The One Lesson from The Oregon Trail We All Missed

Today’s guest author is Oliver Lyons. Please check out his other contributions in the archives.

It’s 1993 and there is goddamned LINE outside of my 7th grade homeroom classroom. Kids willingly woke up early and got their parents to drive them / hitchhiked, I guess? to school so that they can be one of the first in line when the teacher opened the classroom door at 7:30am. Why? This classroom had a computer with a video game on it. 

The Oregon Trail was developed by Don Rawitsch, Bill Heinemann, and Paul Dillenberger in 1971 and produced by the Minnesota Educational Computing Consortium (MECC) in 1974 (thanks, Wikipedia!). It was an educational computer game designed to teach school-children about the hardships of life 19th century “pioneers” (*cough* white settlers *cough*) endured as they traveled from Missouri to Oregon’s Willamette Valley via covered wagon. The game went through many iterations from pen and paper, to DOS, to apparently a 2023 version you can purchase for Xbox (I cannot even imagine the depths of hell the lobby for that game must be like!?!) But the versions most of us (i.e., people in their 40’s with chronic lower back pain) remember are probably the 1990 DOS version, the 1991 black and white version for Mac, or the 1993 DELUXE version for PC. 

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The game itself is mostly a simulation. You decide what type of character you want to be (banker, teacher, saddle maker, etc.) and how many people you are traveling with, and then choose what supplies you’ll start out with based upon your character’s budget. From there you mainly watch your poorly rendered covered wagon run in place across the top of your screen while text below in the form of diary entries explain what’s happening. You can control when and for how long your group rests, when to buy supplies at forts along the trail, and the pace you’re traveling at but, beyond that, the only actual “video game” elements you control are the hunting mini game (where you shoot at poorly rendered animals that run across the screen at various speeds) and the rafting mini-game at the end (where you dodge poorly-rendered, erratically moving rocks). Still, in the early 1990s we couldn’t have cared less. We got to play (technically) a video game in school! Most of us didn’t have home computers, let alone computers capable of rendering even rudimentary graphics. So this ‘edutainment’ simulator was basically Elden Ring to us twelve year-olds!  Definitely worth waking up at the ass crack of dawn to hopefully be one of the first few kids in line to get to play for twenty minutes before the 7:50am bell rang!

I know I keep harping in the crudeness of this game, but it actually had a few elements that were ahead of its time, including inventory management, killing, and death. Mainly death. This is the game that taught us 7 out of every 10 people in the mid 1800s died of dysentery. Or snakebites. Or the measles. Or because they couldn’t RAFT DOWN THE RIVER CORRECTLY! Holy shit, Brian! I told you to let me play when we got to the river part!! I’m going to beat the crap out of you at lunch and steal your Yodels!! 

*Ahem*…Yep, no matter how hard you tried, SOMEONE in your party was not going to make it. And once they died, the game made you stare at a poorly rendered image of people grieving at an unmarked grave. It was a bit heavy for 7:30am on a Tuesday. Sometimes, actually most times, EVERYONE in your party would die as a result of disease, lack of clean water, starvation, wagon fires, or you being a dumb shit child not understanding the game’s mechanics. The game could take anywhere from a half-hour to several days to complete depending on a variety of circumstances, and because myself and most of the kids I knew played it in short bursts before class or during lunch, it was rare to see someone actually beat The Oregon Trail. Much to the designers’ regret, we kids were more concerned with getting the highest score we could before our teacher kicked us off than actually learning anything about the dipshit travelers who failed to do what the Native Americans had been doing relatively easily centuries before they got there.

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Eventually, most of us got home computers and some of us even found cheap old copies of The Oregon Trail. And because people now had much more time to spend with the game, certain strategies started to reveal themselves. So, for those of you still interested, here is the definitive guide to beating The Oregon Trail:

  1. Start as a farmer
  2. Buy 5 oxen, 10 sets of bullets, 5 sets of clothes, and 1 of each wagon part before you head out on the trail
  3. Leave in April
  4. Set your pace to ‘Strenuous’ but make sure to rest every time your party’s health drops to ‘Fair’
  5. Ignore everything I said before, start as a banker or doctor and play however you want

Oliver, are you making this about capitalism again like you did with the Hess truck? I absolutely am. But this time I’m grasping at far fewer straws. 
Starting The Oregon Trail as a banker gives you $1600 to work with (doctors get $1200). Compare this with a teacher or a farmer who both start with $400 (#brokeboys). As a banker, you can max out all the supplies you’re allowed to buy at the beginning of the game (20 oxen, 50 sets of clothing, 100 boxes of bullets, etc.) including 2000lbs of food and STILL have ten bucks left over to pay for some ferry tolls! Yeah, $5 gets you ferried safely across most of the rivers in the game. Otherwise, you can take a chance with floating your wagon across or fording the river but, good luck there! Heck, you can HALVE those supplies and still be way better off than you would if you started the game as a teacher. 

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When you play as a banker or doctor, you can literally throw strategy out of the window. Start in August as what’s a few snow storms along your journey when you have plenty of food and more clothes than Cher in Clueless?! Travel at a ‘grueling’ pace as you have 20 oxen to run into the ground and leave dead by the side of the road (and you can always buy more!) Get all the dysentery you want because, if you’re a doctor, you have access to the most popular snake oil of the day which can fix you right up! Heck, you don’t even have to risk rafting down the river at the end of the game! Just take the toll road instead and moonwalk into the Willamette Valley four months later with all of your supplies, everyone in good health, and some cash in your pocket which you can use to swindle more Native Americans out of acres of land that’s rightfully theirs (presumably)! 

Even hunting becomes optional as opposed to a necessity when you play as a banker or doctor because, in later versions of the game, the food you hunt spoils but the food you buy does not, so stock up at the forts and then kill some time blasting those crudely animated buffalo and moose straight to animal hell with no worries about how many bullets you’re wasting or how much food you can’t carry back with you! Even if your supplies get stolen, fall in the river, or burn up in a random, game generated wagon fire – you’re rich! You can always just buy them again at the next fort! 

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Unrelated picture of some asshole for no real reason

When you play as a farmer or teacher, the entire game changes. You really have to manage your inventory and make sure to get plenty of rest along the trail because that 5lbs of rabbit meat that took ten bullets to get sure as shit isn’t going to stop the measles! You’re also going to get sick more often because you have less clothes, move much slower because you have less oxen, and you can forget about taking a pleasure cruise across the rivers. You’re going to be floating or fording those bastards! And, yes, you will be rafting down the murder river at the very end of the game! 

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Now, you’re probably thinking to yourself, “for a game made by educators, they sure do seem to hate teachers?” To which I say, THEY don’t hate teachers – society does. I’m writing this in August of 2023 when the GOP ghouls all vying to be the next dictator of America just had their first debate where they made it crystal clear that teachers’ unions were public enemy #1. 

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      Another unrelated picture of an asshole for no real reason

This is a tale as old as time. It’s the real lesson The Oregon Trail wanted to impart. Sure, according to the guide, playing as a farmer means your oxen are less likely to get sick, but when you’re a banker, oxen are as replaceable as your childhood pets! And, yes, playing as a banker gives you less overall points which means you don’t get to be a “trail guide” on the list of legends at the end. But do you know what you do get to be? Alive. And healthy. And, I can’t stress this enough, still a rich banker. The rich who provide no value to society will win. The poor who keep society running will suffer and most likely die. No, money can’t buy happiness, but it absolutely can keep dysentery away! The game developers knew this. In fact, banker is the character type already selected for you when you boot up the game. They were purposely trying to make their game as easy as possible for their audience of eight year-olds. You have to actively CHOOSE to play as a character with fewer resources. You can struggle as a noble farmer and die a “trail guide”, or play as a rich banker and win the game. I know it would be hard to get a game published in 1971 called “The Pale-Faced Land Thieves Need to Die Before They Can Further Implement Their Imperialist, Capitalist System Across the Nation” but I’m glad the developers still included that philosophy in The Oregon Trail we got. It’s a shame most of us were too busy figuring out what “fording the river” meant to learn it.

Play the 1993 Deluxe version of The Oregon Trail for free here

Play the 1990 DOS version for free here

Find and support your local teachers’ union here

Donate to the Native American Rights Fund here

Oliver is no longer on whatever Twitter is now called. He asks that you support the causes above or just be kind to any buffalo you happen to encounter in the wild. 

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