http://www.virtualapple.org/oregontraildisk.html
Warning: It's more IE-friendly than Firefox friendly, for users of that browser.
Edit: But wait! There's more! Really, there's more.
http://free-game-downloads.mosw.com/abandonware/pc/educational_games/games_n_r/oregon_trail_deluxe.html
For the record, I haven't been able to try this one yet, cause I'm at work, but I will try it as soon as I get back to my room.
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