Did you play "The Oregon Trail" as a child?

If you did, first refresh your memory with this emulator: (requires a plugin)
http://www.virtualapple.org/oregontraildisk.html

Then, play this version: http://www.thuleroadtrip.com/

It's *so* funny -- really well-done, if not, perhaps, as educational. And none of your party is liable to die of dysentary.