Londonderry was born in Latvia to Annie Cohen Kopchovsky and emigrated to the United States as a kid. Londonderry utilized her alias to reinvent herself as a globetrotting biker and saleswoman when she was 24 years old. Londonderry challenged two wealthy Boston men who had wagered tens of thousands of dollars that no woman could cycle across the world in just 15 months. Historians now believe Londonderry made up the story to increase interest in her voyage and attract businesses to sponsor her by purchasing advertising space on her bicycle.Londonderry set off on her voyage in 1894 with nothing except a bicycle, a pearl-handled revolver, and a change of clothes–including bloomers, the contentious garment that allowed women to move more freely. Despite injuries and difficulties along the way, she made it to the end of her journey with 14 days to spare. Londonderry was able to traverse the world and visit faraway destinations such as Alexandria, Saigon, Hong Kong, and Kobe by sailing from country to country when necessary. For a woman and mother at the time, this was no easy task. Londonderry's journeys demonstrated to her contemporaries that women can be self-sufficient, athletic, and businesswomen.