We played Oregon Trail on our school computers all the time when I was in 2-3 grade. The only thing the guys played for was the hunting minigame. I remember that one kid was the class badass at that, he would sit for like five minutes and just wait for a bear to hurdle across the screen.
I always preffered the less popular amazon trail though, it had the fishing and the photography minigames and I just found the setting more interesting.