8 Books About the History (and Digital Legacy) of the Oregon Trail

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Alice Nuttall

Senior Contributor

Alice Nuttall (she/her) is a writer, pet-wrangler and D&D nerd. Her reading has got so out of control that she had to take a job at her local library to avoid bankrupting herself on books - unfortunately, this has just resulted in her TBR pile growing until it resembles Everest. Alice's webcomic, writing and everything else can be found at

From the 1830s to the late 1860s, the Oregon Trail was one of the major routes for anyone wanting to travel west across the United States — and it certainly became the most famous, leading to many books about the Oregon Trail being written.

On the Oregon Trail, several towns developed specifically to serve travellers along the route, many of which remain today. Despite being a well-established trail, travelled by nearly half a million people during its 30-year heyday, the Oregon Trial was difficult and challenging, with dangers in the form of disease or natural disasters along the way. The Oregon Trail’s time ended with the coming of the railways, which made long journeys across the country much quicker and safer for everyone involved.

Despite only lasting for around 30 years, the Oregon Trail has had a huge impact on pop culture, most notably in the famous and much-loved 1971 game. The educational computer game allowed kids to play as a wagon leader guiding a party along the trail, making the hard decisions along the way that, depending on the choices you make, can lead to success or disaster. The game has kept its cult popularity right through until the present day, spawning sequels, remakes and parodies (including a zombie apocalypse version, Organ Trail). Both the historical event and the game feature in a number of books — here are some of the best reads following the wagon trail.

The Historical Trail

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The Oregon Trail by Francis Parkman Jr

A first-hand account written by an Oregon Trail traveller, The Oregon Trail is a crucial resource for anyone who wants to gain an insight into what this long and arduous journey was like for those who attempted it. Written in 1846, Parkman Jr’s account reflects the attitudes and particularly the racism of the time, so should be read through a critical lens.

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The Water Seeker by Kimberly Willis Holt

This middle grade book about the Oregon Trail follows Amos, a young boy who has the gift of dowsing — a supernatural ability to water. A great read for kids learning about this period of history, The Water Seeker blends fact and fiction to create a compelling adventure.

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Under a Painted Sky by Stacey Lee

In this historical fiction, Samantha, a Chinese American girl, and Annamae, a formerly enslaved African American girl, disguise themselves as boys in order to travel on the Oregon Trail and make their way to California. As well as surviving the harsh landscape, the two girls learn about friendship and how to work together to achieve their goals.

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Women’s Diaries of the Westward Journey by Lillian Schlissel

Women’s historical perspectives are often sidelined, if they’re ever acknowledged at all. A lack of access to education or publishing meant that women of the past were less likely to be able to share their writings in the same formal or commercial way as their male counterparts. However, many women recorded their experiences in letters or diaries, and this collection of writings by women who travelled the Oregon Trail gives important context to this historical period.

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Wagons Ho! by George Hallowell, Joan Holub, and Lynne Avril

With this cute picture book, young children can learn about the Oregon Trail and also grapple with major modern-day life events. In this story, two girls, one in the 19th century and one in the present day, travel from Missouri to their new homes in Oregon. Although they deal with very different situations along the way, they also have some new challenges in common.

Our Favourite Historical Game

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Tomorrow and Tomorrow and Tomorrow by Gabrielle Zevin

The highly-acclaimed Tomorrow and Tomorrow and Tomorrow follows two best friends (who sometimes hate each other), Sam and Sadie, who first bond in a hospital over their shared love of games — including the classic The Oregon Trail. As the two grow up and become professional game developers, they frequently come together and are pushed apart by their interest in games, with The Oregon Trail often providing inspiration.

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And Then You Die of Dysentery: Lessons on Adulting from the Oregon Trail by Lauren Reeves and Jude Buffum

Anyone who has played The Oregon Trail — and even those who haven’t — knows the phrase “You have died of dysentery,” which is so memorable that it has become a meme. This darkly comic book about everyday life draws on the game as a framework, using it to give advice on the modern world.

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White Magic: Essays by Elissa Washuta

In this collection of essays, Elissa Washuta writes about her life and experiences as a Native American woman, and her journey back to her cultural roots following disconnect, abuse and trauma. Washuta writes about PTSD and colonisation, but also discusses examples of pop culture that have impacted her life, including The Oregon Trail.

While the impact of both the historical Oregon Trail and its computer game counterpart are undeniable, we must note that the voices of Indigenous people are frequently overlooked when it comes to studying the history of the Old West, or the way this period is represented in pop culture. Books like The Heartbeat of Wounded Knee by Ojibwe author David Treuer are an essential read for anyone who wants to gain a full understanding of the historical context of this period of American history. For more recommendations, try Children’s Books By Native American and Indigenous Authors. If you’re interested in learning more about the Old West, look at our list of 100 Must-Read Books of the American West.