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I THOUGHT THIS WAS WORTH SHARING

Scott Muska is a writer who keeps his belongings in Chicago and most of his other things in books and on the internet. This is a collection of some of those things. (If you’re into it, he has two books available on Amazon, or by mail if you hit him up.)

Occasional Dispatches From a Night Spent Playing ‘Oregon Trail,’ for Some Reason

6 min readApr 16, 2025

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As I chain-eat Airheads and play this classic game on my laptop while binge-watching episodes of Summer House, taking intermittent breaks to rip blinkers and view several TikToks, I have to wonder if I am spending my time and channeling my energy in the best possible ways. Novels do not write themselves and bodies are not sculpted while playing a video game from the ’80s in a sedentary position. At the very least, I could be learning to type more accurately and efficiently by playing a Mavis Beacon game. But, buy the axels, take the wagon ride.

I’ll never forget one of the first times I played Oregon Trail. Mostly because at one point my smokin’ hot computer lab teacher came up behind me and her breast lightly grazed my shoulder. I couldn’t get up from the computer for like half an hour. For obvious reasons. In that span of time I managed to die of dysentery several times.

There is potential that I have staffed the crew for this adventure in what you might call not the most prudent or best way. In an attempt to delve into the furthest depths of nostalgia I can achieve, I admit I acted rather impulsively. I am playing this game like I would have back in middle school, which means bringing at least two women I am attracted to with whom I could imagine a future if things were to work out in a certain way. With one of my best friends along for the ride. Leaving room for a single rando in the wagon named Cady (unclear why she spells it this way; she contains multitudes), who I met and vibed with while preparing for my voyage in Independence, Missouri. We’ll see what happens with her, if anything. So this ragtag, incongruous group is comprised of Cady, Karen, Shannon, Brody and myself.

Brody is not my best friend, but he is probably the most outdoorsy and resourceful person I hang with, so I think I made at least one smart choice vis-a-vis a comrade who can pitch in when it comes to fixing wagon wheels or figuring out how to ford a river. At lunch (we worked together in finance), the dude would just hang out in the corner of a room whittling stuff, was often wearing something accented with fur and the only things I ever saw him consume were beef jerky and rotgut whiskey. Seemed pretty rugged and I assumed he enjoyed hunting.

A banker from Boston, it remains unclear to me why I must begin my journey from this specific town of Independence, but I don’t make the rules. I hope the group minus Cady didn’t already get annoyed with each other while making our way down and over here. Why’d I leave Boston in the first place, anyway? And why am I heading for the great unknown? My character must have gone through one hell of a breakup or something and really has to shake things up. The dowry he offered his wife’s family may not have been enough, and he got shot down by her pops when he asked for her hand. This is the narrative I choose to construct. I’m a sucker for a sojourn in which the protagonist tries to find solace in the road to keep his mind off shattering heartbreak.

I have to wonder if Matt from Matt’s General Store is trying to hustle me. If I were him, I surely would. it’s probably readily apparent that I don’t know shit about what I am about to do, and am woefully ill-prepared. And Brody’s not exactly helpful. Dude just keeps throwing more and more salted meats on the counter, along with a startling amount of ammunition. (I’m starting to realize he’s of the ilk that would storm the Capitol Building if a bunch of people told him it was a good idea, and that’s harrowing.) I figured going overboard on both these things wasn’t necessary. I love a salty snack as much as the next guy, but if we’ve got all these bullets we should be able to shoot some fresh stuff, right? But I don’t wanna rock the wagon at these beginning stages, so I acquiesce. Even let him throw some black licorice onto the order, even though it is absolutely disgusting and his adoration of it further bolsters my burgeoning theory that he is at least a low-level sociopath.

One of the things the game asks me early on is when I “want to leave Independence,” which takes me to an existential place. If anything, boldly forging out into the frontier is, like, one of the most independent things you can do. I’ll later find it would’ve been more accurate for the game to ask me during which month I’d like to go ahead and abandon all hope.

It’s no wonder bison is a delicacy now. Probably because people on the Oregon Trail were just shootin’ the shit out of them for a real long time, with reckless and unnecessary abandon, if the mechanisms of this game are to be believed. What some do in life fucks over future generations. I blindly assumed Brody was gonna crush it on the hunting front, but his performance hasn’t been exactly accurate. It’s no wonder he wanted all that ammo, as he goes with the “spray and pray” method, which ain’t exactly tried and true. But when you’re firing like that, you’re eventually going to hit something, and he takes out three fully grown beasts during our first little side expedition that we embark upon because the ladies are swiftly growing tired of jerky, and none of us have had a satisfying bowel movement in a startlingly long time due to our diet. (Turns out, girls do poop. Allegedly. Or they talk a lot about not being able to comfortably or regularly do so when that occurs.) But, like, we can barely fit one carcass in our wagon, and have no choice but to just leave the other ones there, dead on the ground. I tell him to absolutely not do this again, or we’re gonna run out of bullets. He shrugs and fires one into the sky.

Brody had some solid ideas for fording our first river. Or at least I thought as much. Turns out he didn’t really know what he was doing. And also neglected to tell any of us he could not swim. I’m sure gonna miss that guy. Guess he won’t be trying to cap bison and other wildlife with impunity anymore. But we forge on, now with the estrogen and testosterone balance tipped very much in the favor of the former.

Cady and I consummated our love late last night, while the others slept around the fire. It was tender and lovely. But after it ended, I was met with the cold shoulder. Am I being used? Is this simply a situationship? An attempt to muster a salve to the loneliness that comes with the open dirt road, no matter who you’re with? I can’t help but wonder if we would have hit it off if we met in a Boston pub, or if this is just a temporary coupling out of convenience and lack of other options (for both she and me, as she’s made it plain she is straight as an arrow and neither Karen nor Sharon have sent any signal whatsoever that they have designs on me)?

Guess I’ll never find out. Cady succumbed to Syphilis a couple days ago, near the break of dawn while the rest of us slumbered. I did not know she had such an affliction and now I am of course very frightened for my own health. Honestly didn’t know that was a malady you could perish from in this game. Must be an updated version or something.

I actually just Googled Syphilis because I didn’t know too much about it other than it did Van Gogh pretty dirty. Seems very very nasty to say the least. This got me curious about other STDs and before you know it I was down a rabbit hole and for once being thankful that I am currently very far from sexually active. I might be the only person who wants someone to check their Google search history if they die (maybe of something like dysentery), because it would be really hilarious.

Well, looks like dysentery is going to get me after all, without even making it farther than the Midwest. So it goes. Hope Karen and Shannon are able to glom onto another group and forge ahead.

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I THOUGHT THIS WAS WORTH SHARING
I THOUGHT THIS WAS WORTH SHARING

Published in I THOUGHT THIS WAS WORTH SHARING

Scott Muska is a writer who keeps his belongings in Chicago and most of his other things in books and on the internet. This is a collection of some of those things. (If you’re into it, he has two books available on Amazon, or by mail if you hit him up.)

Scott Muska
Scott Muska

Written by Scott Muska

I write books (for fun), ads (for a living) and other stuff (that I often put on the internet). I live in Chicago if you ever want to hang out. I need friends.