He talks about those St Valentines Day Massacre Map-road-rallies that you see advertised in Games Magazine. They're like gimmick rallies... but instead of driving around the country, you're peering at a map. These map rallies have a devoted core of fans but are so tough that new folks have a hard time getting started. (Sound familiar?)
He talks with roadgeeks, who travel around documenting highways and their signage. And the occasional anecdote where someone will improve a highway's signage without asking permission first.
Alex Trebek makes a cameo. So do some folks who work on Google Maps: Jennings seems a bit breathless when talking about them; he says that folks at a geography bee thought of Brian McClendon as a "sex symbol". I'm not sure that's right. But I certainly could imagine Jennings thought of some of the Google maps folks that way.
If you're into maps, geography, wayfinding, or just reading someone funny write about stuff, you might like this book.