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16 of the most hilarious moments in ‘Oregon Trail’

By / 12.12.12

Whether it was on a floppy disk or a CD-ROM, in school or at home, the 16-color game or the stunning (mid-90s stunning) 256-color version, we all remember playing Oregon Trail. It was a perilous adventure game, simple and linear but with enough strategic nuance and randomized events that it could keep any kid entertained for years of play. Looking back on it, though, the game was actually pretty hilarious. Let’s go on a trip down memory lane with some of its funniest moments. What was one of yours?

Photo credit: YouTube

16 When You Spun Around in a Circle Holding the “Shoot” Button While Hunting

Shooting Wildly

The Knowles Gallery, Flickr


…and you didn’t hit a damn thing. What did you expect?


Photo credit: The Knowles Gallery, Flickr

15 When You Set the Pace to “Grueling”

Grueling Speed

Horia Varlan, Flickr


…giving your family what was basically a death sentence just so you could make it to the West Coast sooner.


Photo credit: Horia Varlan, Flickr

14 When You Shot a Squirrel With a Ball Bearing That Was Larger Than the Squirrel

Squirrel

Dominic’s pics, Flickr


…if you had fed that to your family they’d be shitting out pewter fragments for weeks. Don’t do it, no matter how in the mood for squirrel you are tonight.


Photo credit: Dominic’s pics, Flickr

13 When You Actually Made It to Oregon

Oregon Sign

OregonDOT, Flickr


…and realized it was just a bunch of hipsters and shitty weather.


Photo credit: OregonDOT, Flickr

12 When You Chose to Start Off as a Rich Banker

Banker

Clearly Amibiguous, Flickr


…and then watched as your family died while on your journey because you lacked the skills to do anything but make and spend money.


Photo credit: Clearly Amibiguous, Flickr

11 When You Brought 200 Pounds of Meat Back to Your Wagon

Meat

arnold | inuyaki, Flickr


…because who the fuck was going to eat that much meat? Grandma?


Photo credit: arnold | inuyaki, Flickr

10 When You Got Typhoid and Cholera

Cholera Grave

foxypar4, Flickr


…and you were probably like, “Okay, let me just whip out some antibio-waaaaaait a minute, those haven’t been invented yet! I suppose we’d better just dig a grave…”


Photo credit: foxypar4, Flickr

9 When You Had to Ford the River

River

goingslo, Flickr


…and that shit just couldn’t be forded. Not even if you were Harrison Ford. That’s right.


Photo credit: goingslo, Flickr

8 When You Found an Abandoned Wagon

Wagon

Horia Varlan, Flickr


…and were more happy about finding supplies than sad that the missing family had probably been scalped, eaten or sold into slavery.


Photo credit: Horia Varlan, Flickr

7 When Everything was Going Really Smoothly

Smoothly

seanmcmenemy, Flickr


…because you knew something amazingly fucked up was not far from happening.


Photo credit: seanmcmenemy, Flickr

6 When You Were Attacked by Bandits

Native American

lindsey gee, Flickr


…and by bandits what they really meant was Native Americans and by Native Americans what they really meant was Indians and by Indians what they really meant was Injuns. Racist.


Photo credit: lindsey gee, Flickr

5 When You Smacked into a Rock While Rafting Because You Zigged When You Should’ve Zagged

River Rocks

Stanislav Vitebskiy, Flickr


…and it’s that much worse because no one signed up for that shit in the first place. It’s supposed to be Oregon Trail, not Oregon Class VI Whitewater Rafting.


Photo credit: Stanislav Vitebskiy, Flickr

4 When You Found Wild Fruit

Wild Fruit

crabchick, Flickr


…that gave you an even wilder bout of dysentery, promptly destroying your insides and killing you.


Photo credit: crabchick, Flickr

3 When You Caulked the Wagon

Caulk

ephidryn, Flickr


…and FLOATED IT ACROSS A RIVER. Forgive me, but I thought wagons filled with thousands of pounds of buffalo meat were denser than river water.


Photo credit: ephidryn, Flickr

2 When You Broke an Axl

Wagon Wheel

OregonDOT, Flickr


…because where the fuck are you going to find an axl in the middle of a canyon? Also, what’s an axl?


Photo credit: OregonDOT, Flickr

1 When Someone in Your Group Managed to Die From Dysentery

Outhouse

Jim Bahn, Flickr


…because life without Imodium was rough.


Photo credit: Jim Bahn, Flickr


TAGSArbitrary Rankingsfeaturedfunny moments in video gameskids video gamesListsOld school video gamesOregon TrailOregon Trail computer gameOregon Trail gameOregon Trail momentsOregon Trail nostalgiaOregon Trail onlineOregon Trail video game
Jason Epstein
About Jason Epstein... Jason Epstein is a nationally published freelance writer living in the greater NYC area. He's known for his close friends/good conversations/playing bass/wind in the face/rocking out/reading up/holding it down/good times/turning on dimes/and sometimes trying to rhyme(s). He can be reached at his website and you can follow him on Twitter here.

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