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Arguably the most classic of classic computer games. The best version will always be the original DOS release.

It's fun to name everyone in the party after people you don't like, and then just send them off with a bunch of oxen and nothing else, especially not food.
Jack: Damnit! I tried to ford the Snake River and all my fucking oxen and half my party died!
Jill: Well, how deep was the river?
Jack: Something like 36 feet at the center. That's shallow enough to ford, isn't it?
Jill: ...
Jack: Right?
Jill: ::smacks yo silly ass::
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An originally apple computer-based game by MECC, that any current college-age person surely played as a child, as far back as on a green-tinted computer monitor
Sweet... today we get to play Oregon Trail in computer class!
by sloops March 10, 2005
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Oregon trail is used to describe the trail of hair that leads from a persons chest to their gentials. This is similar to a happy trail but the person is from Oregon.
Jason really needs to trim his Oregon Trail if he ever wants me to blow him.
by Eld Fen November 1, 2018
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To journey over dangerous or rough terrain weighed down by provisions
We live across the street from the supermarket, so instead of driving, my roommate and I usually Oregon Trail our shopping cart full of groceries back to our apartment, dodging rush-hour traffic.
by emrysaki January 13, 2009
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While slamming a girl in the ass, pull out as soon as her crap is comming out.
Drag your dick from her anus, through her ass crack, between her tits and to her mouth, while making sure you leave a solid trail of shit over her body.
Celebrate the end of the journey with a rough deep throat.
"I gave Sally the good old Oregon Trail last month, but she died of cholera after the journey."
by ColonelPrittius March 21, 2018
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The act of snorting Cocaine down a torso, drinking a belly shot, then preforming Oral Sex on a partner with a known STD in one continuous act.
I have Herpes now from walking the Oregon Trail with a stripper.
by Pongluver January 24, 2010
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As an out of state resident, the first line of legal cocaine you insufflate upon your arrival in Oregon.
Yo I blew a massive Oregon Trail after crossing into Oregon for the first time in 2020. So tweaked rn.
by C Chaotic November 13, 2020
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