Outside Lies Magic by John R. Stilgoe (Walker, $15). What John Berger’s Ways of Seeing did for traditional oil painting, this book does for roads and landscapes: It helps you to understand what you’re looking at, from the layout of towns to the placement of electric lines to the distance between street and dwelling. It’s a reminder that, even in a young country like the United States, we live in the past. And it’s an argument for going outside and opening your eyes.

On the Road by Jack Kerouac (Penguin, $8). Kerouac wrote this novel in the same year that The Catcher in the Rye was published, and some of the language feels as dated. But there is no purer expression in American culture of the energy and glory of road travel, of the possibility of transcendence through movement.

In Patagonia by Bruce Chatwin (Penguin, $15). There’s a reason he didn’t call it In Argentina: Chatwin was after mythos. In this quiet celebration of language and the oddness of a backwater settled by people from all over, he achieves the evocative power of great fiction.

The Road by Cormac McCarthy (Vintage, $15). The sober flipside of Kerouac, a dystopian view of roads as last resort, a place to look for food and shelter in the nuclear winter. McCarthy’s roads, stripped of civic purpose, are conduits of danger, the setting for the final acts of the human drama. Epic and riveting.

The Conquest of New Spain by Bernal Díaz del Castillo (Penguin, $16). A conquistador who accompanied Hernán Cortés on his march from the Gulf of Mexico to Tenochtitlán describes the “new world” when it was new—and truly astonishing. Neither the newness nor the Aztec Empire would last for long: As the Romans learned, the same roads that help to make an empire grow can bring it to its knees.

The Places in Between by Rory Stewart (Houghton Mifflin, $15). An argument for audacity (Stewart walked across Afghanistan eight years ago, while war was raging), combined with education (he speaks Dari), and the wit to ignore received opinion about our “enemies” (he’ll talk to anybody).