Here are 100 books that The Oregon Trail fans have personally recommended if you like The Oregon Trail. Shepherd is a community of 12,000+ authors and super readers sharing their favorite books with the world.

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Book cover of Skyfaring: A Journey with a Pilot

Martha W. Murphy Author Of CRU Oyster Bar Nantucket Cookbook: Savoring Four Seasons of the Good Life

From my list on the eclectic reader of nonfiction.

Why am I passionate about this?

I’m a narrative nonfiction writer interested in a broad range of topics, including but not limited to: food and the people who bring it to us; travel and life in faraway places; human health and the role of medicine; memoir as one person’s story yet illustrative of the human spirit; and the unique and remarkable role dogs play in our lives. I am the same kind of reader: I read across a range of topics, mostly nonfiction. The bookshelves in my house and the record of titles I’ve checked out from my local library show an eclectic taste, as do the books I’m recommending here. I hope you’ll enjoy them!

Martha's book list on the eclectic reader of nonfiction

Martha W. Murphy Why Martha loves this book

I expected a book of insider stories about the hidden world of commercial airline travel from the people who make it possible, but instead I found a beautifully written, lyrical, and awestruck look at what it means to travel high above the Earth’s surface day after day, zooming between cities on opposite sides of the world.

I have never had the physics of flight, gravitational pull, wind, storms, and clouds explained so clearly and compellingly. I frequently reread passages for their beauty and emotion and completely unique fresh perspective. I knew flying was a sophisticated skill, but this book made it clear how truly complex a pilot’s job is.

The author’s love of his hard-won occupation is enthralling, making this a book to share with aspiring aviators in your life.  

By Mark Vanhoenacker ,

Why should I read it?

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

What is this book about?

**Sunday Times Bestseller**
**Book of the Week on Radio 4**

'One of the most constantly fascinating, but consistently under-appreciated aspects of modern life is the business of flying. Mark Vanhoenacker has written the ideal book on the subject: a description of what it's like to fly by a commercial pilot who is also a master prose stylist and a deeply sensitive human being. This is a man who is at once a technical expert - he flies 747s across continents - and a poet of the skies. This couldn't be more highly recommended.' Alain de Botton

Think back to when…


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Book cover of The High House

The High House by James Stoddard,

The Victorian mansion, Evenmere, is the mechanism that runs the universe.

The lamps must be lit, or the stars die. The clocks must be wound, or Time ceases. The Balance between Order and Chaos must be preserved, or Existence crumbles.

Appointed the Steward of Evenmere, Carter Anderson must learn the…

Book cover of Unbroken

T.J. Derry Author Of Carried Away

From my list on readers seeking more from modern life.

Why am I passionate about this?

I didn’t sit down to write Carried Away with a personal sermon in my back pocket. No buried lessons or hidden curriculum—it was just a story I wanted to tell. But stories have a way of outsmarting you. 

So when I chose these books, I wasn’t looking for perfect comparisons—I was looking for echoes. Some of these books will drag you through POW camps or strand you on a lifeboat with a tiger; others will lean in and whisper that you’ve been running a program and calling it personality. A few say the quiet part out loud—about grit, meaning, and purpose. Others ring you up with fable, abstractions, or science, but they leave their mark just the same. 

T.J.'s book list on readers seeking more from modern life

T.J. Derry Why T.J. loves this book

Almost impossible to put down—this was the first book that made me physically feel the words.

I wouldn’t call it enjoyable in the usual sense; the experience was excruciating. But that’s exactly what makes it unforgettable. Hillenbrand’s prose, paired with the true story of Louis Zamperini’s plunge from Olympic track star to the unrelenting hell of a POW camp, smacks you off your cozy little couch and right into a world where Sleepytime tea, candles, and Netflix don’t exist.

What struck me most was how it captured not only the brutality of survival, but the stubborn, almost irrational resolve of the human spirit—and the possibility of forgiveness that would defy logic. This isn’t a book that’s light to hold—it’s grit, torment, and triumph in equal parts. I recommend it because it inspires without sugarcoating—harrowing and uplifting in the same breath.

For anyone who wants proof of just how deep the…

By Laura Hillenbrand ,

Why should I read it?

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

What is this book about?

From the author of the bestselling and much-loved Seabiscuit, an unforgettable story of one man's journey into extremity. On a May afternoon in 1943, an Army Air Forces bomber crashed into the Pacific Ocean and disappeared, leaving only a spray of debris and a slick of oil, gasoline, and blood. Then, on the ocean surface, a face appeared. It was that of a young lieutenant, the plane's bombardier, who was struggling to a life raft and pulling himself aboard. So began one of the most extraordinary odysseys of the Second World War. The lieutenant's name was Louis Zamperini. In boyhood,…


Book cover of A Walk in the Woods: Rediscovering America on the Appalachian Trail

Jack Rathmell Author Of How the Rhino Lost His Horn

From my list on navigating a world you're not cut out for.

Why am I passionate about this?

I’ve felt like a fish out of water for most of my life. My mom’s English and my dad’s from Pennsylvania, so growing up it was always difficult to figure out who I was, where was “home.” So I always felt uneasy and self-conscious about not fitting in, wherever I happened to be. I always felt vaguely homesick for somewhere else. Reading was one way I could escape, travel was another, more literal way. Which is how I ended up in South Africa, where I eventually got my master's in journalism/international politics. (And my adventures there, of course, led to my book.)

Jack's book list on navigating a world you're not cut out for

Jack Rathmell Why Jack loves this book

I loved this book because it shows that the setting/particulars of the “journey” don’t actually matter.

It’s all about the author’s voice, perspective, and, in this case, their sense of humor. If these aspects are unique and engaging, it doesn’t matter where they went, or if you have any interest in seeing/doing those things for yourself.

I’ve always felt like I can resonate more with people that are willing to admit their fallibility, and even draw attention to/make light of it. To just how ignorant or clumsy or hapless or cowardly they are. I think that always makes for a better, more human story, a better connection with the reader.

On top of all this, I have a soft spot for the Appalachian Trail, since it crosses through Pennsylvania, only a few miles from where I grew up.

By Bill Bryson ,

Why should I read it?

14 authors picked A Walk in the Woods as one of their favorite books, and they share why you should read it.

What is this book about?

From the author of "Notes from a Small Island" and "The Lost Continent" comes this humorous report on his walk along the Appalachian Trail. The Trail covers 14 states and over 2000 miles, and stretches along the east coast of America from Maine in the north to Georgia in the south. It is famous for being the longest continuous footpath in the world. It snakes through some of the wildest and most specactular landscapes in America, as well as through some of its most poverty-stricken and primitive backwoods areas.


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Book cover of The Guardian of the Palace

The Guardian of the Palace by Steven J. Morris,

The Guardian of the Palace is the first novel in a modern fantasy series set in a New York City where magic is real—but hidden, suppressed, and dangerous when exposed.

When an ancient magic begins to leak into the world, a small group of unlikely allies is forced to act…

Book cover of Being Mortal: Medicine and What Matters in the End

John S. Tregoning Author Of Live Forever?

From my list on ageing well and living a meaningful life.

Why am I passionate about this?

On reaching my late 40’s, the topic of ageing and dying raised its head with a clarion call. This wake up call led me to draw upon my 25 years’ experience as a scientist to research why we age, how we die, and what (if anything) we can do about it all. I also looked beyond the physical into the social and emotional aspects. These book recommendations reflect my journey to understanding that a life well lived is about doing things you like with people you love, rather than swallowing vitamin pills.

John's book list on ageing well and living a meaningful life

John S. Tregoning Why John loves this book

This book completely changed the way I thought about aging and death. I listened to this book whilst walking along the Cornish Coastal Path in January. I was in the process of writing my own book about aging and had been focusing on biology but not humanity.

The warmth of the writing, the emotional journey that Gawande undergoes, the brilliant advice, and the wisdom from an expert all combine to make a wonderful life (and death) changing book.

By Atul Gawande ,

Why should I read it?

17 authors picked Being Mortal as one of their favorite books, and they share why you should read it.

What is this book about?

THE INTERNATIONAL BESTSELLER

'GAWANDE'S MOST POWERFUL, AND MOVING, BOOK' MALCOLM GLADWELL

'BEING MORTAL IS NOT ONLY WISE AND DEEPLY MOVING; IT IS AN ESSENTIAL AND INSIGHTFUL BOOK FOR OUR TIMES' OLIVER SACKS

For most of human history, death was a common, ever-present possibility. It didn't matter whether you were five or fifty - every day was a roll of the dice. But now, as medical advances push the boundaries of survival further each year, we have become increasingly detached from the reality of being mortal. So here is a book about the modern experience of mortality - about what it's…


Book cover of Around the World in Eighty Days

Gary Orleck Author Of Travels With Maurice: An Outrageous Adventure in Europe, 1968

From my list on life and it's changes – the what, where, and why.

Why am I passionate about this?

At 13 years old I told my father that “I will be travelling around the USA as soon as I graduate college." It took 10 days to prepare but prepare and depart I did. I worked my way around the USA for 6 months and on the way home I told my Dad, “Next is Europe.” A year later I traveled with the son of the richest man in the world and the adventures we had driving 19,865 miles through 12 European countries for 10 weeks were both mind-blowing and life-changing. My passion for traveling and life shows throughout my book, and I assure you that you'll enjoy travelling along with me. 

Gary's book list on life and it's changes – the what, where, and why

Gary Orleck Why Gary loves this book

After you remind yourself that this story is taking place in 1872, you can just sit back and have fun with it as you will come to see that it is a very clever story and true to the time period it is set in.

I advise that you should let your mind wander, and you will very easily fall in love with the well-defined characters and the suspense of the story. Have we not all raced against time in our own lifetime? It is a really fun read, especially if you use your imagination to join in, and that is why I believe that everybody should read this classic story at least once in their lifetime.

By Jules Verne ,

Why should I read it?

3 authors picked Around the World in Eighty Days as one of their favorite books, and they share why you should read it.

What is this book about?

Some novels are considered classics of children literature, read by numerous generations of young readers who made them immortal. That is the case with Around the World in Eighty Days by Jules Verne, a true prototype for many later adventure tales. The thrilling race against time of eccentric Phileas Fogg and his manservant Passepartout, having to run around the planet to win a bet, is here presented in a modern and original way, thanks to the splendid drawings by Francesca Rossi, an artist able to capture the vivid atmosphere of the story.


Book cover of The Cafe on the Edge of the World

Gary Orleck Author Of Travels With Maurice: An Outrageous Adventure in Europe, 1968

From my list on life and it's changes – the what, where, and why.

Why am I passionate about this?

At 13 years old I told my father that “I will be travelling around the USA as soon as I graduate college." It took 10 days to prepare but prepare and depart I did. I worked my way around the USA for 6 months and on the way home I told my Dad, “Next is Europe.” A year later I traveled with the son of the richest man in the world and the adventures we had driving 19,865 miles through 12 European countries for 10 weeks were both mind-blowing and life-changing. My passion for traveling and life shows throughout my book, and I assure you that you'll enjoy travelling along with me. 

Gary's book list on life and it's changes – the what, where, and why

Gary Orleck Why Gary loves this book

This book was inspirational in making me want to write my own story in order to look into my life-changing adventure, which changed me as a person and gave me a new awareness about myself. I am sure the author would be delighted that his words affected my life that way.

Isn't that why we as authors slave to do our work in order to be heard and change the reader's thinking about life and what it means to them? Well, this author accomplished that and I assure you it will have a similar effect on you if you read it.

Simply put, this may well change your perspective of your own life. 

By John Strelecky ,

Why should I read it?

2 authors picked The Cafe on the Edge of the World as one of their favorite books, and they share why you should read it.

What is this book about?

Gifted by millions to those they love. The simple yet profoundly life changing story for anyone struggling to find their place in life. Seven time winner- Bestseller of the Year.

In a small cafe at a location so remote it stands in the middle of the middle of nowhere, a visitor finds three unusual questions on the back of a menu.

Why are you here?

Do you fear death?

Are you fulfilled?

With this food for thought and the guidance of three people at the cafe, the visitor embarks on a journey of self-discovery. Along the way discovering a new…


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Book cover of Oaky With a Hint of Murder

Oaky With a Hint of Murder by Dawn Brotherton,

Aury and Scott travel to the Finger Lakes in New York’s wine country to get to the bottom of the mysterious happenings at the Songscape Winery. Disturbed furniture and curious noises are one thing, but when a customer winds up dead, it’s time to dig into the details and see…

Book cover of An American Traveler: True Tales of Adventure, Travel, and Sport

Gary Orleck Author Of Travels With Maurice: An Outrageous Adventure in Europe, 1968

From my list on life and it's changes – the what, where, and why.

Why am I passionate about this?

At 13 years old I told my father that “I will be travelling around the USA as soon as I graduate college." It took 10 days to prepare but prepare and depart I did. I worked my way around the USA for 6 months and on the way home I told my Dad, “Next is Europe.” A year later I traveled with the son of the richest man in the world and the adventures we had driving 19,865 miles through 12 European countries for 10 weeks were both mind-blowing and life-changing. My passion for traveling and life shows throughout my book, and I assure you that you'll enjoy travelling along with me. 

Gary's book list on life and it's changes – the what, where, and why

Gary Orleck Why Gary loves this book

This is a collection of a dozen essays allowing us to feel the fun, the drama, the craziness of travel, and the effect it can have on both our personalities and views after the journey. In other words, this book teaches us to feel these stories, which show us the more you risk the more rewards you will gain from your travel adventures.

It also reminds us to worry or at least be concerned for whom you are traveling with. After reading this, I believe it is not what we accomplish by traveling but what we take away from traveling.

By Randy Wayne White ,

Why should I read it?

1 author picked An American Traveler as one of their favorite books, and they share why you should read it.

What is this book about?

A scintillating new collection from one of America's premier travel writers.


Book cover of Starter Dog: My Path to Joy, Belonging and Loving This World

Martha W. Murphy Author Of CRU Oyster Bar Nantucket Cookbook: Savoring Four Seasons of the Good Life

From my list on the eclectic reader of nonfiction.

Why am I passionate about this?

I’m a narrative nonfiction writer interested in a broad range of topics, including but not limited to: food and the people who bring it to us; travel and life in faraway places; human health and the role of medicine; memoir as one person’s story yet illustrative of the human spirit; and the unique and remarkable role dogs play in our lives. I am the same kind of reader: I read across a range of topics, mostly nonfiction. The bookshelves in my house and the record of titles I’ve checked out from my local library show an eclectic taste, as do the books I’m recommending here. I hope you’ll enjoy them!

Martha's book list on the eclectic reader of nonfiction

Martha W. Murphy Why Martha loves this book

When Rona Maynard’s husband of nearly 50 years said one evening, “Let’s get a dog,” she was inclined to say, “Let’s not.” Indeed, as an online review of Starter Dog notes, this book is “an irresistible tale of reluctant dog ownership full of heart, humor, and wisdom.”

It’s all that and more. And so, as a person who loves to read books about dogs, I was delighted to come across this one.

Maynard writes beautifully (no surprise she was Editor In Chief at Chatelaine for 20 years), hence it is not only the captivating tale itself but also her way with words that makes this such a moving collection of 36 short chapters. You’ll smile, laugh out loud, and weep (I did), and be grateful for Maynard’s gift to readers.

By Rona Maynard ,

Why should I read it?

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

What is this book about?

An irresistible tale of reluctant dog ownership full of heart, humor, and wisdom

Rona Maynard wants to love her life again. Stuck in the what-next doldrums after quitting a big job, she needs a new bridge to the world. So, well into their married life, she lets her husband talk her into their first dog, a rescue mutt named Casey. Rona frets about shedding, lost travel opportunities, and arguments about walking duty. She doubts she can love a dog. But when Casey romps through her door, Rona falls hard. Over time he gives her what no human could ― a…


Book cover of The Gentle Tamers: Women of the Old Wild West

Jan Mackell Collins Author Of Behind Brothel Doors: The Business of Prostitution in Kansas, Nebraska, and Oklahoma (1860–1940)

From my list on historical prostitution.

Why am I passionate about this?

Having grown up with an older generation—my great-grandparents, great-great aunts and uncles, and a godmother, all who were born between 1877 and 1900—I learned to appreciate how they lived and what they went through. As a child, I found a hand-written poem about a brothel queen who caused a gunfight between her paramour and a stranger. Then, in college, I met a wonderful old man who told me stories about the former red-light district right in my own neighborhood. Once I learned the often tragic, but also successful stories of these ladies, I decided to be their voice and remind America how important they were to our history.

Jan's book list on historical prostitution

Jan Mackell Collins Why Jan loves this book

First published in 1958, this is one of the first books to pay respect and present the truth about the struggles western women faced. Mr. Brown was very thorough in covering women’s roles in the west, from homesteaders and wives, to women kidnapped by Natives, to actresses and prostitutes. He also used primary sources, not the internet, to conduct his research. 

By Dee Brown ,

Why should I read it?

1 author picked The Gentle Tamers as one of their favorite books, and they share why you should read it.

What is this book about?

All aspects of western feminine life, which include a good deal about the western male, are covered in this lively, informal but soundly factual account of the women who built the West. Among those whose stories are included are Elizabeth Custer; Lola Montez, Ann Eliza Young, Josephine Meeker, Carry Nation, Esther Morris, and Virginia Reed.


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Book cover of December on 5C4

December on 5C4 by Adam Strassberg,

Magical realism meets the magic of Christmas in this mix of Jewish, New Testament, and Santa stories–all reenacted in an urban psychiatric hospital!

On locked ward 5C4, Josh, a patient with many similarities to Jesus, is hospitalized concurrently with Nick, a patient with many similarities to Santa. The two argue…

Book cover of Staking Her Claim: Women Homesteading the West

Marsali Taylor Author Of Women's Suffrage in Shetland

From my list on real women who refused to know their place.

Why am I passionate about this?

I’m Marsali Taylor, a retired teacher of English, French and Drama. I’ve always been interested in women’s history—not queens and countesses, but what life was like for ordinary people like me. A chance to research women’s suffrage in the Scottish National Library got me started reading these women’s stories in their own words—and what stories they were, from the first women graduates to the war workers. Women’s Suffrage in Shetland took two years of fascinating research, and I hope it’s the foundation for more work by other researchers, both here in Shetland and in other communities whose women fought for the vote.

Marsali's book list on real women who refused to know their place

Marsali Taylor Why Marsali loves this book

These women did know their place – they’d measured it out, filled in the claim forms, assembled their tiny wood shack cabin or turf –roofed dugout, sewn their corn and dug their vegetable patch. The usual picture of pioneer women is as the mother of the family, but a staggering 12% of those Wild West pioneering homesteaders were single women or widows, and this is the story of over twenty of them. After introductory chapters, it’s told in their voices, through magazine articles, letters back home and memoirs written later. We learn about how they set out on their adventure, the reality of farming and how they coped, and their triumph as they won their claim. Fascinating.

By Marcia Hensley ,

Why should I read it?

1 author picked Staking Her Claim as one of their favorite books, and they share why you should read it.

What is this book about?

Instead of talking about the rights of women, these frontier women grabbed the opportunity to become landowners by homesteading in the still wild west of the early 1900s. Here they tell their stories in their own words-through letters and articles of the time-of adventure, independence, foolhardiness, failure, and freedom.


Book cover of Skyfaring: A Journey with a Pilot
Book cover of Unbroken
Book cover of A Walk in the Woods: Rediscovering America on the Appalachian Trail

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5 book lists we think you will like!

Interested in the American West, homesteading, and the Oregon Trail?

The American West 145 books
Homesteading 42 books