Back in the day, I used to sit in Mrs. Getzlman's second grade computer lab class and play games like Number Munchers and Speedway Math, despising the fact that both games severely lacked any sort of firearms. That's why I was also so pumped when I got to play Oregon Trail. Not only did it have guns, but your friends and family actually died in it. And they did of crazy things like cholera and dystentary. It was heavy stuff for a second grader, but it was also amazing.
Now there's this new game out there created by Thule (they make car racks) that is a pretty close parody of Oregon Trail. It's called Thule Trail and instead of trekking to Oregon in a Conestoga, you take a road trip from Chicago to Santa Barbara. You can still hunt, your friends disappear, and they even added some Atari-style snowboarding, kayaking, and mountain biking. Brought back some major nostalgia for me
It's at www.thuletrail.com. Check it.