Why do some improve over time while others fade? What makes us follow or strike off on our own? Over the course of seven years, Moor traveled the globe, exploring trails of all kinds, from the miniscule to the massive. He learned the tricks of master trail-builders, hunted down long-lost Cherokee trails, and traced the origins of our road networks and the Internet. In each chapter, Moor interweaves his adventures with findings from science, history, philosophy, and nature writing. Throughout, Moor reveals how this single topic—the oft-overlooked trail—sheds new light on a wealth of age-old questions: How does order emerge out of chaos? How did animals first crawl forth from the seas and spread across continents? How has humanity’s relationship with nature and technology shaped world around us? And, ultimately, how does each of us pick a path through life? Moor has the essayist’s gift for making new connections, the adventurer’s love for paths untaken, and the philosopher’s knack for asking big questions.