Oregon Trail Trivia
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61 free Oregon Trail trivia questions with answers — history quiz, new questions added Oct 2026.
This Oregon Trail trivia quiz covers both things people mean by the name: the real 2,170-mile wagon route that carried around 400,000 emigrants from the Missouri River to the Pacific Northwest, and the classroom computer game that taught a couple of generations to fear dysentery. Expect questions on Independence, Missouri, Fort Kearny and Fort Laramie, Chimney Rock and Independence Rock, South Pass, the Barlow Road, oxen versus mules, and the diseases and accidents that actually killed people on the trail. The game half runs from the 1971 teleprinter original written by three Carleton College student teachers, through the 1985 Apple II classic (Matt's General Store, caulking the wagon, the hunting minigame) to the sequels, parodies and the 2021 remake. Roughly a third of the questions are easy for anyone who played the game in school, a third are medium, and the rest will test people who have read the trail diaries. Every answer has been checked against an encyclopaedic or primary source, and each question links to the page that confirms it.
30 of 61 questions with answers and explanations. Play the quiz
Q 01Student teachers from which Minnesota college wrote the original Oregon Trail?
Carleton
Carleton College seniors Don Rawitsch, Bill Heinemann and Paul Dillenberger shared a Minneapolis apartment while student teaching, and designed and coded the game in about two weeks.
Q 02The first Oregon Trail was written in 1971 for a junior-high class in which subject?
History
History: student teacher Don Rawitsch was drawing a board game for his unit on westward expansion when his roommates, two student maths teachers who could program, talked him into a computer version.
Q 03In the original teleprinter version of The Oregon Trail, what word did players type as fast as they could to hunt?
BANG
BANG had to be typed quickly and spelled correctly: the faster the entry, the more meat, and a typo meant nothing at all, so classes put their best typist on hunting duty.
Q 04Which Minnesota organisation produced and distributed The Oregon Trail from 1975?
MECC
MECC, the Minnesota Educational Computing Consortium, was a state agency; once the game went onto its timeshare system in 1975 it became the most popular program schools dialled into.
Q 05In The Oregon Trail (1985), the wagon party sets out from which town on the Missouri River?
Independence
Independence, Missouri is the only place to set out from, but the 1985 game added a choice of departure month: leave too early and there is no grass for the animals, too late and snow closes the mountains.
Q 06Where does the journey end in The Oregon Trail (1985)?
Willamette Valley
The Willamette Valley lay beyond the Cascade Mountains, which is why the game's last decision is between a toll road over them and a raft ride down a river full of rocks.
Q 07In The Oregon Trail (1985), what did choosing to be a banker, a carpenter or a farmer decide?
Your starting money
Your starting money was all the choice changed: the designer wanted easy, medium and hard levels without building three games, and a richer start earns fewer points at the end.
Q 08Where does the 1985 Oregon Trail game have you buy food, clothing and ammunition before leaving?
Matt's General Store
Matt's General Store at the start of the 1985 game sells the supplies; the same goods cost more at the forts along the trail, so stocking up before leaving pays off.
Q 09How can you cross a river in the 1985 Oregon Trail game?
Caulk the wagon and float it across
Players could ford the river, caulk the wagon and float it across, or at some crossings pay for a ferry; the odds depended on the river's depth and the weather.
Q 10On the last leg of The Oregon Trail (1985), players can pay a toll or raft down which river?
Columbia
At The Dalles the player chooses between rafting down the Columbia River, dodging rocks in a simple action minigame, or paying to take the Barlow Toll Road around it.
Q 11What is the maximum food weight you can carry back to the wagon in Oregon Trail's 1985 hunting minigame?
100 pounds
However much you shoot, the 1985 game lets you carry only 100 pounds back to the wagon; its designer set the cap so children would think about waste.
Q 12What did the 1985 Oregon Trail game save to disk for later players to find?
A tombstone with an epitaph
A tombstone with an epitaph: when the whole party died, the leader got a gravestone the player could inscribe, and the game stored it on the disk for the next player to pass.
Q 13Which grim message from The Oregon Trail became a popular T-shirt slogan?
You have died of dysentery
Q 21In The Oregon Trail's 1985 hunting minigame, how did the game show that an animal had been shot?
It flipped upside down
Hit an animal and it flipped upside down: the team used that as a stand-in until proper death graphics were ready, but playtesting children loved it, so it stayed.
Q 22What did StarKid Productions call its 2014 stage musical parodying The Oregon Trail?
The Trail to Oregon!
The Trail to Oregon! has the audience name the family at the start and vote on which member dies at the end; StarKid later posted the whole show on YouTube.
Q 23The famous 1985 graphical version of The Oregon Trail was first released for which computer?
Apple II
'You have died of dysentery' became a meme and a T-shirt staple; the 1985 version introduced several named illnesses, dysentery among them, in place of generic sickness.
Q 14Which hit of 2000 entered the World Video Game Hall of Fame alongside The Oregon Trail?
The Sims
The Sims entered the hall in 2016 alongside The Oregon Trail, which the judges honoured as a single game across every version, from mainframe to smartphone.
Q 15Across all its versions, roughly how many copies of The Oregon Trail had been sold by 2011?
65 million
About 65 million copies had been sold by 2011, a striking total for a game first handed out free to Minnesota schools.
Q 16Which toy giant bought The Oregon Trail's owner, The Learning Company, in 1999?
Mattel
Mattel bought The Learning Company in 1999; that firm, once called SoftKey, had already swallowed the game's Minnesota publisher, whose offices closed the same year.
Q 17Which educational game followed The Oregon Trail into The Strong museum's hall of fame in 2021?
Where in the World Is Carmen Sandiego?
Where in the World Is Carmen Sandiego? (1985) shipped with a copy of The World Almanac, which players combed for clues to the thief's next stop; it joined the hall in 2021.
Q 18Which of these was a real spin-off in the Oregon Trail series?
The Amazon Trail
The Amazon Trail (1993) sends players up the river by canoe to carry cinchona, a malaria remedy, to the Inca king; The Yukon Trail and Africa Trail were sister titles.
Q 19Which parody game swaps The Oregon Trail's pioneers for survivors of a zombie apocalypse?
Organ Trail
Organ Trail began as a free browser game from The Men Who Wear Many Hats; its popularity led to a Kickstarter-funded Director's Cut for iOS and Android in 2012.
Q 20The 2021 remake of The Oregon Trail, developed by Gameloft, launched first on which subscription service?
Apple Arcade
Gameloft's remake debuted on Apple Arcade in 2021 and reached PC and consoles the next year; its creative director consulted Native American scholars to strip out stereotypes.
The 1985 version was written for the Apple II, the computer its publisher had been buying in bulk and reselling to schools; MS-DOS, Mac and Windows ports followed in 1990–1993.
Q 24In which programming language was the original Oregon Trail written?
BASIC
The original was written in BASIC on the Minneapolis schools' timesharing computer; the team kept a paper copy of the code before deleting it, and Rawitsch rebuilt the game from it in 1974.
Q 25How did Don Rawitsch share The Oregon Trail's full program in 1978?
Printed in a magazine
Printed in a magazine: Creative Computing ran the full listing in 1978, with some of the historical data he had used to set the odds of disaster.
Q 26What did Oregon Trail II let players choose for the first time?
Year
Year: the 1985 game always set out in 1848, but Oregon Trail II (1995) offered any year from 1840 to 1860, and the trail changed with the year chosen.
Q 27The 'Oregon Trail Generation' is a nickname for which micro-generation?
Xennials
Xennials, born roughly 1977 to 1983 between Generation X and the millennials, earned the nickname because so many of them played the game on school computers.
Q 28Roughly how long was the Oregon Trail from the Missouri River to Oregon?
About 2,000 miles
About 2,000 miles is the usual round figure (the mapped route is 2,170); wagons needed four to six months, so trains left in spring to beat the mountain snows.
Q 29Which shallow, muddy river did the trail follow across the plains, 'too thin to plow and too thick to drink'?
Platte
The Platte, in the pioneers' joke a mile wide and inches deep, was useless for boats, but its flat valley gave wagons a natural road west with grass and water.
Q 30Which army post, founded in 1848, sold emigrants supplies and carried their mail on the early plains stretch of the trail?
Fort Kearny
Fort Kearny was sited just west of where the feeder trails from the Missouri River towns merged, so the army could guard and resupply the one road they became.