Even as a 38-year-old man, I still love the feeling of heading out on road trips. They promise freedom, romance and adventure without the increased difficulty of flight. All you need is a full tank of gas, a map (a paper one still has value!), and a willingness to explore unexpected and far-flung places. As an avid reader, I also enjoy riding shotgun on other people’s road trips. Yet while literature is full of stories of all kinds of journeys and pilgrimages, there are surprisingly few books that focus on hopping into a car and following the blacktop.
Maybe it’s because the road trip is less about the destination from the middle place. Driving for long periods of time can create a place where the normal routines of life temporarily cease to exist. Conversations deepen, big questions get room to breathe, and long-held dreams can be laid bare. Familiar landscapes give way to unfamiliar ones, and it is often in those places that we gain clear perspective on where we have been and where we are going. While something special happens in those final hours, it resists easy capture on the page. The five books below manage this feat. In fiction and non-fiction, they explore unique experiences from different angles, while reminding us that sometimes the road is the highlight.
on the way by jack kerouac
Road is life.
No novel is more synonymous with the American road trip than 1957 on the way. Jack Kerouac’s defining work of the Beat Generation is performed with the same restless energy as its characters across the country, including Sal Paradise and Dean Moriarty, traveling across America in search of freedom and adventure. The prose is breathless, the links blur together – and there’s a frenetic pace throughout the book that can leave readers feeling both exhilarated and exhausted.
it’s easy to dismiss on the way As a novel it only makes sense if you’re 20 and searching for the mystery of life. This is exactly what I expected when I first picked it up in my thirties. In some ways, the novel confirmed those expectations – its characters are always on the move yet never seem to get anywhere.
But this is also what sustains the book. Read on with a few more years under your belt, on the way It becomes less a celebration of perpetual motion and more like a meditation on it. Kerouac reminds us that we all need adventure – that life tends to be stagnant without the occasional leap into the unknown – but he also suggests that constant motion is a form of avoidance. Like much in life, the trick is to strike a balance between settling and never compromising.
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. This can be confusing and difficult at times – Pirsig often goes on at length about metaphysics, classical thought, and the elusive concept of “quality”. I guess I’m not quite sold on it yet, 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. During a long road trip, Pirsig discovered and argued that quality is something we bring to every task through attention, care and genuine engagement – it is much more than a final decision on something. Whether you’re bringing an old bike back to life or doing something more professional, the quality of your work ultimately reflects the quality of your soul.
Those ideas seem more relevant today than when Pirsig published them in 1974. Zen and the art of motorcycle maintenance It’s a compelling reminder that the good life is not made by consuming more things, but by caring more deeply about what is in front of you.
For more information on the book, Listen to Brett’s podcast with Mark Richardson, Who not only studied it, understood and appreciated it, but also recreated Pirsig’s road trip.
The excellent adventure of harry truman By Matthew Algeo
I love to travel – any kind of travel. These are my only entertainment other than reading.
Harry Truman has long been one of my favorite presidents to read about, and this delightful little book presents a side of him that most histories ignore.
In the summer of 1953, just a few months after leaving the White House, Truman and his wife, Bess, climbed into their Chrysler and headed east on an unpublicized road trip. Truman always loved automobiles and cared deeply for America’s roads. For a brief moment, he hoped that he could become a normal citizen again. Although it didn’t work out that way—he would eventually be recognized wherever he went—Truman enjoyed the retirement holidays in a way that no president since has been able to do.
Algeo tells this forgotten story with warmth and humor, including little twists in the history of America’s highways and road trips in general. It’s a fascinating glimpse into Truman’s character and a version of America (and politics) that no longer exists.
Be sure to check out Matthew as well Fascinating podcast with Brett about the forgotten American sport of walking.
trip with charlie by john steinbeck
I’m happy to report that reality is not stronger in the war between reality and romance.
When John Steinbeck set out to drive around America with his French poodle, Charlie, he claimed he wanted to rediscover the country he had spent his life writing about. The result is one of the great American travelogues.
This is also, almost certainly, not entirely true. If you’re expecting rigorous reporting, you’ll be disappointed. But to be honest, this is a different matter.
What Steinbeck captured beautifully and truthfully is Feeling America in the early 1960s. The nation was on the cusp of enormous change: Interstate highways were reshaping travel, regional identities were beginning to fade, and old analog ways of doing things seemed to be quietly coming to an end. His comments are funny, mournful and sometimes sad – just like the unique characters he meets along the way.
in its heart, trip with charlie It’s about noticing what’s changing around you, what’s been lost, and how to keep the good parts intact.
For practical tips from the book, Here’s Steinbeck’s clever way to do laundry while you drive.
Lincoln Highway by amor towels
How easily we forget – we are in the business of telling stories – that life was the purpose all along.
A novel based on the 1954 Lincoln Highway Follows 18-year-old Emmett Watson, recently 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, and send the group heading east along the historic Lincoln Highway.
Like Towles’s other excellent novels, this one is filled with memorable characters, elegant prose, and a keen sense of the stories people tell themselves about who they are and where they’re going. The road itself and the boys’ character traits are intertwined – each turn becomes a moral choice and each wrong turn opens new paths.
The open road invites us to believe that we are in complete control, that with enough planning we can determine a perfect route from point A to point B. Lincoln Highway It’s a good reminder that the most meaningful journeys rarely go according to plan and sometimes the unexpected path proves worth taking.
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