonderry” Kopchovsky pedaled away from Boston, Massachusetts, on a quest to become the first woman to bicycle around the world. Clad in a heavy Victorian corset and a full-length skirt, she carried nothing but a change of clothes and a pearl-handled revolver. She had taken up the challenge to settle a high-stakes wager between two wealthy Boston merchants who bet ten thousand dollars that no woman possessed the physical endurance or self-reliance to circle the globe on a bicycle. Annie’s journey was an absolute masterclass in late-nineteenth-century self-promotion. Lacking personal funds, she transformed her own body and her bicycle into a rolling billboard, renting out advertising space on her clothes and her frame to corporate sponsors. She legally changed her last name to “Londonderry” in exchange for a one-hundred-dollar sponsorship from the Londonderry Lithia Spring Water Company, perfectly capturing the spirit of the “New Woman” era and proving that women could successfully navigate the world entirely on their own terms.
The most captivating layer of Annie’s story is that she was an extraordinary fabricator who treated her trek as a grand theatrical performance, a trait that directly explains why historians still debate her exact departure date. While many modern timelines record her historic launch on June 27, local newspaper archives and family records suggest she actually rode out on June 25, a discrepancy that Annie herself likely encouraged or ignored to keep journalists chasing the story. She had only learned how to ride a bicycle a few days before setting out, and because her forty-two-pound Sterling wheel was far too heavy for mountainous terrain, she actually traveled large portions of her global route by steamship and train, counting the miles toward her total. When lecturing to packed auditoriums, she enthralled audiences with wild, entirely invented tales of hunting tigers in India, dodging bullets on French battlefields, and being thrown into a Japanese prison, proving that her genius lay not just in her legs, but in her brilliant, modern understanding of celebrity and media manipulation.
