Meet the First Woman to Cycle Around the World (in 1895)

But not everyone. Women weren’t supposed to take on such crazy undertakings and adventures, never mind abandon their family for over a year. There was at least as much disapproval as approval and her own brother didn’t come to say goodbye, although he and her husband were in the crowd.

Support did come, though. The bicycle manufacturer, Londonderry, asked her to place an advert on the back of her bicycle for them and use their name as her surname for the trip. She happily obliged and made the first step towards completing the financial part of the wager. They paid her $100. As the trip progressed, she made money by advertising – pinning brands to herself and sticking signs to her bicycle.

It seems that Annie got the hang of cycling pretty quickly. She headed towards San Francisco, but snow and bad weather left her stranded in Chicago by September. She wasn’t going fast enough. Something had to change.

She swapped her bike for a lighter model with one gear and no brake. She swapped her dress and corset for bloomers and eventually for male cycling attire. She also spotted a loop-hole in the rules. There was no stipulation about minimum distance cycled. In November she boarded a steam-ship to France and promptly had her bike confiscated by French customs. Against the odds, she continued to travel from place to place by boat, train and bicycle arriving back in Boston exactly 15 months after she left.