Mr. Hoopdriver is a frustrated draper's assistant in Putney, London. He is badly paid, over-worked, and he needs a holiday. He also owns a bicycle-though he is an awkward rider.

When his annual ten days' holiday comes around, Mr. Hoopdriver sets out on a bicycling tour of the “Southern Coast.” Will this adventure be enough to shake up the dreariness of his ordinary life? Will his escapist flights of fancy end in disaster? And what should he make of the constant reappearance of the “Young Lady in Grey”?

Wells wrote this story at the height of the bicycling craze and before the automobile. The bicycle gave freedom to the working class, weakened the English class structure and gave a boost to female emancipation. In his story he explores these changes.