In the computer lab of every 90s elementary school, there was one piece of software that transcended time, transcended geography, and probably taught us more about life than any other piece of clunky early ‘edutainment’ software: The Oregon Trail.
You’d click through that gray-blue screen, choose your character’s occupation (banker, carpenter, or farmer—everyone knew being a banker was cheating), and suddenly, you were no longer a kid in some fluorescent-lit classroom.
No, you were a pioneer. You were on a journey that could end with a triumphant arrival in the Oregon Territory or a lonely, pixelated death somewhere near the Snake River. And even if you “won,” you knew there was a real possibility your entire family would be left in unmarked graves along the trail.
And somehow, this was deeply entertaining. Looking back, there was something hilarious about how casually morbid it all was. You’re 9 years old, sitting between kids in slap bracelets and neon windbreakers, and suddenly, your screen flashes: “Emily has died of dysentery.” Dysentery! It wasn’t even a word you fully understood, but it sounded dreadful, like a medieval affliction nobody should be dealing with in 1848. Then, a few more clicks, and someone else in your wagon party gets cholera or typhoid, and it’s all downhill from there. You could attempt to trade with other pioneers, barter for medicine, or try to ford a river that always looked too deep. But you knew—deep down, you knew—someone was probably not making it to Oregon.
The Oregon Trail wasn’t just a game; it was a bizarre lesson in risk management and the utter randomness of life. You’d sit there calculating how much food to buy or debating whether you could risk another box of bullets in case a buffalo came along, only to be reminded that none of it mattered when fate was as random as a coin flip. It was nihilism wrapped in pixel art. You could do everything right—buy enough food, hunt until you were out of ammo, pace your oxen—and then, out of nowhere, the game would gleefully inform you that a wagon axle had broken or your child had contracted a fatal illness. The Oregon Trail was like a preteen introduction to existentialism, and we didn’t even realize it.
And hunting! Let’s talk about the hunting. At some point, you’d hit the “Hunt” button, a game-within-a-game, and suddenly you’re facing an endless stream of bison, bears, and squirrels that seemed to cross your path in a forest with just one tree. You’d shoot wildly, stocking up on more pounds of meat than you could ever carry, which was, of course, the other lesson of The Oregon Trail: the futility of over-preparing. You’d shoot enough bison to feed a small town, but the game would mockingly tell you that you could only carry a fraction of it back. It was almost an ecological parable, except it probably just made us better at button-mashing.
And there was a deep social currency in the game. Nobody talked about math class on the playground, but everyone knew about The Oregon Trail. You’d compare notes with friends, bragging if you actually made it to the Willamette Valley or recounting tragic tales of your party’s demise. Did you attempt to ford the river? Everyone knew the caulk trick worked better, but sometimes you just had to risk it. Did you choose to rest when morale got low, or did you soldier on? Did you waste your ammo on squirrels, or were you disciplined enough to save it for the buffalo? The Oregon Trail was an entire subculture that predated the internet—shared experiences of fictional survival that bonded us all in the silent understanding that, someday, we might just have to go out there and ford a river ourselves.
And somehow, after all that trauma and chaos, it was supposed to be educational. You’d finish the game and feel like you’d learned something meaningful about history, which was mostly that pioneer life was short, brutal, and relentlessly unfair. But there was something powerful in the realization that every journey could end differently. Some days you made it through the river crossings with ease, and other times, your wagon capsized, your supplies were gone, and the game left you with that bleak but unshakable truth: sometimes, no matter what you do, life just doesn’t go your way. And the best thing you can do is start over and try again.
Related Posts:
