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

Trish MacEnulty Author Of The Hummingbird Kiss: My Life as an Addict in the 1970s

From my list on memoirs about or by addicts, drunks, and f#@k ups.

Why am I passionate about this?

I am a recovered (not “recovering”) addict and writer. These days I write historical fiction because I enjoy an escape from present-day reality, and research is fun. But I started writing as a way to make sense of my chaotic world and in hopes of healing myself. Something was broken inside me, and I didn’t know how to fix it. So I wrote about the shadowy realms of my life and kept on writing until somehow I was able to let go of the past and create a different life, one which would not land me upside down in a ditch with my neck broken and my tires spinning. 

Trish's book list on memoirs about or by addicts, drunks, and f#@k ups

Trish MacEnulty Why did Trish love this book?

I read this book sitting on the balcony of a condo at the beach. I got a sunburn because I couldn’t put it down.

Cheryl’s trek along the PCT is weirdly harrowing and heart-warming as she meets creeps, clowns, and kindred folk. But what makes the book so compelling for me is how Cheryl delves into her need for this test of her resolve, which is to figure out what went wrong with her life after her mother’s death and how to fix it.

I was with her every step of the way and felt as if I, too, had conquered the PCT and overcome my misbegotten past. The honesty of her self-examination nailed this book to my heart. 

By Cheryl Strayed,

Why should I read it?

24 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 Eat Pray Love

Kristen Van Nest Author Of Where to Nest: A Global Search for Love, Cheap Wine and a Place to Belong

From my list on travel books that’ll make you laugh until your side hurts.

Why am I passionate about this?

With my debut comedic travel memoir having come out in April, I read every humorous travel book I could get my hands on both as part of my education for inspiration on how to write my book and before I even knew I was going to write a book because I simply love reading these types of stories. From my own experience, travel has made me grow so much as a person, and all of these authors beautifully capture their own journeys and how travel helped them find their way.

Kristen's book list on travel books that’ll make you laugh until your side hurts

Kristen Van Nest Why did Kristen love this book?

This book was revolutionary in its time because it was very rare at the time of publication that someone could go abroad to really discover themselves.

Gilbert forcing herself to focus on the absolute most terrifying thing–your own areas for growth–leads her into dark places, but also the bright light at the end of the tunnel that comes with doing this type of self work. It was quite enjoyable joining her on this journey and what each place she visited taught her.

By Elizabeth Gilbert,

Why should I read it?

7 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…


Book cover of The Unlikely Thru-Hiker: An Appalachian Trail Journey

Heather Anish Anderson Author Of Mud, Rocks, Blazes: Letting Go on the Appalachian Trail

From my list on for hikertrash and other vagabonds.

Why am I passionate about this?

National Geographic Adventurer of the Year, Heather Anderson is the only woman who has completed the Appalachian, Pacific Crest, and Continental Divide National Scenic Trails each three times. This includes her historic Calendar Year Triple Crown hike in 2018 when she hiked all three of those trails in one March-November season, making her the first female to do so. As an itinerant hiker, runner, and mountaineer she has logged over 40,000 foot miles since 2003 including over a dozen thru-hikes and many ultramarathons. She is also an avid mountaineer and peakbagger working on several ascent lists in the US and abroad.

Heather's book list on for hikertrash and other vagabonds

Heather Anish Anderson Why did Heather love this book?

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.

By Derick Lugo,

Why should I read it?

1 author picked The Unlikely Thru-Hiker as one of their favorite books, and they share why you should read it.

What is this book about?

Derick Lugo had never been hiking. He certainly couldn't imagine going more than a day without manicuring his goatee. But with a job cut short and no immediate plans, this fixture of the New York comedy scene began to think about what he might do with months of free time. He had heard of the Appalachian Trail, but he had never seriously considered attempting to hike all 2,184.2 miles of it. Suddenly he found himself asking, Could he do it? 
 
The Unlikely Thru-Hiker is the story of how a young black man from the city, unfamiliar with both the outdoors…


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