[6] Max, a devout Orthodox Jew, attended synagogue and studied the Torah, while Annie sold advertising space for several daily Boston newspapers.
Under the pseudonym Paul Jones, he started bicycling in mid-February 1894 claiming to be attempting a trip around the world in one year on a $5,000 wager.
Annie Londonderry's great-grand nephew and author of the authoritative history of her journey, Peter Zheutlin, has stated that "It's virtually certain, for example, that she concocted the wager story to sensationalize her trip".
[11] Annie Kopchovsky was a highly unlikely choice for the completion of this wager, starting with her name, which identified her as a Jew in a city and country where anti-Semitism was widespread.
Prior to leaving Chicago to ride home to Boston, she met with Sterling Cycle Works, whose offices and factory were located on Carroll Avenue.
[6] With the change in dress and bicycle, Londonderry was determined to complete her world trip, even though she only had eleven months to make it back to Chicago.
She followed her route back to New York City, and on November 24, 1894, she boarded the French liner La Touraine, destined for Le Havre on France's north coast.
Despite being held up by bad weather, she arrived in two weeks by cycling and train[2] with one foot bandaged and propped up on her handlebars[6] due to an injury on the road.
Riders could follow service roads made of hard packed dirt and stop at shelters for train crews, where they could get a meal and a bath.
[3] Near Gladbrook, Iowa, she broke her wrist when she crashed into a group of pigs and was forced to wear a cast for the remainder of her trip.
When she published an account of her exploits in the New York World on October 20, 1895, the newspaper headline described it as "the Most Extraordinary Journey Ever Undertaken by a Woman".
[6] Despite criticism that she traveled more "with" a bicycle than on one, she proved a formidable cyclist at impromptu local races en route across America.
Londonderry was a brilliant saleswoman and an exceptional storyteller, raising all of the money and attracting the media attention necessary for her trip to be a success.
Her main income was from selling advertising space on her bike and person,[2] hanging ribbons and signs for products ranging from bicycle tires to perfume.
[2] While in the United States, she told stories about hunting tigers in India with German royalty and getting sent to a Japanese prison with a bullet wound.
[18] In the 1920s, the business was burned and, Kopchovsky used the insurance money to start Grace Strap & Novelty in Manhattan, "with a man named Feldman she met at a Horn & Hardart restaurant.
[19][20] In 2013, Gillian Klempner Willman of Spokeswoman Productions wrote, directed and produced a 26-minute documentary film titled The New Woman - Annie "Londonderry" Kopchovsky.
[23] In August 2022, RIDE, a new musical based on Annie Londonderry's cycle by Freya Catrin Smith and Jack Williams, starring Liv Andrusier and Yuki Sutton, debuted at the Charing Cross Theatre.