Here are 100 books that On the Road fans have personally recommended if you like
On the Road.
Shepherd is a community of 11,000+ authors and super readers sharing their favorite books with the world.
Shepherd is reader supported. When you buy books, we may earn an affiliate commission.
As a travel writer, author, broadcaster, speaker, and producer, I’ve reported from over 100 countries on 7 continents for major print and digital publications worldwide and networks like National Geographic and Travel Channel. I kicked off my career with a solo, 12-month round-the-world backpacking adventure, largely inspired by the formative books I read below. Embracing the world with insatiable curiosity, an open heart, an open mind, a sense of humour, and enthusiasm to share my stories clearly resonated. Here I am, two decades later, author of a half-dozen bestselling books that focus on my own eclectic travels, which will hopefully inspire others as these books inspired me.
This book made me want to visit Antarctica, and when I finally did, I read it again.
There are a few things going on here: an insane adventure with a daring mission that defies the odds through incredible hardships; an introduction to that sparse, frozen continent that has long captivated the imagination; and a cosmic dissonance knowing modern travellers can visit such a harsh, unforgiving place today with the comfort of hot tubs, cocktail bars, and gourmet buffets.
Learning about the history of polar exploration makes your own journey that much more meaningful.
In August 1914, polar explorer Ernest Shackleton boarded the Endurance and set sail for Antarctica, where he planned to cross the last uncharted continent on foot. In January 1915, after battling its way through a thousand miles of pack ice and only a day's sail short of its destination, the Endurance became locked in an island of ice. Thus began the legendary ordeal of Shackleton and his crew of twenty-seven men. For ten months the ice-moored Endurance drifted northwest before it was finally crushed between two ice floes. With no options left, Shackleton and a skeleton crew attempted a near-impossible…
I sometimes describe myself as a stealth Zen teacher working in the business world. I've founded and been CEO of three companies, including the Search Inside Yourself Leadership Institute, a company I helped create and launch inside of Google's headquarters. I'm an executive coach and consultant to CEOs and leaders in the corporate and non-profit worlds. Prior to my business career I was a resident of the San Francisco Zen Center for 10 years. I'm the author of 5 books.
Siddhartha is a profound exploration of spirituality, self-discovery, and the pursuit of meaning in life.
It encourages readers to seek their own paths, embrace the present moment, and develop a deep sense of interconnectedness with the world around them. The books protagonist Siddhartha encounters various forms of suffering throughout his journey, and he comes to recognize the necessity and inevitability of pain and hardship in life.
The novel teaches that true wisdom and growth can arise from embracing and accepting suffering rather than trying to escape or avoid it.
Here the spirituality of the East and the West have met in a novel that enfigures deep human wisdom with a rich and colorful imagination.
Written in a prose of almost biblical simplicity and beauty, it is the story of a soul's long quest in search of he ultimate answer to the enigma of man's role on this earth. As a youth, the young Indian Siddhartha meets the Buddha but cannot be content with a disciple's role: he must work out his own destiny and solve his own doubt-a tortuous road that carries him through the sensuality of a love…
I’m drawn to the idea of doing what you think is right when others are against you because I’ve always felt the desire to row against the current and just do my own thing. I tend to avoid following the crowd because oftentimes I simply don’t agree with them. Am I being purposely difficult? Maybe. But I fear a society that goes with the flow simply because it’s easier and it doesn’t require them to think for themselves. It’s okay to listen to other people, but before you make any major decisions, ask yourself a question: Is this right for me?
Here’s my confession: I hated Chris McCandless by the time I finished this book. I hated his cockiness and lack of respect for the power of the wilderness.
But you know what I give him credit for? His ability to leave his life of privilege and the courage to go out into the world and forge his own destiny. He did what he thought was best for him despite the pushback he received from his friends and family.
I think I hated him so much because I wanted him to succeed, and he doomed himself through his own hubris.
Krakauer’s page-turning bestseller explores a famed missing person mystery while unraveling the larger riddles it holds: the profound pull of the American wilderness on our imagination; the allure of high-risk activities to young men of a certain cast of mind; the complex, charged bond between fathers and sons.
"Terrifying... Eloquent... A heart-rending drama of human yearning." —New York Times
In April 1992 a young man from a well-to-do family hitchhiked to Alaska and walked alone into the wilderness north of Mt. McKinley. He had given $25,000 in savings to charity, abandoned his car and most of his possessions, burned all…
Long before I became a filmmaker and many years before I knew what pre-history meant, I was a restless traveler. I was an adventurer and a hiker, fascinated by maps and mountain peaks and constantly searching for the best place for a coffee break. In my list, I have tried to combine my passion for traveling with what is really important in life: people, friends, and travel companions.
I wish I could be there, in the back seat of Steinbeck’s pickup truck…with a 10-year-old French poodle named Charlie.
Steinbeck's travelogue is a farewell to the America he knew and an observation of a country that is changing before his eyes. What a joy it could have been to join this great writer (and the poodle) if only for a part of his 10,000-mile road trip across the USA at the beginning of the 60s.
An intimate journey across America, as told by one of its most beloved writers
To hear the speech of the real America, to smell the grass and the trees, to see the colors and the light-these were John Steinbeck's goals as he set out, at the age of fifty-eight, to rediscover the country he had been writing about for so many years.
With Charley, his French poodle, Steinbeck drives the interstates and the country roads, dines with truckers, encounters bears at Yellowstone and old friends in San Francisco. Along the way he reflects on the American character, racial hostility, the…
I was born and raised in Northern California, right on the banks of the Sacramento River. While I didn’t realize it growing up, it was an epicenter for outdoor adventures. Along with skiing, snowboarding, hiking, wakeboarding, and camping, I always read a lot. My dad was worried that I would have no sense of direction because I was always in the back of our van or RV reading a book. That led to writing…and I had my first article published in a wakeboarding magazine when I was 15 years old. Traveling always took a backburner to reading, but now it’s front and center of my writing.
This is classic literature in the realm of American travel.
I had no idea that “blue highways” existed, and even though Heat-Moon went cross-country back in the 1970s in his van equipped with his igloo cooler and makeshift bed (not like the $100k fancy campers you find today), the type of people you meet and experiences you have in this amazing country are still relevant today.
In Blue Highways Revisited, I was shocked to read how long it took for this book to get published and the stacks of printed-out drafts he had of it (I think it was like four feet high). If there are any travel writing classes taught as part of a creative writing program, then Blue Highways better be on the list.
Hailed as a masterpiece of American travel writing, Blue Highways is an unforgettable journey along our nation's backroads. William Least Heat-Moon set out with little more than the need to put home behind him and a sense of curiosity about "those little towns that get on the map -- if they get on at all -- only because some cartographer has a blank space to fill: Remote, Oregon; Simplicity, Virginia; New Freedom, Pennsylvania; New Hope, Tennessee; Why, Arizona; Whynot, Mississippi." His adventures, his discoveries, and his recollections of the extraordinary people he encountered along the way amount to a revelation…
As a child, I moved with my family. I've moved for school. And I am not sure I could resurrect how many times my family moved for my journalism work. These books help me try to understand my wanderlust. Peter Laufer is an independent journalist, broadcaster, and documentary filmmaker working in traditional and new media. He is the James Wallace Chair in Journalism at the University of Oregon School of Journalism and Communication.
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.
Division Street, Studs Terkel's first book of oral history, established his reputation as America's foremost oral historian and as "one of those rare thinkers who is actually willing to go out and talk to the incredible people of this country" (in the words of Tom Wolfe).
Viewing the inhabitants of a single city, Chicago, as a microcosm of the nation at large, Division Street chronicles the thoughts and feelings of some seventy people from widely varying backgrounds in terms of class, race, and personal history. From a mother and son who migrated from Appalachia to a Native American boilerman, from…
As a child, I moved with my family. I've moved for school. And I am not sure I could resurrect how many times my family moved for my journalism work. These books help me try to understand my wanderlust. Peter Laufer is an independent journalist, broadcaster, and documentary filmmaker working in traditional and new media. He is the James Wallace Chair in Journalism at the University of Oregon School of Journalism and Communication.
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..."
French nobleman Alexis de Tocqueville's classic treatise on the American way of life.
Over 175 years ago, Alexis de Tocqueville, an astute political scientist, came to the United States to evaluate the meaning and actual functioning of democracy. Here, Tocqueville discusses the advantages and dangers of majority rule—which he thought could be as tyrannical as the rule of a monarchy. He analyzes the influence of political parties and the press on the government and the effect of equality on the social, political, and economic life of the American people. He also offers some startling predictions about world politics, which history…
I’ve known I was “special” since I was a child. I saw, felt, and heard things that others did not. Eventually I embraced my clairaudient mediumship gifts and turned it into a thriving business, allowing me to live a life of purpose: helping others find their passions and live their most joyful lives. But the journey never ends; I am always on a mission to transform. Consistently, literature has been where I turn when I am seeking wisdom on becoming the best version of myself. I also pursued certification as a Book Therapist - the first thing I’ll recommend to friends, family, or clients is the best book for their dilemma!
J.R.R. Tolkien's masterful storytelling is unmatched, and The Lord of the Rings weaves together moral dilemmas and profound philosophical ideas seamlessly, encouraging me to contemplate the nature of power, the importance of preserving the natural world, and the significance of individual choices.
The book's themes of heroism, friendship, sacrifice, and the struggle between good and evil resonate deeply. In addition, each of his characters feels like an aspect of oneself; the introspection it inspires is brilliant!
The Lord of the Rings instills a sense of wonder, ignites the imagination, and imparts timeless wisdom, which heavily transformed my perspective on life, my values, and my understanding of the human condition.
One Ring to rule them all, One Ring to find them, One Ring to bring them all and in the darkness bind them
In ancient times the Rings of Power were crafted by the Elven-smiths, and Sauron, the Dark Lord, forged the One Ring, filling it with his own power so that he could rule all others. But the One Ring was taken from him, and though he sought it throughout Middle-earth, it remained lost to him. After many ages it fell by chance into the hands of the hobbit Bilbo Baggins.
I’m an OB/GYN, passionate about adventuring beyond what’s expected. This has led me to pivot multiple times in my career, now focusing on writing. I’ve written a play, The Post-Roe Monologues, to elevate women’s stories. I cherish the curiosity that drives outer and inner exploration, and I love memoirs that skillfully weave the two. The books on this list feature extraordinary women who took risks, left comfort and safety, and battled vulnerability to step into the unknown. These authors moved beyond the stories they’d believed about themselves–or that others told about them. They invite you to think about living fuller and bigger lives.
I loved reading about a woman discovering her strength in the outdoors. This was the first book I read framed around a solo hiking trip but about deeper themes such as processing grief and searching for identity.
I was absorbed by the book’s masterful structure that weaves in these bigger themes while making me feel like I was on that trail with her. Strayed’s voice is captivating and witty, and her observations are wise. This book did not inspire me to hike solo – I’d done that already – but it inspired me to become a writer. An equally daunting challenge.
#1 NEW YORK TIMES BESTSELLER • A powerful, blazingly honest memoir: the story of an eleven-hundred-mile solo hike that broke down a young woman reeling from catastrophe—and built her back up again.
At twenty-two, Cheryl Strayed thought she had lost everything. In the wake of her mother’s death, her family scattered and her own marriage was soon destroyed. Four years later, with nothing more to lose, she made the most impulsive decision of her life. With no experience or training, driven only by blind will, she would hike more than a thousand miles of the Pacific Crest Trail from the…
I could say I’ve had a hard life (and I have), but who hasn’t? Life is one adversity after another, and we need all the help we can get. Without that help, moods suffer, hope falters, and our souls are diminished. During my own personal journey through this quagmire called life, I have often been lifted up and out of the mud whilst reading the books I suggest below and more. These books either made me laugh and cry, made me think, or made me change the way I approached things. Quite often, they did all four at the same time. Their insights were invaluable.
Whilst on humour (including satire): it is an important part of REBT. Humor is another one of those character strengths in positive psychology (again, good for you when used appropriately). It’s not for nothing that laughter is called the best medicine (in fact, I wrote my MSc dissertation on the use of humor in psychotherapy).
Humor, especially satire, and wordplay have helped me a lot in life. Regarding those two things, this book is the best bar none. Both funny and tragic (which sums life up pretty well), considering how much saber rattling is happening today, it’s as relevant now as it has always been.
I'm sure this book will change you for the better. It may also have you challenging authority a little more than you currently do (which alone will work wonders for your mental health and well-being).
Explosive, subversive, wild and funny, 50 years on the novel's strength is undiminished. Reading Joseph Heller's classic satire is nothing less than a rite of passage.
Set in the closing months of World War II, this is the story of a bombardier named Yossarian who is frantic and furious because thousands of people he has never met are trying to kill him. His real problem is not the enemy - it is his own army which keeps increasing the number of missions the men must fly to complete their service. If Yossarian makes any attempts to excuse himself from the…
