The best books channeling the spirit of Jack Kerouac’s On the Road

Ah, the lure of the back roads, the unbeaten paths, the “blue highways”—to use the term popularized by William Least Heat-Moon in his stirring, soulful travel book of that name. From the first pages, I heard the song of the open road as I read, and the music didn’t stop until the last paragraph. Kerouac’s novel was published the year before I was born. Least Heat-Moon’s book appeared a quarter-century later, when I was a young man yearning to find myself on the open road. Blue Highways was cathartic: it showed me that a journey on America’s back roads—and a book about that journey—was still possible in an America that had changed significantly since Kerouac’s time.

Robert M. Pirsig’s Zen and the Art of Motorcycle Maintenance was first published when I was a teenager. I was aware of the book’s unforeseen popularity and countercultural reputation, but it proved too daunting for me at the time. I read it years later, after I had read Blue Highways, and was immediately enthralled with the road trip dimension of the book (Pirsig travels from Minneapolis to San Francisco on his motorcycle, accompanied by his son and some friends—not on the same motorcycle, of course). It’s a compelling journey across the austerely beautiful northern tier of the American West; it’s also a darker journey into the narrator’s troubled past. Much of the book is given to philosophical inquiry—an intellectual trip that’s just as compelling as the physical journey.

Jack London lived and died before Kerouac was born, so it’s more accurate to say that On the Road channels the spirit of London’s book, published some 50 years before Kerouac’s masterpiece. The Road is a compelling memoir about tramping across the United States at the end of the nineteenth century. London anticipates Kerouac’s bohemian spirit as he rides the rails with vagabonds, hoboes, and tramps (as London explains, there’s a difference among them). To my mind, The Road is an underappreciated American classic, poetically evoking that quintessential American characteristic, restlessness—the deep-seated desire to “follow the breeze.” Fifty years later, Kerouac stuck out his thumb and followed in London’s footsteps.

Perhaps no one—including Kerouac—embodies this characteristic restlessness more purely than Chris McCandless, the subject of Jon Krakauer’s Into the Wild. McCandless’s story has captured the imagination of legions of readers, myself included (not everyone is on board; there are those who consider McCandless a fool). I’m sure I’m not the only one who read the book in one sitting, unable to set it down. What’s so mesmerizing about McCandless’s story, for those who can’t resist it, is his utter belief (saintly in its way) that the physical journey is in fact a quest, a kind of soul-searching that leads to enlightenment. That his journey ends badly somehow seems to validate his belief. McCandless dared to go to the limits, even if it meant there was no return.

Curiosity about hobo life led Ted Conover to drop everything and ride the rails for a spell. What he learned became the basis of his first book, Rolling Nowhere. It’s filled with the things I love best about these books: fascinating characters, indelible scenes, and movement through landscapes both sublime and gritty. On every page, there’s a reminder of Kerouac and London. Reading it, I am filled with longing, the urge for going, wanderlust. I’m older now; I’ve done my share of traveling and written about it, too. But maybe I’m not totally done with it: a half-mile from my comfortable house, my street intersects with the road out of town, the city limits sign visible in the distance. And beyond: desert, wide sky, open road. A boundless dreamland.