Oh, doesn't the game's name bring you back? I remember playing it for the first time in a school computer lab, naming my party members ridiculously, buying a ton of food, and setting out at top speed across 2,000 miles of unforgiving trail, only to drown in a river or die suddenly of dysentery. Yes, the game and all of it's iterations, Oregon Trail II being my all time favorite, remind me of a simpler time, so I revisited the old game on an emulator on my modern computer. As expected, it's still a great game, and has endless replay value (will I die of an accidental gunshot? Rabies? Smallpox? Who knows?!)
Anybody who has played knows that the game represents a very real time in American history. Pioneers setting out on the Oregon Trail or Mormon Trail probably didn't invest as much money in bacon as I did, and definitely didn't mess around choosing the right draft animals and clothing. No, the real Oregon Trail was more of a life or death situation. Sure, you can hit 'restart' if you forgot to buy canteens and water barrels before you died of thirst in the Forty-Mile Desert, but if you were a real pioneer, something as simple as water could be a major decision. Haul too little, and you and your animals will die of thirst. Carry too much, and you'll slow your wagon train considerably. Rely on water along the trail, and you could catch any number of horrible diseases, chiefly cholera and the famous Oregon Trail dysentery.
We remember the horror stories of the trail, like the presumed cannibalistic Donner Party caught in the Sierra Nevadas during a particularly nasty winter, but not the everyday travelers. The everyday chores of caring for the oxen (or mules, horses, and other livestock, if you were lucky), cooking for the group with minimal supplies, mending clothes and wagons, and keeping watch against thieves are totally unheard of for most people now. But even the humblest trailgoer completed these tasks like it was nothing.
If you're looking for a game that will make you think about history in the everyday sense, I can't recommend it enough.