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 12,000+ authors and super readers sharing their favorite books with the world.

When you buy books, we may earn a commission that helps keep our lights on (or join the rebellion as a member).

Book cover of Endurance

John T. Hancock Author Of Why Elephants Cry: How Observing Unusual Animal Behaviours Can Predict the Weather (and Other Environmental Phenomena)

From my list on environment having a significant impact.

Why am I passionate about this?

I have always loved science and luckily had inspirational teachers at school and university. I ended up being a professor of molecular biology, but animal behavior has always fascinated me. Watching a total eclipse of the sun near my parents’ house in Cornwall when horses started to behave unusually before the darkness fell piqued my interest in writing my book. Did they know it was coming? Reading about Dolbear’s Law using crickets to measure the air temperature led me to ask what was going on. The more reading I did, the more amazing stories became revealed, and it seemed timely to put this passion into a book. 

John's book list on environment having a significant impact

John T. Hancock Why did John love this book?

I loved this book as it tells an incredible story of the fight against the environment. Even though I knew how the adventure ended, I was still gripped, wondering what happened and how the people involved fought for their survival.

Understanding the “land” on which they found themselves and watching some of the animal behavior was key to their perseverance, even after they lost their ship. Although this is a true story, I still found it hard to believe that it really happened, and Lansing’s writing really brings the hardship they suffered and their bravery alive. 

By Alfred Lansing,

Why should I read it?

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

What is this book about?

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…


Book cover of Siddhartha

Sarah Cavallaro Author Of Dogs Have Angels too

From my list on human condition themes.

Why am I passionate about this?

I am on a self-discovery journey, and each day, I discover more of why I am here on earth. The books I mentioned all have themes related to the human condition. I write to express what I understand. I love writing about characters and their journeys. I love all animals, and dogs are a great comfort. I’d like to see animal abuse come to an end in my lifetime. I write about people who have fallen from great heights and how saving animals and others in need saves them. We need to love more.

Sarah's book list on human condition themes

Sarah Cavallaro Why did Sarah love this book?

I loved the arduous human journey that became a great spiritual one. It was about how Buddha became Buddha. That can only happen when one goes beyond their own comforts and reaches within for faith to continue to understand yourself and others. This book deeply influenced my writing and my life.

By Hermann Hesse,

Why should I read it?

14 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

Mindy Vail Author Of The MindShift Effect: Where Change Management is Redefined and Leadership is Refined

From my list on being authentic and empowered.

Why am I passionate about this?

I’m Mindy Vail, and with over 25 years in education and change management, I’ve spent my career as a leadership consultant and keynote speaker. My passion for the book list I’ve put together comes from my work in guiding individuals and organizations through transformation and my dedication to helping others find their joy. Each book reflects my commitment to embracing change, nurturing leadership, and unlocking potential. My insights come from hands-on experience and a deep understanding of psychology, leadership, and personal growth, and I believe we are all ever-evolving in our journeys.

Mindy's book list on being authentic and empowered

Mindy Vail Why did Mindy love this book?

This book captivates me because Chris McCandless's quest for meaning and self-discovery mirrored my own struggles with never wanting to fit into a box determined by others. His desire to break free from societal constraints and find true fulfillment resonates with my own experiences. Jon Krakauer’s portrayal of McCandless’s adventure into the wilderness also strikes a chord with me, highlighting the extremes people go to in their pursuit of purpose and the consequences of those choices.

Reading it reminds me of the importance of embracing our own paths, even when they diverge from the norm and the profound insights that can come from stepping into the unknown.

By Jon Krakauer,

Why should I read it?

19 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

Geoffrey Morrison Author Of Budget Travel For Dummies

From my list on inspire travel road trips to international fun.

Why am I passionate about this?

For the last decade, I’ve spent the majority of each year traveling. I’ve been to 60 countries across 6 continents and every US state. My love of travel was inspired and encouraged by my parents from a very early age. I’ve also been inspired by a wide variety of other sources, like movies, TV, photography, and, of course, books. Often, I’ll plan an adventure around a cool location I saw or read about and then just go. I’ll just show up and see what happens. All it takes is that little initial nudge, like what I found in these books.

Geoffrey's book list on inspire travel road trips to international fun

Geoffrey Morrison Why did Geoffrey love this book?

This is the quintessential American road trip travelogue by one of America’s greatest novelists. Written towards the end of his life, after driving literally around the country with his faithful poodle Charley, it’s a remarkable, if sometimes probably fictionalized or at least embellished, snapshot of the country in late 1960.

Some language and aspects throughout are definitely “of its time,” but so many insights and perspectives could have easily been written about the modern US. It’s a testament to the power and wonder of a good road trip that is sometimes funny, sometimes nostalgic, sometimes heart-wrenching, but always captivating. 

By John Steinbeck,

Why should I read it?

16 authors picked Travels with Charley 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?

54 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

Jackie Jarvis Author Of Transform Your Life by Walking: Powerful Messages Walking Camino Pilgrimages

From my list on hiking trails that inspire you to do it yourself.

Why am I passionate about this?

I am a passionate long-distance hiker and regularly enjoy local walks close to where I live in Oxfordshire. Over the years, I have walked many long-distance trails, including Camino Pilgrimages. The books I am sharing are those that have inspired my own walking adventures and self-reflection. I am a big believer in the benefits of walking for mind, body, and spirit, and I personally enjoy those benefits daily. My passion for walking and the depth of thinking it can help you attain has found its way into both my personal and business life. Walking to me is life!

Jackie's book list on hiking trails that inspire you to do it yourself

Jackie Jarvis Why did Jackie love this book?

I loved this book because I could relate to the tough, emotional place the author was in when she made this epic journey. Her rucksack was extremely heavy. It felt like it represented the burden she was carrying at the time. I loved the unfolding of both her physical and emotional journey, how much she learned about herself, and how much she was eventually able to let go of to enable her to move forward.

Reading this book motivated me to go on a similar journey, hiking many of the Camino Pilgrimage routes. This was a book I thought about long after I had finished reading it. It had the kind of truth about it that stays with you. 

By Cheryl Strayed,

Why should I read it?

31 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

Matthew Evangelista Author Of Allied Air Attacks and Civilian Harm in Italy, 1940-1945: Bombing among Friends

From my list on allied liberation of Italy during World War II.

Why am I passionate about this?

I fell in love with Italy the first time I visited as a graduate student. Later, as a professor spending extended periods there with my family, I began investigating Italy’s experience of World War II. I was inspired by the diary of Iris Origo, an Anglo-American who lived in rural Tuscany. She reported of civilians bombed by Allied aircraft and strafed by machine guns from the air—even after Italy had surrendered. In my quest to understand the relations between the Allies and Italian civilians, I came upon a trove of great wartime novels, many recently back in print, and I am eager to share my enthusiasm for them.

Matthew's book list on allied liberation of Italy during World War II

Matthew Evangelista Why did Matthew love this book?

I encountered this book backward. As a teenager growing up at the end of the US war in Vietnam, I read the Mad magazine spoof of the movie version long before I saw the movie itself, and then I read the novel. I focused on the antiwar theme and the concern of the bomber crew to get home without getting shot down.

The novel was based on Heller’s wartime experience, but I hardly realized it was about bombing Italy until I discovered the papers one of his crewmates had donated to Cornell University. I learned how many of the episodes were based on real incidents, including the only time the novel focuses on Italian civilians—when the crew objects to destroying an Italian Alpine village of no military significance. 

By Joseph Heller,

Why should I read it?

18 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 Endurance
Book cover of Siddhartha
Book cover of Into the Wild

Share your top 3 reads of 2024!

And get a beautiful page showing off your 3 favorite reads.

1,355

readers submitted
so far, will you?

5 book lists we think you will like!

Interested in Beat Generation, road trips, and New Jersey?

Beat Generation 8 books
Road Trips 28 books
New Jersey 80 books