David Lamb’s Over the Hills: A Midlife Escape Across America by Bicycle (1996) is one of the better examples of the mid-life-crisis-bike-trip travel book that started to pop up in the 1980s and 90s and has become a subgenre all its own.
Lamb was the same age I am now (54) when he found himself not in a crisis exactly, but feeling “tiresomely reliable and responsible,” “normal to a fault,” he says. He hadn’t ridden a bike more than a few miles in decades, but he decided that a “foolhardy” cycling adventure from Virginia to California might just be the ticket to reconnecting with some of his roguish youth and getting out of a rut.