This was the version of Oregon Trail I played the most, but I only played it in black and white. I'm pretty sure it had local network multiplayer support.
@marekkpie: I don't think his intent is to play it with a race mentality, but rather with an exploration/testing-his-own-memory mentality. I think the idea is to see how far he can get with no tools or outside help and then start referencing maps/guides/etc. when he feels truly stuck.
ildon's comments