* BeamMeUpScotty: The line "You have died of dysentery" never literally appears in the original version of ''The Oregon Trail''. The actual phrasing only mentions the disease in the third-person voice: "[[HelloInsertNameHere [Character name the player entered]]] has dysentery."
* KeepCirculatingTheTapes:
** A well-known meme from Oregon Trail exists ''because'' of people 'circulating tapes'. Why does everyone remember "[[GraveHumor here lies andy; peperony and chease]]"? Because [[http://www.mentalfloss.com/blogs/archives/25430 a player put that tombstone into a copy of the game that was widely pirated, and in the heyday of emulation, found its way into almost all Apple II disk image archives online.]] (The "pepperoni and cheese" joke itself is almost certainly a reference to [[https://youtu.be/vKspf06XuaQ this '90s Tombstone Pizza ad.]])
** The [=iPhone=] and [=iPad=] ports are becoming subject to this. Firstly, it works best on [=iOS 5=] or older, and [=iOS 11=] will not run it because it's a 32-bit app, so you'll need access to an OG [=iPad=] or a considerably old [=iPhone=] to run it. Then because it's no longer available in the app store, you need to have already backed up the app on an old pre-version-11 version of iTunes (if you bought it beforehand) or get it from somewhere and jailbreak your device to install it. And to top it all off, due to the additional {{freemium}} functionality (on top of the fact that this is a ''paid app'', mind you), it needs a connection to Gameloft's servers, which no longer exist, and the error condition of the game causes it to ''not run at all'' if it can't reach the servers. Ouch.
* ItsBeenDone: When Target put out a handheld version of the game in 2018, people were crying out for a port of ''Oregon Trail'' for [=iOS=] and Android. That actually happened in 2011 (see Porting Disaster entry in YMMV), but then Gameloft mismanaged the franchise and [[ScrewedByTheNetwork screwed the game over]]...[[note]]Speculation abound that Gameloft only agreed to porting the game because they wanted the license to the franchise to create a "''VideoGame/FarmVille'' clone" based around Oregon Trail. This is mostly supported by the fact that said ''[=FarmVille=]'' clone is still going strong while the actual game ports had been retired several years ago.[[/note]]
* LetsPlay: A very popular target for this, especially the second edition of the game. It's believed to be the first screenshot LP done on Website/SomethingAwful.
* MultiDiscWork: The 5¼" DOS version has two disks.
* PortOverdosed: An extremely widespread game, ending up on virtually every computer platform from the mid-80s to present.
* ReferencedBy:
** ''[[WebAnimation/DorklyOriginals Dorkly Bits]]'':
*** "In Power Up Mix-up (Part 1)", [[ExactlyWhatItSaysOnTheTin as a result of video games getting their power-ups mixed-up]], the [[VideoGame/{{Doom}} BFG9000]] is delivered to ''The Oregon Trail'', allowing the player to kill every single animal when they shoot them.
*** In "If Video Games Had Impossible Mode", the player shoots at animals, when suddenly, a monster from ''VideoGame/{{Doom}}'' appears out of nowhere. Due to the monster's immunity to bullets, the player cannot kill it and ends up getting killed by it instead.
*** In "Power-Up Mix-up (Part 5)", twenty [[VideoGame/FTLFasterThanLight Faster Than Light Drives]] are delivered to ''The Oregon Trail''. The player buys all twenty of them, allowing their wagon to reach Oregon quickly and easily.
** An episode of ''WesternAnimation/LooneyTunesCartoons'' is titled "Oregon Fail". In this episode, Yosemite Sam tries to get to Oregon before the other settlers by sabotaging their chances. He ends up getting his comeuppance when his open wagon breaks down near Bugs Bunny's burrow.
* ScienceMarchesOn: Inverted, actually, in ''Oregon Trail II'' and its sequels. While you're limited to nineteenth-century medicines, the medical advice from your guidebook and other characters is unrealistically accurate for the period. For example, cholera being airborne was the overwhelming medical consensus of the time. The disease being waterborne was first proposed by John Snow in 1854[[note]]Apparently he did ''not'' [[Series/GameOfThrones know]] [[MemeticMutation nothing]][[/note]], and his view was extremely controversial for a while. The game, however, acts like it's already an established fact that cholera is waterborne. Also, bloodletting was a be-all-end-all treatment during the period in which the game takes place, but it's never offered as an option or even mentioned.
** Played straight in ''Oregon Trail II'' with alkali sickness. Shortly after 1860 it was discovered that what was then called "alkali sickness" had nothing to do with alkali but ingesting white snakeroot poison. The game treats it as if it was actually alkali.
* SleeperHit: According to [[https://youtu.be/LJVdlivdKak this video]] "Five Unbelievably Massive Franchises You've Probably Never Heard Of", the various editions of ''The Oregon Trail'' have sold a collective 65 million copies, which is a similar amount to ''VideoGame/{{Battlefield}}'' and ''Franchise/{{Halo}}''.
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