100 Books Like The Oregon Trail

I have re-read this classic several times since I was a child.

The abridged version I read in 4th grade. RLS himself said, “The characters took the bit in their teeth; all at once they became detached from the flat paper, they turned their backs on me and walked off bodily…”

Not long after being introduced to Alan Breck Stewart, we hear him exclaim, in a ship’s cabin filled with the blood of villains he has shed, “Ah Davy, am I no’ a bonnie fighter!” How often, as a lad, I imagined myself taking on that crew with my broadsword!

Young David Balfour, in his quest to get back his inheritance, learns from Alan and his complex character that the Jacobite cause in Scotland is not clearly a matter of right and wrong. Did Alan kill “the Red Fox”? This is debated among Highlanders to this day! 

Originally published in 1932, this remains one of the most accessible and thought-provoking books ever written about the American West. Webb’s work rises to the level of literature, especially when describing early encounters by white Americans with the landscape and native people they met west of the 98th meridian. Few writers have captured so vividly the expansion of America from the humid and forested east to the arid west of the Great Plains. Some of Webb’s conclusions may feel a little dated, but this remains a very compelling and rewarding book.

A thrilling if bumpy ride through 1846, as DeVoto tracks multiple stories of Americans who headed west at the start of the great migration. Like Webb’s Great Plains, this book — published in 1942 — is a little dated in places, but DeVoto’s vivid descriptions and strong opinions make it highly enjoyable. The general subject is the “period when the manifold possibilities of chance were shaped to converge into the inevitable,” writes DeVoto. More plainly, the book is about "some people who went west in 1846." Many of them died on the way. Some found fortune. Altogether, they left behind extraordinary history.

Posthumously published in 1970 by the University of Illinois Press, this is a must-have for anyone interested in the early years of the western migration. Unruh — who died young shortly after completing the manuscript —performs the essential task of assembling credible data about emigrants and Native Americans, and — most importantly — about their encounters with each other. Popular myths and Hollywood movies notwithstanding, Unruh makes clear that Native Americans seldom caused emigrants much harm. Indeed, emigrants of the 1840s were more likely to shoot themselves and each other by accident than require a gun for self-defense.

No book captures more clearly and compellingly the horrific, inspiring, and vital histories and stories of Native Americans than Brown’s.

I love the ways that Brown offers a profoundly new perspective on the American West, on the foundational myths that too often limit the way we see ourselves and the realities with which we must grapple instead, and on Indigenous communities as an essential part of the American story at every stage.

Revisionist Westerns are one of my very favorite genres, and this is the best one I know.  

Peter is on his way home from school and discovers a crooked laneway. Soon he looks through the bay window of a junk shop and is ‘drawn’ towards one item inside: a little ship. There is a strange conversation between Peter and the owner of the shop who says, "All the money in the world wouldn’t have bought this ship once [...]. It would cost all the money you have in the world and a bit over!" The man in the shop sells it to Peter.

Along the beach on the way home the ship turns into a real ship with sails. The book is not only about the many adventures with his brothers and sisters involving time travel to many lands but has an overarching plot that one day Peter will have to return the ship where he bought it. Only then will he discover about the ship and… show more.

In being faithful to the ‘first’ books I ever read The Ship That Flew and The Adventures of Henry Penn. Henry Penn is a Penguin and daydreamer. He wants to be a poet. Some of the story involves his creative life writing/reciting from his ‘secret’ little book the “Lays of Ancient Penland.” The close of the story recounts an episode after the Kipper War when there is a celebration concert and Henry performs his first poem!

The town’s people (Penguins) dominate the story. The Kipper War (is a funny episode) against the Pirates to recover the stolen hoard of fish belonging to the Penguins. Important in all of the books chosen are the illustrations, for instance, the illustration of Henry in school at the back of the class ‘caught’ by the teacher staring out the high windows.

Lang’s story telling is compelling opening up for the reader the timeless characters of Cinderella, Little Red Riding Hood, Hansel & Gretel, Jack the Giant Killer, Jonathan Swift’s “A Voyage to Lilliput” from Gulliver’s Travels, Aladdin, Sleeping Beauty, Rumpelstilzkin, Why the Sea is Salt, Goldilocks, Blue Beard, Snow White and many others. 

My sister and brother (older than I) used to read aloud from, not only The Blue Fairy Book but the Red Book and the Green Book. These stories were the first I’d heard, and were so real I believed the characters would be present in my life. Grimm’s Tales ‘told’ by Lang becomes an exciting guidebook for a young person growing up. This aspect was ‘proven’ to me by the co-existence of these characters as archetypes in terms of life events and situations. My conviction is that the storyline, characters, and the progression of events in… show more.

Horse stealing was more than theft of valuable and essential property. Matthew Luckett explains that on the Great Plains horse stealing “destabilized communities, institutions, nations, diplomatic relations, and cross-cultural exchange.” Luckett challenges many popular notions about horse thieves (for starters, they were not hung).  There were different kinds of horse theft and horse thieves. Don’t be misled by “Nebraska” in the title—this book shows that horse stealing had regional and national repercussions.   Luckett is an engaging writer, and this book is extremely readable and filled with compelling stories. I particularly recommend the chapter “The Horse Wars” about the role of horses in the war the U.S. Army waged against the Indians. 

This dual-biography has the best description of Custer’s death ever written. Of course, no one knows exactly what happened, and that sense of mystery is one of the reasons it has become part of American lore. But master historian Stephen Ambrose uses the available evidence to speculate in a few beautifully written paragraphs what brought Custer to his legendary defeat and how he might have reacted to it in his last moments. The comparative stories of Custer and Crazy Horse leading to the battle is a fast-paced tale that will make you keep turning pages, forgetting you know how it will end. But the book is more than fine writing. The dual-biography format is the perfect vehicle for Ambrose to explain the clash of cultures that led to tragic conflict.