Anyone else have a love/hate affair with Oregon Trail? I’m talking the old school version that came on a black floppy disk the size of a placemat with blobs of color vaguely resembling oxen and a wagon. So when Oregon Trail II came out in all its color graphic glory in 1996, I’m sure I wet my seven-year old pants. Unfortunately, I was absolutely terrible at both versions of this game, which meant a step down in the social hierarchy of elementary school (among other reasons. Being bad at Oregon Trail sounds a lot better than “I was that weird girl who played with Hot Wheels and had binders of Pokemon cards” or “I wore the same floral purple leggings and tiger tee shirt everyday.” Curse whoever it was that let me out of the house in that ensemble). Emerging victoriously as an Oregon Trail guru made you a god among men in the third grade. But it was hard! Especially the 1996 versionso many things to decide.

How the heck are you supposed to know how many pounds of flour you need for six months? I was seven. Obviously this meant filling my wagon with 2,000 pounds of bacon was a brilliant idea. Then when all my food went bad after three days, my travelers kept dying of the measles or malaria or dysentery (as this tee points out), or stepping on rattlesnakes and eating poisonous fruit. What a band of loonies. I remember wishing there was a dialogue button so I could yell “Timmy, you idiot. It’s not like you don’t know that’s a rattlesnake. What else has teeth and flails about on the ground making rattlesnake noises?” Obviously, this is still a sore subject. But grade "A" t-shirt material. Photo via


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