70 free Oregon Trail trivia questions with answers — history quiz, new questions added Aug 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 70 questions with answers and explanations. Play the quiz
Q 01Three student teachers from which Minnesota school wrote the original Oregon Trail in 1971?
Carleton
Don Rawitsch, Bill Heinemann and Paul Dillenberger built it in about two weeks for an eighth-grade history unit, then deleted it from the school district's computer when the semester ended.
Q 02In what year did the very first version of The Oregon Trail debut in a Minneapolis junior-high classroom?
1971
It ran on an HP 2100 minicomputer that students reached through a single teleprinter, so the game had no graphics at all.
Q 03In the original teleprinter version, what word did players have to type to fire their gun while hunting?
BANG
Later versions randomised the word between BANG and POW, and typing it faster earned more food; a misspelling meant the shot did nothing.
Q 04Which four-letter organisation produced and distributed The Oregon Trail from 1975?
MECC
The Minnesota Educational Computing Consortium was state-funded and gave the game to Minnesota schools for free while selling it elsewhere.
Q 05Which future music superstar was among the Minneapolis students who play-tested the first version?
Prince
Heinemann and Dillenberger let students at Bryant Junior High try it, and the kids stayed late at school for another turn.
Q 06In the 1985 game, the wagon party sets out from which town on the Missouri River?
Independence
The real trail had many jumping-off points, but the game picked the classic one, with the journey set in 1848.
Q 07Where does the journey end in the 1985 game?
Willamette Valley
The 1971 original had aimed for Oregon City instead; both are in the same fertile valley west of the Cascades.
Q 08Which of these is one of the three professions a player can choose at the start of the 1985 game?
Carpenter
Banker, carpenter and farmer doubled as difficulty levels, each starting with a different amount of cash.
Q 09In the 1985 game, where do you buy oxen, food, clothing, ammunition and spare parts before setting off?
Matt's General Store
Prices for the same supplies rise the further along the trail you get, so stocking up in town pays off.
Q 10Which of these is one of the ways to cross a river in the 1985 game?
Caulk the wagon and float it across
Fording, caulking and (at some crossings) paying for a ferry were the choices, and the odds depended on the river's depth and the weather.
Q 11On the last leg of The Oregon Trail (1985), players can pay a toll or raft down which river?
Columbia
The rafting sequence was nearly cut for time and was rebuilt at the last minute as a simple rock-dodging game in Applesoft BASIC.
Q 12What is the maximum food weight you can carry back to the wagon in Oregon Trail's 1985 hunting minigame?
100 pounds
The cap was a deliberate history lesson: a real hunter could only haul so much meat back before it spoiled.
Q 13Who was the lead designer of the 1985 graphical remake of The Oregon Trail?
R. Philip Bouchard
Bouchard's guiding rule was that the fun should come from immersing the player in an accurate experience, not from lecturing them about history.
Q 21What is the name of the 2012 parody game that swapped the pioneers for survivors of a zombie apocalypse?
Organ Trail
It was made by a studio called The Men Who Wear Many Hats and released for browsers, iOS and Android.
Q 22The 2021 remake of The Oregon Trail, developed by Gameloft, launched first on which subscription service?
Apple Arcade
Its creative director consulted Native American scholars to remove stereotypes, and the game acknowledges that for Native nations colonisation was an invasion, not an adventure.
Q 23In the 1975 mainframe version, the trip was played as roughly how many rounds, each standing for two weeks?
12
Q 14Which grim message from the game became a popular T-shirt slogan?
You have died of dysentery
The 1985 team removed the original's medicine-and-doctor system as inaccurate and replaced it with several distinct diseases.
Q 15In which year was The Oregon Trail inducted into the World Video Game Hall of Fame?
2016
It was the first educational game to get in, and stayed the only one until Where in the World Is Carmen Sandiego? joined in 2021.
Q 16Across all its versions, roughly how many copies of The Oregon Trail had been sold by 2011?
65 million
For years the game came bundled with school computers, which is how so many children ended up playing it without anyone buying it for them.
Q 17Which company bought MECC in 1995 and published the next few games in the series?
SoftKey
MECC had only become a publicly traded company the year before; it was shut down entirely in 1999.
Q 18Which educational game joined The Oregon Trail in The Strong museum's hall of fame in 2021?
Where in the World Is Carmen Sandiego?
Both games date from 1985 and both defined the edutainment shelf of American classrooms.
Q 19When Time magazine ranked the 50 best video games of all time in 2016, where did The Oregon Trail place?
9th
Time credited it with introducing several generations to video games in the first place.
Q 20Which of these was a real MECC spin-off game in the same series?
The Amazon Trail
The Yukon Trail, Africa Trail and MayaQuest: The Mystery Trail rounded out the family.
Rawitsch recalibrated the odds of storms, breakdowns and other events for that release using real diaries from the trail.
Q 24In the 1985 hunting minigame, how did the game show that an animal had been shot?
It flipped upside down
That was a placeholder because the proper death graphics weren't finished for playtesting, but the children found it so funny the team kept it.
Q 25StarKid Productions turned the game into a parody stage musical in 2014. What was it called?
The Trail to Oregon!
It premiered in Chicago and was later posted in full on YouTube, like StarKid's earlier hit A Very Potter Musical.
Q 26The famous 1985 graphical version of The Oregon Trail was first released for which computer?
Apple II
MS-DOS, Mac and Windows ports followed between 1990 and 1993, and a Basic Fun handheld version arrived in 2018.
Q 27In which programming language was the 1971 original written?
BASIC
The whole thing was about 800 lines, which the trio printed out before deleting it, allowing Rawitsch to retype it for MECC three years later.
Q 28Don Rawitsch published the game's full source code in the May–June 1978 issue of which magazine?
Creative Computing
He included some of the historical data he had used to tune the odds of disasters along the trail.
Q 29In what year was Oregon Trail II released?
1995
A 25th Anniversary Limited Edition came in a commemorative wooden box with a strategy guide and a certificate of authenticity.
Q 30When MECC went public in 1994, The Oregon Trail made up roughly what share of annual revenue?
One third
Nine years after release it was still the company's flagship product.