Video Game / The Oregon Trail

It's 83 miles to Big Blue River. We got a full team of oxen, half a box of bullets, it's 1848, and we're wearing sunglasses. Hit it.

"That's how I learned what it means to be an American. To embrace the pioneer spirit, shoot everything that moves, drown my family in a river, and die of starvation somewhere in the midwest."

—1up.com's July 4th Oregon Trail Retrospective

"LITTLE JOHNNY has died of dysentery."

If you lived in the US and attended school from the late 1980s through the Turn of the Millennium, and your classroom or school library was fortunate enough to have a monolithic, clicking heap of machinery called an Apple ][, chances are you remember a little floppy-disc based game called The Oregon Trail.

If you don't, the premise of this Edutainment Game, designed by three student teachers for their history class, is to lead your family across the American frontier of the mid-19th century to reach the promised land: Oregon. The game was originally created by Don Rawitsch, Bill Heinemann, and Paul Dillenberger, with the first version appearing back in 1971. Rawitch later got hired by the Minnesota Educational Computing Consortium. He used his new position to create an improved version of the game in 1974. It later became available in the organization's time-sharing network, where it could be accessed by schools across Minnesota. Further improvements, updates, sequels, etc, have continued appearing over the decades.

The game would start in Independence, Missouri, where the player could select from professions such as carpenter or doctor, which provided bonuses such as improved health or repairs, before purchasing provisions and heading west. On the long adventure that followed, the player would learn how to manage dwindling supplies, decide whether or not to ford rivers or caulk the wagon and try and float across (paying the ferry was for suckers), manage wagon breakdowns, deal with rattlesnake bites, help rid the West of the buffalo scourge, press SPACE BAR to continue, and lose at least three family members to dysentery. After finally arriving at Oregon, players would abruptly have to steer their wagon down a river, dodging rocks and rapids, before reaching Willamette Valley and the end of the game. There was an option to take a toll road and skip the river-riding segment, but again, that was for suckers.

The game was quite popular among both students and faculty; teachers liked it because of the historical aspect and the brain-building challenge of managing the expedition, while students enjoyed shooting everything between the Mississippi and the West Coast while leaving funny tombstones along the trail as the inevitable dysentery-related casualties accrued.

Because of its success, The Oregon Trail boasts a long series of ports, remakes, and sequels:

• The aforementioned 1971 text-only version of The Oregon Trail
  • 1975 Apple][ port (playable here)
  • 1980 port, with added graphics (playable here)
• The Oregon Trail (1985) — For Apple ][ and first graphical version (playable here)
  • 1990 DOS port with better graphics (playable here)
• The Oregon Trail (Macintosh, 1991; DOS, 1992, with "Deluxe" added; Windows, 1993) — Updated Re-release of 1985 game, complete with GUI (DOS port playable here)
• The Oregon Trail II (1995) — Way more customization features, inventory items, events, and extra destinations
• The Oregon Trail 3rd Edition (1997) — Utilizes Full Motion Video for characters, added fishing and produce gathering minigames, removed choices for years and extra destinations
• The Oregon Trail 4th Edition (1999) — Utilizes Full Motion Video and 3D graphics when exploring locations
• The Oregon Trail 5th Edition (2001) — Added animated cartoon segments
• The Oregon Trail (2009) — Gameloft's Mobile Phone Game remake
• The Oregon Trail: American Settler (2011) — Gameloft's mobile city building game taking place after the 2009 game
• The Oregon Trail (2011) — For Wii and uses full 3D engine
• The Oregon Trail (2021) — Another remake by Gameloft for Apple Arcade with a later 2022 port to PC and Nintendo Switch, notable for including Indigenous travelers for the first time, with Gameloft going out of their way to make sure the representation is as accurate and respectful as possible

It also received a number of spinoffs:

• The Amazon Trail (1993) — Takes place near the Amazon River in 1993 and involves some Time Travel
• The Yukon Trail (1994) — Takes place in 1897 during the Klondike Gold Rush
• MayaQuest: The Mystery Trail (1995) — Loosely based on the real-life expedition of the same name, follows the bicyclist player traveling in Mexico to search for code pieces required to stop a meteor catastrophe
• Africa Trail (1995) — Follows a team of bicylists journeying through Africa in present day
• Thule Trail (2007) — An advergame for Thule which follows a band of 20-somethings in present day who are going on a road trip to the Atlantis Music Festival in Santa Barbara, Canada and has a Denser and Wackier tone
• The Crystal Pepsi Trail (2016) — An advergame made with the partnership of Pepsi and The Oregon Trail brand and to promote the limited re-release of Crystal Pepsi; the game is set during The '90s
• Travel Oregon: The Game (2017) — A licensed advergame by Travel Oregon, which follows a road trip throughout Oregon in present day

The Oregon Trail remains a gaming classic and cultural icon which helped raise American dysentery awareness significantly, with parody musical The Trail to Oregon! and Zombie Apocalypse parody Organ Trail. It also happens to be the oldest title listed in the 2010 reference guide, 1001 Video Games You Must Play Before You Die, right before Pong.

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This game provides examples of:

• Adam Smith Hates Your Guts: Prices go up the farther along the trail you go. One of the people you talk to in the first game discusses this. Justified, given that supplies in the harsher wilderness would be harder to come by and cost more. If you can haggle well it is possible to buy supplies, leave town, and resell them for more than you paid, but the profit margins are thin, maybe about 10-20% per transaction.
  • Inverted in the second game for a few items — horses, for instance, were easier to find out in cowboy territory, and thus cost less the farther you go.
• Adaptation Expansion:
  • The Mac version of the first game was significantly changed from the original, including many more options for professions and changing the hunting minigame to first-person. Later versions even added a reloading requirement to the hunting sections.
  • Oregon Trail II adds more landmarks, a lot more options for supplies (including useless "supplies" that you're supposed to avoid, like the infamous grandfather clocks), and actual options for medical situations. Also, in addition to the titular Oregon Trail, you can travel the California Trail, the Mormon Trail, and the Applegate Trail. Rather than being limited to 1848, you can travel in any year from 1840 to 1860. There are different routes, settlements, trading posts, etc. depending on which year you choose.
  • Partially inverted with Oregon Trail 3rd Edition, which dropped the travel options added in Oregon Trail II, reducing you again to just the Oregon Trail in 1848. Also, rather than making up your own wagon party from scratch, you have to choose your party members from some people in Independence (similar to selecting a guide in The Amazon Trail). However, the same game added a Fishing Minigame as well as a Mini-Game for gathering edible plants. (In the original and Oregon Trail II, finding edible plants was a Random Event.)
• Anti-Frustration Features:
  • Later releases would give you the option to request items while bartering, whereas the original would make random, take-it-or-leave-it offers until you lucked into someone who had what you needed. Granted, 9 times out of 10 you'd simply be told nobody had any [x] to spare, but at least it was an improvement. You can also trade for items that, in reality, nobody would ever give you, such as food when the whole wagon train is starving.
  • In the original game, you could only take a limit of 100 pounds of food back to the wagon after hunting. From II onward, the limit increased depending on how many party members you have: usually in the low 200-pound range.
  • In II, hunting accidents such as gunshot wounds or animal attacks appeared at random after hunting. If you weren't killed instantly, you wouldn't fully recover for months, if at all. In 3rd Edition, these were self-imposed and much less deadly. An accidental gunshot wound would happen if you shot before you reloaded your gun, and missing a snake or a bear would result in a snakebite or mauling, respectively.
• Anti-Grinding: Continuing to hunt in a certain area (as a means to bypass the 100 or 200 pound limit) will cause game to become scarce.
• Anyone Can Die: Whether they are crushed by a wagon, drowned in a river, catch some horrible disease (cholera being the main offender, despite dysentery's memetic status, sometimes causing instant death), gored by an animal, frostbite, or shot, anyone on the expedition has the potential to end up dead before reaching Oregon. Hope you brought that medical book and wrote down the treatments!
• Arbitrary Headcount Limit: Your party has a maximum of five people, or six in the second version.
• Bilingual Bonus: The second game can take you to California, which was part of Mexico until 1848, and you can talk to characters who only speak Spanish. There's an in-game skill that automatically translates their dialogue to English — but if you yourself speak Spanish, you don't need to learn it in game.
• Bribing Your Way to Victory: The iOS and Android versions. You can buy "Oregon Trail Cash" to get the best wagon parts, skip crossing rivers, receive mission rewards instantly, heal sick family members, and buy supplies you couldn't normally get with in-game coins.
• Cap: Every item has a limit on how many you can carry. In the original: 20 oxen, 50 sets of clothing, 99 boxes of bullets, 3 of each spare wagon part, and 2000 pounds of food. There also is one on hunting: You can only carry back 200 pounds of food per session with multiple people, and 100 pounds of food alone.
• Credits Gag: The credits for Oregon Trail 2 contain credits for roles such as:
  • "Gaffer,"
  • "Only Person at MECC who knows what a Gaffer does,"
  • "Rogue Alien Oxen Space Craft,"
  • "Oxen that glow in the dark,"
  • "Silly Credits Inserts."
• Deadpan Snarker: The father/main character in the iOS and Android versions.
  Mother: Why doesn't [Daughter] ever talk to me?
  Father: [Daughter] hates you, [Mother].
• Developer's Foresight:
  • The second version offered a massive upgrade in stocking supplies necessary for heading west, which would eat up time browsing through each shop and rifling through every item. After you click anywhere in the embarking town, you are approached by a vendor for a package deal whose offerings depend on your occupation.
  • Also in the second and fifth versions, you can travel to California, which involves crossing the Sierra Nevadas at one of a number of points. If you travel in 1846 — when the Donner Party did — and find yourself at the same mountain crossing they took that autumn, you indeed get the exact same snowstorm that left them stranded for months, and it won't go much better for you. The game includes other historical freak weather/epidemics as well.
• Diabolus ex Machina: The game has a massive hard-on for sending down catastrophic misfortunes out of the blue:
  • Hey, wouldn't it be funny if, in the space of two minutes, a thief stole all but one of your oxen, and a fire wiped out almost your entire supply of food, clothing, ammunition, and spare wagon parts, just before your wagon's only remaining axle broke? No? Well, the Random Number God sure as hell thought so. Have fun starting all over, Mordecai!
  • The RNG is sometimes in such a hurry to kill your party that it forgets what logically should have done them in. It's entirely possible for Hezekiah to die from typhoid three days after getting a snakebite, or for Jebediah to merely break his elbow and then quickly succumb to the dysentery while you were trying to rest and recover.
• Dialogue Tree: From the Mac version onwards, you can talk to various people at forts and landmarks, and their dialogue is in tree form. However, it doesn't have any effect on the game besides boosting morale.
• Dramatically Missing the Point: The game designer actually made it possible to hunt animals like the buffalo into extinction, as an educational lesson. Didn't stop anybody from doing it, or even make them realize what they had done. Perhaps recognizing the problem with this, when you finish hunting in the PC/Mac port of the first game you're told "if you continue hunting in this area, game will become scarce."
• Dwindling Party: The game can and will be like this.
• Earn Your Bad Ending: As luck based and unforgiving as the games difficulty can get, it can be surprisingly tricky to get the entire party to die before you even reach the first Fort (a common fan-challenge) and requires a rather specific set of circumstances to occur.
• Edutainment Game: Ostensibly, it's about the journey settlers undertook in 1848. Most students who played it only learned how Nintendo Hard it was to get to Oregon in the first place.
• Emergency Food Supply Animal: If you go for a while without food, you will get the option to slaughter an ox for meat. From Oregon Trail II on, if a draft animal dies, it can be butchered for meat.
• Everything Trying to Kill You: All kinds of diseases and accidents are just trying to kill you and your party.
• Fake Difficulty: The hunting minigame is pretty simple, but mostly skill-based. Unless, of course, the game decides to stock the hunting area with loads of trees and shrubs around the margins of the screen, where animals will appear for a split second, turn back from the obstacle, and then disappear offscreen just as quickly. It's tough to bag any large animals in versions with 1st-person hunting controls when this happens, but it's outright impossible in older versions that use an overhead view, where these obstructions stop your bullets.
• First-Person Shooter: The hunting minigame, in later versions, anyway. The older editions' hunting game was more like Asteroids with bears, deer, and buffalo. The first ever version (released for a mainframe) required you to type "bang", "wham", or "pow" quickly, with misspelled words resulting in a failed hunt.
• Fishing Minigame: From Oregon Trail 3rd Edition on, you can fish in addition to hunt.
• Forty-Niner: You can become one in Oregon Trail II if you go to California at the right time. Upon arrival, you're given the option of either panning for gold or staking a land claim.
• Game Hunting Mechanic: The player can shoot animals with his rifle to get additional food. Buffaloes can even be hunted to extinction.
• Gameplay Ally Immortality: Averted. In addition to the ubiquitous dysentery, a later game made it possible (and very easy) to accidentally shoot one of your allies (or yourself) while hunting.
• Grave Humor: You can leave whatever text you want to on the graves. People who play after you will have the option to read your tombstones when they pass by where you died in-game. So you can guess what kind of crude and obscene messages kids left for each other.
• Guide Dang It!:
  • Fishing in the second game. It wasn't until the third edition that it became its own minigame, so in the second game, you had to have a fishing rod (or fishing net) and rest at a riverbank. This doesn't even guarantee that you'll catch fish.
  • In the same game, the way to survive the stretches of the trail with no water is to purchase water kegs at the beginning of your journey. Once you're out on the trail with no water, it's already too late to do anything about it.
• Historical Hero Upgrade: The actual John Sutter was a nasty piece of work: he enslaved, raped, and/or killed hundreds of Native Americans, including children. Several contemporaneous observers, including the governor of the region, considered the conditions at Sutter's Fort brutal even for the 1840s. NPCs present him in a largely positive light.
• I Just Shot Marvin in the Face: Later iterations add in the possibility of being injured or killed by accidental gunshots. Naturally, player skill has no effect on whether or not it can happen, although certain occupations and items lower the risk.
• Idiosyncratic Difficulty Levels:
  • The banker, carpenter, and farmer represent the three difficulty levels by starting funds (though the lower end may be offset by special abilities such as better oxen health, skill at wagon repairs, etc. in some ports). The Deluxe version added a number of new occupations, including the new hardest difficulty of Teacher, which had the same starting money as a farmer without the bonuses to oxen health.
  • 2 had its own take, as the player wagon was part of a train:
    • Greenhorn, the easiest, put the player in charge of a single wagon, with the fewest options to keep track of. Good performance (aka high morale) would offer a bump up to Adventurer.
    • Adventurer put the player in charge of not just one wagon, but also the route the train took — pacing, forks, etc. Poor performance would kick the player down to Greenhorn.
    • Trail Guide, the hardest, played like Adventurer with one caveat; poor performance meant getting kicked off the train and left behind. You do get paid $500 shortly into the game as a trail guide, which can be very helpful if you pick a lower paying occupation.
  • Also in OTII, you can choose to travel in any year from 1840 to 1860. Generally, the later the year you pick, the easier the game is, what with more settlements, more trading posts, more river ferries, etc. Hence, the game awards you more points if you travel in an earlier year.
• Informed Equipment:
  • You can lose your whole clothing inventory and your people still appear fully clothed.
  • Similarly, you can lose all your cooking equipment and have no means of starting a fire, but still eat meat (with no horrendous consequences to suggest it's raw).
• Instant Gravestone: The game contains this, including player-defined inscriptions. People tend to try to invoke Grave Humor with Bottom of the Barrel Jokes, as future players can read the gravestones.
• Instant Illness: Anyone that catches a cold will instantly spread it through the entire wagon party. This is a Justified Trope because the party is in very cramped quarters and colds are highly contagious.
• Instant-Win Condition: Reach Oregon and you win. The state of your health and general supplies might not bode well for your future, but hey, at least you got there.
• Joke Item: From Oregon Trail II onwards, you can purchase grandfather clocks and other furniture in Independence. Most of it is good for nothing other than unnecessarily weighing down your wagon.
• Jump Scare: The Apple II version is silent until you're ready to leave Independence. That's when a loud Yankee Doodle MIDI starts playing. This can startle even the most experienced players.
• Kaizo Trap: In The Oregon Trail 2, it's possible to die after reaching your destination and winning the game. How? Even after winning, staking a land claim, and seeing what lies ahead, you can still go hunting and accidentally injure yourself, get infected, and die. Demonstrated here.
• The Law Firm of Pun, Pun, and Wordplay: In OTII, the classic law firm of Dewey, Cheatum, and Howe appears in Independence at the start of the game.
• Low Count Gag: Probably an accidental one on the writers' part. One of the people you can talk to gives you the advice that you can shorten your journey and save on supplies "by taking all the shortcuts." Yeah, all two of them.
• Luck-Based Mission:
  • As tempting as it may be to label the game Nintendo Hard, it's impossible to do so simply because player skill has less than one might think to do with whether or not your party succeeds. Highlights include the floating of a caulked wagon (one of exactly 3 ways that can result in a Total Party Kill in the original game). A player could be within a mile of the end point with only the main character alive, just to have him be killed by a wild animal. Or the wagon could spontaneously catch on fire seconds after departing, instantly destroying most of your supplies.
  • Combine this with The Computer Is a Cheating Bastard. Good luck getting to Oregon when a thief comes in the middle of the night and steals all of your oxen. Strangely, your player doesn't shoot him after the third or so attempt.
  • How much you lose in the event of a failed river crossing is determined only by whether the crossing succeeded or failed. Some later versions added a couple variables, such as type of accident and susceptibility of particular items to spoilage, but that makes it only very random as opposed to entirely random. It's possible to survive a ferry wreck (you read that right; the safest possible option can still result in failure) while crossing the Mississippi at the height of spring floods and only lose a couple bags of flour, or to drown your entire party in one shot in the 2 and a half feet deep Platte river.
• Magic Antidote: Some stuff like gradually warming frostbitten areas and sucking out snake venom (though the latter is not recommended in the modern era with a modern first aid kit) can actually work. Heck, peppermint helps if you administer it to someone with cholera — the menthol eases the symptoms and allows the immune system to fight off the infection.
• Marked to Die: In 2 and 5, a party member can get ill to the point where their status becomes "critical"; this means that the character is in an irrecoverable state and going to die, but cannot because there is an impending event in play. You can do whatever you please during this time, but as soon as wagon progression begins again, the party member will die soon after.
• The Millstone: In 5 and 2, Nicholas J. Tillman is apparently an in-game millstone who cheats at cards and hinders your train as you go up hills. If you speak to him, he also gives horrible advice like rafting the rapids in the Columbia because it will be fun. He also wears bad suits.
  • Idiot Houdini: The fact that Tillman is even around to give you terrible advice about the rapids is impressive, since everything he brags about doing would realistically have gotten him killed 10 times over.
  • In-game, he's also related to Dr. Brogan Cavanaugh, a snake-oil salesman.
• Mini-Game: The hunting minigame can be used to obtain food. Also, the last stretch of the trail can be handled by a minigame to avoid rocks while the wagon is going down a river.
• The Missionary: You can meet Marcus and Narcissa Whitman in Oregon Trail II. Well, at least if you show up at the Whitman Mission prior to November 29, 1847. If you arrive on or after that date, you'll just find ruins.
• The Mutiny: Implied in the second and fifth versions. If you play as a trail guide and let the morale of your party get too low, you will get kicked off the train and your game will end. Since the only options are to save your diary or end the game, it's likely the game's way of telling you that your party abandoned you.
• Non-Standard Game Over: In the second game, you could be kicked out of the wagon train if you were a trail guide and did poorly enough, accompanied by a still of people looking angrily at you.
• No Party Like a Donner Party:
  • Discussed in the 5th version where everything that happened to them except what they're most infamous for is mentioned, which is clearly intentional to avoid upsetting kids. When it gets to that part the narrator simply says "They did things to survive that I don't want to talk about." One of the kids says "I heard that they-" before they told him to quiet down.
  • The leader of the Donner Party shows up in a town in the iPod version, too. He gives your party food, insisting that they've got more than enough to spare.
  • One fan comic◊ parodies this. Humorously, mysteriously gaining a bit of food if a party member dies while everyone else is starving was originally meant to be a game mechanic.
• Permadeath: Once someone dies, they're gone for good.
• Player Data Sharing: Some versions (for example, the Windows 95 version) allow you to encounter the tombstones of player characters that didn't make it to Oregon.
• Politically Correct History: In the 5th version, they added cartoon segments throughout the game showing the journey of three children— Cassie (who's also the narrator), Parker and Jimmy— and their African-American trailblazer Captain Jed Freedman to reunite the kids with their father in Oregon.
• Press X to Die: Each game, especially the later editions, have options that are guaranteed to result in party members dying.
  • The original version of the game has the Green River. Attempting to ford across this river will result in everyone drowning. The Oregon Trail II also adds the Mississippi River and Missouri River, which are even deeper than the Green and just as guaranteed to kill anyone trying to ford them.
  • The second edition of the game adds the ability to select treatment options for injuries and illnesses, such as suggesting exercise for rattlesnake bites, or rubbing salt into gunshot wounds
  • In the 3rd version, gathering plants is an option and you may be presented with some poisonous ones. By picking them, you can intentionally get your party members or animals sick. Sometimes, they'll get tossed instead.
• Public Domain Soundtrack: The soundtrack, such as it is, consists of 8-bit renditions of songs from the public domain when you reach the landmarks, such as "Yankee Doodle" in Independence, Missouri; "Billy Boy" when you reach Fort Laramie; "Charlie is My Darling" when you reach the Soda Springs... and even "Believe Me, if All Those Endearing Young Charms" (usually used in a Xylophone Gag).
  • Oregon Trail II uses original compositions for the travel screens and so forth, but period songs are still used for visits to towns, forts, and trading posts. They're assigned randomly rather than being permanently associated with any specific place (except for Salt Lake City, which always has "Come, Come, Ye Saints").
• Purely Aesthetic Gender: In the earlier games, the names you choose to give your party members are the only indication of their genders. Presumably, the game doesn't recognize any difference between a party member named "Alice" and a party member named "Bob". And when you use gender-neutral names like "Fartface", who can even tell?
• Pyrrhic Victory: Arrive in Oregon with a sole surviving party member; you made it, but the rest of your family is dead as a result. You yourself may even be sick, penniless, and dying during the height of winter at this point.
• Railroading: In Oregon Trail II, if you try to travel the Mormon Trail in 1846 (the earliest year it's offered as a choice), the game forces you to stay in Winter Quarters (just across the Missouri River from Kanesville) until spring of 1847, just as the real Mormon pioneers did. It doesn't matter if it's February and the spring of 1846 hasn't come yet, you cannot leave Winter Quarters any later than spring of 1847 because history says so.
• Random Number God: The game arbitrarily decides how often to throw problems at you, and how severe the problems can be. Also when it comes to events like failing to cross a river or having things stolen, the game simply randomly selects what is ruined in the water/stolen and it can be anything from a bag of flour to all your animals.
• Role-Playing Game: Especially Oregon Trail 2/5, in which you could have special skills. Oregon Trail 5 further added a point-based character creation system.
• Save Scumming: Quite often you'll find yourself saving your game due to the whole game being a Luck-Based Mission and how Random Number God dictates the events; they can be quite frequent and will often come at the worst possible times, especially if the outcome is detrimental to your party.
• Scare Chord: II (and 5)'s infamous DUN DUN!
• Scoring Points: Most versions of the game have a score calculating algorithm based on surviving party members, party health, and supplies. Then the profession you started as is applied as a multiplier - for example, in the first game starting as a banker ($1600 starting money) didn't grant any modifier, starting as a carpenter ($800) granted an x2 multiplier, while starting as a farmer ($400) granted an x3 multiplier. Later versions added more jobs, some of which had abilities that made the game easier and reduced the multiplier - for example, farmer and teacher both started with $400 but a farmer's animals were less likely to get injured so he got an x3 multiplier, whereas a teacher had no abilities and got x3.5. Of course, the main reason anyone cared about the score was making their high score named ASS.
• Shop Fodder: In the second game you can buy things like china sets and grandfather clocks that just make wagon tipping more likely and give you something to trade with people.
• Shown Their Work: Characters can die unexpectedly from gun shot wounds while hunting, drowning, or all manner of random ways, while also be constantly hampered by disease, broken parts, and supply shortages. All this was very common to real life wagon trains.
• Shout-Out:
  • At the end of the intro sequence to the same game, you see a fur trapper, with two young girls in his lap, turn to you and say, "Well, are ya ready? Let's go!" From their clothing, positioning, and the background, it appears that this is intended as an homage to the Emanuel Leutze painting Westward the Course of Empire Takes Its Way.
  • In Oregon Trail II there's a Running Gag about character named Nicholas J. Tillman who always gives terrible advice about your journey. (Sample in-game journal entry: "Arrived at _____, despite some 'help' from Nicholas J. Tillman.") He's named for a very similar character in an older MECC game, Zoyon Patrol.
  • In the iPod version of the game, the silly things your children might say while traveling include "I am a banana!" and "I am the Queen of France!". They might also suggest you "Do a barrel roll!" during a bear attack.
• Soundtrack Dissonance: As the status of your party got worse and worse, the music would become more and more frantic/depressing, with Scare Chords in the soundtrack if they're in poor condition. But since this only accounts for the living, if a sick party member dies and there aren't any more sick people, THE MUSIC RESETS TO THE CHEERFUL THEME. Also a form of Mood Whiplash.
• Spin-Off: There's The Yukon Trail and The Amazon Trail mentioned above. And then, you know they want a piece of the Farmville pie when the developers put out a Spin-Off that requires you to build a town, that's played pretty much the same way as Farmville including buying premium buildings with real cash. Now you can have Farmville in Oregon!
• Super Drowning Skills:
  • If you ford a river that's too deep, your caulked wagon tips over, or (rarely) your ferry breaks loose from moorings, some of your party members may drown in the river. Likewise when you raft down the Columbia River, and crash into a rock or (in the Apple II version) the shore.
  • Sometimes your wagon can tip in a flooded trail or two feet of water.
  • And people can almost drown in a foot of water without the wagon tipping. Were they trying to do handstands in the middle of the bloody river?
• Super Not-Drowning Skills: In Oregon Trail II, the riverwork skill increases your chance of successfully crossing a river — even if that chance is normally 0%. This means you can potentially ford rivers 12 feet deep or more and come out completely unscathed.
• Toll Booth Antics:
  • Several river crossings give you the option to pay someone to use their ferry to cross; otherwise your choice was to either try to ford the river as is (at risk of being swept away by the current and losing supplies or people), caulk your wagon and float across (ditto), or wait a day to see if conditions improve (lose time and supplies on eating). Whether for Watsonian reasons of wishing to save money and/or feeling confident in one's ability to caulk their wagon and float across, or Doylist reasons of not wanting to be called a coward by one's own classmates, guess what most players chose to do.
  • At The Dalles near the end of the Trail is the Barlow Toll Road, which will lead you to Oregon City for a price. Your other option is to get on a raft you built and float all the way down on the rocky, swiftly running Columbia River. Again, guess which way was chosen approximately 95% of the time.
• Too Dumb to Live: You, potentially. So the Snake River is 16 feet deep and rated Extremely Treacherous? Let's ford it! Dysentery? Go jog it off, you'll be fine! Hell, why not just buy a bunch of grandfather clocks instead of livestock to pull your wagon, or trade your livestock for odds and ends while in the middle of nowhere?
• Total Party Kill: The most common ending.
• Travel Montage: From Oregon Trail II onwards, the travel screen uses the old "line moving across a map" effect.
• Unexpected Gameplay Change: The hunting minigame and the river-riding segment at the end.
• Vague Hit Points: The health may by "good", "fair", "poor", but the number is not directly shown. There's even less feedback concerning exact health of the players with you.
• Videogame Cruelty Punishment: If you neglect burying bodies in Oregon Trail II, morale takes an EXTREME drop. See You Lose at Zero Trust.
• Videogame Remake: Quite a lot of them; a special note is the fifth edition being largely a remake of the second game, which is literally the exact same game with a couple new mini-games, and they added cartoon segments throughout the game.
  • The 3rd Edition is a throwback directly to the 1st game, with fewer options than the second game when you have to make decisions.
  • Thule Trail, sponsored by bike rack manufacturer Thule, is Oregon Trail on a modern road trip from Chicago to a massive concert in LA. You can choose between a SUV (comfortable but expensive), a hybrid car (cramped but cheap), or a turbo wagon (fast but expensive as well).
  • And a fan-made zombie version, Organ Trail.
  • There's also Crystal Pepsi's version of the game called The Crystal Pepsi Trail, with some 90s nostalgia.
• We Cannot Go On Without You: From Oregon Trail II on; the main character's death (or in the second and fifth editions, dismissal as a leader if you choose the trail guide option) ends the game, even if the other party members are still living.
• The Wild West: The game takes place in 1848 (later installments expand from the late 1830s through the early 1860s) and has you traveling the Wild West.
• Wizard Needs Food Badly: Usually not a problem, given that buffalo are plentiful, huge and slow targets, and provide more food than can be carried back to the wagon. Can be a problem if you're, say, trying to cross a desert without buying a crapload of water containers first. Or if you forget to vary your party's diet and they all come down with scurvy or beriberi. It's easy to have your whole party die in the desert because even though you bought the canteens, they are usually the first things to go if you tip in the river. Can also be a problem if you lose all your bullets or gunpowder (if you've been using a shotgun) in a river crossing/Hill tip, or food and then cross the deserts since there's only the very hard to hit pronghorns and ground squirrels/rabbits and their population numbers are smaller. Can also be a problem if you forget to buy enough food in the early stages of the trail and find yourself running low in arid Western territory with few settlements and scarce wildlife. This is, of course, Truth in Television.
• Worst Aid:
  • In the second game, rubbing snow on frostbitten areas (this "treatment" was actually used until the 1950s) is an option. OUCH!
  • The game provides you with many options to treat injury or illness, one of them usually being the very worst thing you could do. Go ahead. Rub some salt into that gunshot wound. It'll keep them from being infected.
  • How about "exercising" a broken limb?
  • Got snakebite? Just run some laps, you'll be fine.
  • Got Cholera or Dysentery? ADMINISTER EPSOM SALTS!!! ^note Due to a bug, epsom salts are actually the best possible treatment for cholera in Oregon Trail II.
  • In Taxman's LP of Oregon Trail II, the Goons told him to (predictably) bring tons and tons of laudanum. Sick with absolutely anything whatsoever? Have some laudanum! Got to love 19th century medicine. Laudanum is whiskey diluted with grains of opium, and prior to opium becoming a controlled substance, people actually would take laudanum for their headaches and such. As you might guess, taking what amounts to a whisky/heroin cocktail might fix your headache, but causes some very real other problems.
• You ALL Look Familiar: In Oregon Trail II, there are a dozen or so people you keep seeing over and over again. In some cases, it's clear that the same people are meant to represent different characters.
• You Lose at Zero Trust: When playing as an adventurer or trail guide in OTII, your job depends on the morale of the wagon train, which is a reflection of their confidence in you; once it drops below a certain level (even if due to factors outside your control), a bunch of angry people will appear and forcibly demote you. If you're an adventurer, this just means you continue as an ordinary pioneer, but if you're a trail guide, the game is over. Morale is based on the health of the party, and factors such as success at river crossings and food amounts. If you also refuse to bury your dead, it will plummet.

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This Troper has died of dysentery.