* AccidentalInnuendo: You're fording the river and the water's going too fast. If you don't tie your wagon down, you might lose all of your supplies! [[BoundAndGagged Would you like to use rope and chains?]]
* BigLippedAlligatorMoment: The cartoon segments in the fifth edition.
* GameBreaker: In the second and fifth editions, buy some 10-lb sacks of salt and then go hunting. By doing this, your wagon will fill up with well over 1,000 pounds of salted meat which you can trade for essentials.
* GoodBadBugs: As noted in the KaizoTrap entry on the main page, it's possible to die after winning the game, leading to [[TemporalParadox the hilarious situation]] of you being elected as a city council member, opening a business, or raising money to help Civil War widows despite having died decades earlier. As one [=YouTube=] comment said, "the county board of supervisors elects people 25 years after their death, no wonder they never get anything done."
* MemeticMutation: You have died of dysentery.
** However, you were only able to carry 100 pounds back to the wagon.
** Here lies andy, peperony and chease.
** Sorry, but no one's got ''insert trade item here'' to spare.
** From Something Awful's Let's Plays:
*** Fording every river, including ''the Mississippi'' and ''the Missouri''
*** Needs more bacon!
** Anything regarding to Bacon, due to it being the cheapest form of protein aside from Pemmican
*** Iliza from ''Series/LastComicStanding'' also got into this, mentioning things like how she left with only bacon and said "I don't know, give him bacon" in response to ''every'' possible ailment and situation.
** From Website/FourChan threads:
*** YOU WILL FORD THAT SHIT!!! Essentially, any river you come across no matter what size or depth you must be a man and ford it.
** "You have died from exposure" is a popular reaction image among artists venting about being asked to work for free.
* SugarWiki/MostWonderfulSound: In the Windows/Mac version of the first Oregon Trail, the sound that plays whenever a sick party member recovers or the sound that plays when you find wild fruit.
* NightmareFuel: ''Oregon Trail II'''s DUN DUN! of death.
** In the 2001 version, it will play even during events that don't hamper you, like finding an abandoned storage with helpful items left over.
** Also the weird illness/injury noise. "Peggy Sue has cholera."
** The hill music in ''II'' (and presumably 5) can be rather startling when you abruptly switch from cheerful trail music to dramatic, ominous, loud music.
** Randal Morgan in the third edition. If you talk to him when the wagons are circled, there's a chance he'll start talking about how the "dark ain't natural." He goes on to vaguely, but with obvious terror, describe the "things" living in the dark that are trying to find him, and how he'll fight them with his fists if they ever do. It's more tragic than anything in hindsight, as it's pretty clear he has schizophrenia...but when you're young, it sounds as though {{Eldritch Abomination}}s are stalking the caravan.
* PortingDisaster: The iPad version is a terrible, '''terrible''' mess.
** When you trade or buy an ox, buffalo or cow and try to equip them, the game crashes.
** When you try to post your feat to Website/{{Facebook}} using the game, the game crashes.
** The game has a memory leak problem and the entire game can sometimes slow to a crawl.
** The music can just randomly stop playing.
** And oh, compared to the iPhone version of the game, there has been exactly zero updates. And the iPhone version isn't Universal (read: it doesn't run at native resolution on an iPad). And to rub salt on the wound, the game's a massive 330MB download and expands to a whopping '''1.2GB''' upon decompression.
* ScrappyMechanic:
** In the original version, you can take a limit of 100 pounds of meat while hunting. Downplayed in later versions where you can acquire 200 pounds of meat, sometimes a little more depending on how many party members you have.
** Trading in the first game. It's a crapshoot to get someone who has what you need and the game goes to the next day regardless of the result. Multiple failed attempts will deplete your food supply and cost you some traveling time. At least later games give you the option to haggle.
** Accidental gunshot wounds in the second and fifth editions. They appear randomly after you finish hunting and will sometimes kill you instantly, ending your game even if your other party members are still living. If not, they will severely injure you and leave you to die a slow, painful death. These can even happen without firing a single shot!
*** Similarly, you can also get mauled by a bear or a mountain lion (the latter of which you can't shoot) after hunting, and you'll either get killed instantly or keep taking turns for the worse until you die.
** Averted in the third edition where accidental gunshot wounds are self-imposed. They can only happen if you shoot before the game reloads the gun for you (which takes about a second) and they are ''much'' less lethal.
* TearJerker: In the Windows/Mac version of the first Oregon Trail, whenever a party member dies, it plays an ''extremely'' sad instrumental piece. Oregon Trail Deluxe for DOS's death song (which is instead used when ''all'' of your party members die in the Windows/Mac version) is pretty sad as well. Combine that with the picture that's used in either version and it's hard not to cry.
* ThatOneLevel: The river-riding segment at the end.
* TheyChangedItNowItSucks: A common complaint over a new add-on for the iPhone edition, if you pay real money you can buy in-game money and therefore get a higher score... or not paying more money simply means you get a lower score. Fans weren't amused.
* UncannyValley: The cheaply animated cartoon children in the fifth edition. They're just... unsettling.

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