I remember playing Oregon Trail in grammar school on what I believe was an Apple II, but honestly, I have only a vague recollection of the game. I recall having fun with it, but can't really remember concrete details.
Thing is, I could relay pretty much every detail of the game Black Belt (a game I was addicted to at the time), but my mind's eye is coming up short on Oregon Trail images.
I think this has less to do with the quality of the game or my brain's memory capacity and more to do with the setting. I've forgotten pretty much everything I ever learned in grammar school (mostly on purpose). As such, I wouldn't be surprised if my Oregon Trail memories were a part of the cognitive wipe I experienced since it involved learning new things and stuffs.
Still, I'm looking forward to trying the iPhone version of Oregon Trail coming from Gameloft. Judging by the newly released screenshots, the game looks to be a conversion of the Mobile version of the game, with a larger color palette and tweaked graphical style (looks more Anime-ish). In addition, expect eight minigames, some using the accelerometer, including hunting, fishing, wagon repairing, river crossing, rafting, telegraphing, gold panning, and berry picking. This is exciting stuff.
No release date has been announced as of yet.