* 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.
* 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."
* HellIsThatNoise: DUN DUN!
* InferredHolocaust: The first game ends when you [[InstantWinCondition reach the Willamette Valley]]. You might be down to two party members, two bullets, and one ox when you get there. In January. Good luck surviving til spring.
** Pioneers had been traveling west to Oregon for years before the 1848 start date in the game - presumably you'd be able to find a settlement in the area where your party could shelter until the weather gets better. Plus, this is Oregon west of the mountains, not Alaska or Montana - it's a mild place with a lot of rain all year round.
* MemeticMutation: You have died of dysentery.
** However, you were only able to carry 100 pounds back to the wagon.
** [[GraveHumor 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''.
*** Needs more bacon!
** From 4chan threads:
*** YOU WILL FORD THAT SHIT!!! Essentially, any river you come across no matter what size or depth you must [[RatedMForManly be a man]] and ford it.
* 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[=/=]ScareChord: ''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 [[UpdatedRerelease 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...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 {{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 whopping 330MB download and expands to a whopping 1.2GB upon decompression.
* 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.