Even as a 38-year-old guy, I still love the feeling of embarking on road trips. They promise freedom, romance, and adventure without the increasing arduousness of flying. All you need is a full tank of gas, a map (a paper one still has value!), and a willingness to explore unexpected and out-of-the-way places. As an avid reader, I also enjoy riding shotgun on other people’s road trips. Yet while literature is filled with stories of journeys and pilgrimages of all kinds, there are surprisingly few books centered on climbing into a car and following the blacktop.
Perhaps that’s because the road trip is less about the destination than the space in between. Long hours behind the wheel create a pocket where the normal routines of life temporarily fall away. Conversation deepens, big questions have room to breathe, and long-held dreams can be laid bare. Familiar landscapes give way to unfamiliar ones, and it’s often in those places that we gain the clearest perspective on where we’ve been and where we’re headed. While something special happens in those liminal hours, it resists easy capture on the page. The five books below manage the feat. Across fiction and non-fiction, they explore the unique experience from different angles, while reminding us that sometimes the road itself is the highlight.
On the Road by Jack Kerouac
The road is life.
No novel is more synonymous with the American road trip than 1957’s On the Road. Jack Kerouac’s defining work of the Beat Generation barrels across the country with the same restless energy as its characters, following Sal Paradise and Dean Moriarty as they crisscross America in search of freedom and adventure. The prose is breathless, with episodes blurring together — and the whole book possesses a frenetic momentum that can leave readers feeling both exhilarated and exhausted.
It’s easy to dismiss On the Road as a novel that’s only meaningful when you’re a 20-something on the hunt for the secret to life. I expected exactly that when I first picked it up in my thirties. In some ways, the novel confirmed those expectations — its characters are forever in motion yet never seem to arrive anywhere.
But that’s also what makes the book endure. Read with a few more years under your belt, On the Road becomes less a celebration of perpetual movement than a meditation on it. Kerouac reminds us that we all need adventure — that life grows stagnant without occasional leaps into the unknown — but he also suggests that constant motion is a form of avoidance. The trick, as with so much in life, is finding the balance between settling down and never settling at all.
Zen and the Art of Motorcycle Maintenance by Robert Pirsig
Sometimes it’s a little better to travel than to arrive.
This unique book is part memoir, part philosophical treatise, and part father-son road trip. It can be bewildering and difficult at times — Pirsig frequently gets into long tangents about metaphysics, classical thought, and the elusive concept of “Quality.” I get that I’m not exactly selling it so far, but stick with me — the payoff is worth it.
Because beneath the dense ideas lies one of the most profound books ever written about craftsmanship and meaningful work. Over the course of a long road trip, Pirsig discovers and argues that quality is something we bring to every task through attention, care, and genuine engagement — it’s much more than just a final judgment on something. Whether you’re bringing an old bike back to life or doing something much more prosaic, the quality of your work ultimately reflects the quality of your soul.
Those ideas feel even more relevant today than when Pirsig published them in 1974. Zen and the Art of Motorcycle Maintenance is a compelling reminder that the good life isn’t built by consuming more things, but by caring more deeply about whatever is in front of you.
For more insights on the book, listen to Brett’s podcast with Mark Richardson, who came to understand and appreciate it by not only studying it, but recreating Pirsig’s road trip.
Harry Truman’s Excellent Adventure by Matthew Algeo
I like to take trips — any kind of trip. They are about the only recreation I have besides reading.
Harry Truman has long been one of my favorite presidents to read about, and this delightful little book offers a side of him that most histories overlook.
In the summer of 1953, just months after leaving the White House, Truman and his wife, Bess, climbed into their Chrysler and headed east on an unpublicized road trip. Truman had always loved automobiles and cared deeply about America’s roads. For a brief moment, he hoped he might simply become an ordinary citizen again. While it didn’t quite work that way — they would end up recognized everywhere they went — the Trumans enjoyed a retirement vacation in a way that no president since has been able to do.
Algeo tells this forgotten story with warmth and humor, including short detours into the history of America’s highways and road trips in general. It’s a charming glimpse into both Truman’s character and a version of America (and politics) that no longer exists.
Be sure to also check out Matthew’s fascinating podcast with Brett about the forgotten American sport of pedestrianism.
Travels With Charley by John Steinbeck
I am happy to report that in the war between reality and romance, reality is not the stronger.
When John Steinbeck set out to drive around America with his French poodle, Charley, he claimed he wanted to rediscover the country he’d spent his life writing about. The result is one of the great American travel narratives.
It’s also, almost certainly, not entirely true. If you’re expecting strict reportage, you’ll be disappointed. But that’s beside the point, frankly.
What Steinbeck beautifully and truthfully captured is the feeling of America in the early 1960s. The nation was on the cusp of enormous change: interstate highways were reshaping travel, regional identities were beginning to blur, and the old analog ways of doing things seemed to be quietly slipping away. His observations are funny, wistful, and occasionally melancholy — just like the unique characters he meets along the way.
At its heart, Travels With Charley is about paying close enough attention to notice what’s changing around you, what’s been lost already, and how to hold on to the good parts.
For a practical tip from the book, here’s Steinbeck’s clever way of doing laundry while you drive.
The Lincoln Highway by Amor Towles
How easily we forget — we in the business of storytelling — that life was the point all along.
A novel set in 1954, The Lincoln Highway follows 18-year-old Emmett Watson, newly released from a juvenile work farm, who intends to leave Nebraska with his younger brother and start a new life in California. Instead, two unexpected companions derail those carefully laid plans, sending the group east along the historic Lincoln Highway.
Like Towles’ other excellent novels, this one is filled with memorable characters, elegant prose, and a deep understanding of the stories people tell themselves about who they are and where they’re headed. The road itself and the boys’ character traits intertwine — every detour becomes a moral choice and every wrong turn opens new avenues.
The open road invites us to believe we’re in complete control, that with enough planning we can chart a perfect course from Point A to Point B. The Lincoln Highway is a good reminder that the most meaningful journeys rarely unfold according to plan and that sometimes the unexpected route proves to be the one worth taking.
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