100 books like On the Road

By Jack Kerouac,

Here are 100 books that On the Road fans have personally recommended if you like On the Road. Shepherd is a community of 10,000+ authors and super readers sharing their favorite books with the world.

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Book cover of Siddhartha

Marc Lesser Author Of Finding Clarity: How Compassionate Accountability Builds Vibrant Relationships, Thriving Workplaces and Meaningful Lives

From my list on helping you live a meaningful and successful life.

Why am I passionate about this?

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.

Marc's book list on helping you live a meaningful and successful life

Marc Lesser Why did Marc love this book?

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.

By Hermann Hesse,

Why should I read it?

13 authors picked Siddhartha as one of their favorite books, and they share why you should read it.

What is this book about?

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…


Book cover of Into the Wild

M. R. Reed Author Of Enthrall

From my list on doing what is right when others are against you.

Why am I passionate about this?

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?

M. R.'s book list on doing what is right when others are against you

M. R. Reed Why did M. R. love this book?

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. 

By Jon Krakauer,

Why should I read it?

18 authors picked Into the Wild as one of their favorite books, and they share why you should read it.

What is this book about?

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…


Book cover of Travels with Charley in Search of America

Eyal Halfon Author Of They Were Here Before Us: Stories from Our First Million Years

From my list on traveling the world from your armchair.

Why am I passionate about this?

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.

Eyal's book list on traveling the world from your armchair

Eyal Halfon Why did Eyal love this book?

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.

By John Steinbeck,

Why should I read it?

13 authors picked Travels with Charley in Search of America as one of their favorite books, and they share why you should read it.

What is this book about?

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…


Book cover of Blue Highways

Kayla Anderson Author Of Moon Northern California Road Trip: Drives along the Coast, Redwoods, and Mountains with the Best Stops along the Way

From my list on embarking on epic adventures from your armchair.

Why am I passionate about this?

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. 

Kayla's book list on embarking on epic adventures from your armchair

Kayla Anderson Why did Kayla love this book?

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. 

By William Least Heat-Moon,

Why should I read it?

9 authors picked Blue Highways as one of their favorite books, and they share why you should read it.

What is this book about?

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…


Book cover of Division Street: America

Peter Laufer Author Of Up Against the Wall: The Case for Opening the Mexican-American Border

From my list on the middle of america from New Jersey to Oakland.

Why am I passionate about this?

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.

Peter's book list on the middle of america from New Jersey to Oakland

Peter Laufer Why did Peter love this book?

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.

By Studs Terkel,

Why should I read it?

1 author picked Division Street as one of their favorite books, and they share why you should read it.

What is this book about?

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…


Book cover of Democracy in America

Peter Laufer Author Of Up Against the Wall: The Case for Opening the Mexican-American Border

From my list on the middle of america from New Jersey to Oakland.

Why am I passionate about this?

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.

Peter's book list on the middle of america from New Jersey to Oakland

Peter Laufer Why did Peter love this book?

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..."

By Alexis de Tocqueville,

Why should I read it?

1 author picked Democracy in America as one of their favorite books, and they share why you should read it.

What is this book about?

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…


Book cover of The Lord of the Rings

Claudia Amendola Alzraa Author Of The Transformational Path: How Healing, Unlearning, and Tuning into Source Helped Me Manifest My Most Abundant Life

From my list on completely transforming your life.

Why am I passionate about this?

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!

Claudia's book list on completely transforming your life

Claudia Amendola Alzraa Why did Claudia love this book?

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.

By J.R.R. Tolkien,

Why should I read it?

52 authors picked The Lord of the Rings as one of their favorite books, and they share why you should read it. This book is for kids age 14, 15, 16, and 17.

What is this book about?

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.

From Sauron's fastness in the Dark Tower of…


Book cover of Wild: From Lost to Found on the Pacific Crest Trail

Jim Landwehr Author Of Dirty Shirt: A Boundary Waters Memoir

From my list on the trials and joys of outdoor adventure.

Why am I passionate about this?

I have been a lover of all things outdoors since I was a boy. After my father was killed at a young age, my brothers and I took his love for outdoor adventure and made it our own. Fully aware of all that can go wrong, my brothers and I went into our ventures with a keen sense of humor. Camping, fishing, and kayaking all come with their own challenges and requisite hilarious moments. It is these moments of adversity, and personal risk, that are sometimes lightened by a good dose of laughter and levity.

Jim's book list on the trials and joys of outdoor adventure

Jim Landwehr Why did Jim love this book?

Much like A Walk in the Woods, Wild takes an ordinary person and puts them in an extremely challenging environment only to show they were unprepared for the rigors of the great outdoors.

Strayed has a similar goal to Bryson, but chooses the Pacific Crest Trail. The hike is an attempt at self-discovery as well as to challenge herself after experiencing various addictions and the loss of her mother. Strayed’s motives are not unlike those of my brothers and I as we ventured into the BWCAW while navigating our young lives as twenty-somethings.

By Cheryl Strayed,

Why should I read it?

27 authors picked Wild as one of their favorite books, and they share why you should read it.

What is this book about?

#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…


Book cover of Catch-22

Adam Kuper Author Of The Museum of Other People: From Colonial Acquisitions to Cosmopolitan Exhibitions

From my list on books that helped me to grow up.

Why am I passionate about this?

I grew up in white South Africa, a racist, philistine, authoritarian, and puritanical society. The first four books I have chosen appeared in the 1950s, and I read them in my teens. Catch-22 was published in the ‘60s, but all five heroes–or anti-heroes–of these novels were of the same generation, about ten years my senior, so they were perfectly placed to be role models. They were rebels and mavericks, and except for Yossarian, they were all would-be writers. I recognised a kinship with them and took them as my guides into adulthood. And so I left for Paris and became a writer and an anthropologist. No regrets.

Adam's book list on books that helped me to grow up

Adam Kuper Why did Adam love this book?

This book is set during World War II. Captain John Yossarian, bombardier, has a hard time maintaining his sanity, let alone keeping alive. His crazed commander demands that the crew fly ever more dangerous missions. Yossarian realises a terrible truth: “The enemy is anybody who's going to get you killed, no matter which side he's on.” When men request leave because they are going crazy, the camp doctor explains the catch-22. "Anyone who wants to get out of combat duty isn't really crazy."

Yossarian’s predicament was more extreme, his adults more dangerous, but like my other big brothers, he insisted on doing things his way.

By Joseph Heller,

Why should I read it?

15 authors picked Catch-22 as one of their favorite books, and they share why you should read it.

What is this book about?

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…


Book cover of Eat Pray Love

Jessica Hepburn Author Of Save Me from the Waves: An adventure from sea to summit

From my list on females adventure and change their life.

Why am I passionate about this?

I am an author and adventure activist who believes passionately in the power of big and small adventures to change your life for the better when you’ve been through dark and difficult times. I have written three books, all of which I describe as ‘alternative adventure stories’ because they don’t look like the usual ‘Boy’s Own’ tales of danger and derring-do (although they do include some of that, too!). I’m drawn to the words of wonderful women warriors who give me strength in times of sadness. These books have inspired me to live big and bravely in what is often a challenging but (mainly) wonderful world.

Jessica's book list on females adventure and change their life

Jessica Hepburn Why did Jessica love this book?

This is a book that changed my life. In fact, I probably want to be Elizabeth Gilbert. Witty, wise, and wonderful, it made me want to go to Italy to eat, to pilgrimage to India to pray, to fall in love in Bali, and to write about that journey.

I read it nearly twenty years ago and it still inspires me today.

By Elizabeth Gilbert,

Why should I read it?

8 authors picked Eat Pray Love as one of their favorite books, and they share why you should read it.

What is this book about?

_________________ OVER 15 MILLION COPIES SOLD WORLDWIDE _________________ 'Eat, Pray, Love has been passed from woman to woman like the secret of life' - Sunday Times 'A defining work of memoir' - Sunday Telegraph 'Engaging, intelligent, and highly entertaining' - Time _________________ It's 3 a.m. and Elizabeth Gilbert is sobbing on the bathroom floor. She's in her thirties, she has a husband, a house, they're trying for a baby - and she doesn't want any of it. A bitter divorce and a turbulent love affair later, she emerges battered and bewildered and realises it is time to pursue her own…


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