GRWM to Die of Dysentery: A Modern Woman Takes On “The Oregon Trail”


There are many reasons why people left their homes to travel the Oregon Trail: a better life, free land, exploration. Mine was to get off TikTok. Instead of writing or at least reading, I, like many other geniuses of my time, find myself scrolling my never-ending TikTok feed. Recently, the lack of control over my For You Page has swung my emotions like a pendulum: For every Tarot card video I saw that really had me thinking he’d text me back, I got a “what to pack for an apocalypse” clip. For every GRWM video, one about a grisly unsolved crime was certain to follow. To make a long story short, my days of doom scrolling were over.

Around the same time I committed myself to avoiding my chaotic FYP, I got a new iPhone with three free months of Apple Arcade. I figured I’d download Solitaire or some other simple game, but I was shocked to find a game buried deep in my childhood memories: The Oregon Trail. The logo was the same, but everything else looked new and colorful. I immediately downloaded the game to my phone and was off to the races — the kind with wagons, three oxen, and endless ways to die.

For those of you who never had the pleasure, The Oregon Trail was first released in the 1970s as an educational game for kids to learn about life as a 19th-century pioneer. The goal of the game was to successfully lead your wagon party from Independence, Missouri to Willamette Valley in Oregon. The game sounds simple, but anything could throw you off the trail: thieves stealing your supplies, an ox running away, forging a wild river and failing, someone breaking a leg or arm, running out of food. Finding the end of the trail, if you ever find it, feels like winning the lottery.

“Finding the end of the trail, if you ever find it, feels like winning the lottery.”

When I first played in elementary school computer class, I don’t think I ever got halfway through the game. My core memory involves the message, “You’ve died of dysentery,” flashing neon green on my screen before it went blank. Hindsight is 20-20, and I personally think the game could’ve been more successful in terms of historical education. My big takeaways were learning that you can die from shitting yourself (dysentery) and that I couldn’t type “POW” or “BANG” quick enough to shoot any game. However, in the year of our lord 2023, I committed myself to making it not only to the first fort, but all the way to Oregon.

Luckily for me, the new iteration of the game hasn’t become too dynamic to the point where I can’t play.. The Oregon Trail still remains a game about successfully traveling to Oregon, but there are a few new bells and whistles that really drew me in. The creators include different quests within the game specific to historical figures, such as James and Margaret Reed of the infamous Donner Reed Party. When I met them on the trail, I gave them fifty pounds of meat and prayed I could rewrite history with my generosity.

The game's creators also worked with Native American scholars to properly depict indigenous perspectives on westward expansion and include characters and side quests that reflect their uncertainty of welcoming pioneers into their homelands. Seeing as it’s been years since I took AP US History, I appreciated the refresher on Manifest Destiny. But my favorite new feature: the wily wagon party characters.

“When I met them on the trail, I gave them fifty pounds of meat and prayed I could rewrite history with my generosity.”

Unlike the old game, where you just got stuck with a random family that couldn’t do anything, this new version gives you opportunities to choose specific players for your party: a banker, a farmer, a missionary, an adventurer. All of these characters have different traits that could make or break your game, traits like Heroic, Brilliant, Strong, Frail, Hedonism, Pugnacious. My first go-around, I didn’t take these character traits too seriously, that is until one of my farmers (Hedonist) ate half our food supply and my missionary (Slack) left the party no less than four times because the conditions were too tough. Also, try getting a frail farmer to change a wagon wheel—not only will the wheel remain broken, but he’ll probably break his foot in the process.

It’s like playing The Sims if they all lived in a covered wagon, and let me tell you, I didn’t factor babysitting four digital adults into my game play. However, my first banker, basically the ancestor of the Silicon Valley Patagonia-wearing tech bros, learned how to fish and hunt! He became adventurous and let the pixelated land teach him how to live off of it. Nature heals.

The first time I made it to Oregon was the same day I downloaded the game. I played 5 hours, determined to get to the end of the trail. Whenever spiritual self-help articles speak of pleasing your inner child, I’m pretty sure they’re referring to the sheer joy I experienced seeing my eccentric wagon party jumping up and down as they entered Oregon.

After I finished the game, I wasn’t left with an empty feeling I typically get after mindless hours of TikTok. I was left wanting more of the trail, more of the silly characters, more of the antics, more of the ridiculous auto-generated gravestones that appear when someone dies. So I continued playing different quests: traveling as a cook for a group of picky eating cowboys, embarking on a winter migration with minimal food and grumpy characters, and even taking a scenic nature trail where the goal was to collect different species of animals. All the free time I had left over from TikTok went straight to learning how to properly forge a river and not get cholera. But today, I’m left wondering: how far is going too far on The Oregon Trail? Could my game play pose a problem for my writing and my other priorities?

“But today, I’m left wondering: how far is going too far on The Oregon Trail?”

At the top of my morning writing group’s meetings, our leader pulls one of Brian Eno’s Oblique Strategies to inspire our writing session. A card she pulls often reads, “Repetition is a form of change.” When I first started seeing this card, I called bullshit on its message, considering all the times that repetition has led me to lean on substances (including TikTok) to avoid facing my feelings or dealing with discomfort. The nights out where one martini easily became five. The mornings where a puff of a joint slowly consumed a whole day. The things I did for fun to fill my void of free time became binding and left me hollow, always craving more.

Repetition changed me into someone I didn’t enjoy, and I find it only natural to fear falling into this trap with new interests or ways to pass my time. I’ve only recently realized that “repetition” and “change” don’t have an inherently positive or even a negative connotation—it is all what you choose to change or repeat. Repetition can be a form of change however you can also change what you repeat if you desire a different outcome. You can start over at any point.

Right before you begin your game on The Oregon Trail, a message flashes on your iPhone screen: “If for some reason you don’t survive—your wagon burns, or the river steals your oxen, or you run out of provisions, or you die of cholera—don’t give up! Try again… and again… and again…” There’s an odd hope to the game when you take a step back and understand what it means to risk everything for a new way of life, a hope that extends into choosing how to spend the time I have. An infectious hope from crossing rivers under the direst conditions, to rummaging through deserted wagons and finding just the right amount of goods to survive until I pass through the next fort, only to all die of cholera or a gunshot wound or drown or get stuck in a stampede. And then the cycle starts back again. That is, if I want it to.

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