10 books like On the Road

Herman Hesse’s Indian tale follows the ancient journey of Siddhartha, a fictional character on a spiritual path to find meaning in a world full of suffering and greed by renouncing his family and all worldly possessions to become a wandering holy man (Samana).

Along his journey he discovers and meets the actual Buddha (Gautama Buddha), and although he was deeply impressed with the Buddha’s honorable teachings, Siddhartha, disappointed, chose instead to follow his own path believing that one cannot find enlightenment by only following the words of a teacher but instead by experiencing and embracing all aspects of life personally to understand the true nature of enlightenment.

The story itself is captivating because the answers Siddhartha seeks are questions we’ve all asked ourselves, and the answers he discovers help explore the contradictions between the sacred texts of organized religion and the frustrated individual’s approach to find meaning within themselves despite… show more.

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.

This is the story of Steinbeck traveling around the country for three months in a truck camper with his dog Charlie. The aging writer set out to rediscover the real America that he had been writing about his whole career. In the process he not only gains a new understanding of the country but of himself. For me, it was fascinating looking at the United States through 1960 eyes and realizing that while much has changed, we still face many of the same issues they dealt with then. Like my own experiences it was also a wonderful reminder that we grow from taking on challenging adventures. 

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.

The oral historian and radioman Studs Turkel takes us around American without leaving his Chicago via Division Street America. Sparsely contextualized by his interstitial commentary, Turkel exercises his embracing interviewing skills to bring poignant stories of the non-celebrity class into sharp, relevant focus. This same type of unornamented approach earned a Nobel Prize in literature for Belarussian journalist Svetlana Alexievich and her Chernobyl.

And no such list is complete without Alexis de Tocqueville's classic from the 19th century, Democracy in America. Weighing in just two pages short of Don Quixote's 937 (paperback both, the ECCO Grossman Quixote translation and the Penguin Gerald Bevan de Tocqueville edition), Tocqueville ponders a question most of us contemplate and plenty of us act on: "Why Americans are so restless in the midst of their prosperity..."

Founding text of the modern fantasy genre, expander of Homer's beautiful or horrific fantastic gallery; but unlike Odysseus or Christian, Tolkien's characters change, either to grow or become "better," or to spectacularly regress. This novel-type flux matches his unique gift, the modulation of style. Most good writers can find one "voice" and maintain it. But unlike the films, the books will show you Tolkien starting in a cozy-children's-story mode in the Shire, rising to the King James Bible or mythic level of Gandalf's resurrection story, or the Fields of Cormallen – and then drawing the whole vast arc of quest and war down into Sam's circle to the Grey Havens, and the six concluding so-simple monosyllables: "'Well, I'm back," he said."

Being forged by nature doesn’t come more visceral than Strayed’s wilderness memoir. Her journey along the Pacific Crest Trail, as she sloughs off layer after layer of pain, regret, and disillusionment—along with skin and toenails—while fortifying herself with newly realized strength, comradery, endurance, and insight, is cathartic for the reader. Scenes where she processes the death of her mother… read only when you need a deep, purging, life-affirming cry. 

I’m afraid this one might have lost its luster after they turned it into a mediocre film. I think it is still worth all the hype it got when it came out! Elizabeth Gilbert has a warm, engaging writing style, and I love any writer (and person) who can be honest about the good, bad, and ugly of a human life. This is a wonderful story of self-exploration and the many paths available to grow our spiritual lives. 

All aspiring hikertrash have to start somewhere and Derick relates this journey with great honesty and humor. I started my vagabond life on the Appalachian Trail a decade before Derick did, but I found myself laughing in commiseration with his escapades as he learned what it means to walk across the country. Unlikely captures not only the highlights of hikertrash life, but also the lows, the drudgery, and the beautiful camaraderie that forms between people on journeys. Whether you hike or wander a different path, these themes connect for us all.