Oregon Trail is an educational game designed to make students realize they will fail at everything.
Setting out from Independence, Missouri, you see a land of infinite opportunities. And typhoid. And wagon tipping. And buffalo carcasses. But that doesn't stop you. Oh no, you're in it to go someplace new, settle down, and make a new life for yourself. If only it were that simple. The game allows you to choose a starting profession: Farmer, Carpenter, or Banker. What you pick determines your starting money. However, the more starting money, the easier it is for you and thusly, you receive fewer points at the end of the game. After you decide, you go to ye olde General Store, and procure the supplies you require for your journey west. You'll need food, clothes, ammunition, wagon parts, ammunition, food, and ammunition. After you've finished, you'll be on your way! Rations filling? Check. Health Good? Check. Food: A shit ton of it. So, you've begun. You're a pioneer, damnit! And you're going to conquer the west...until you make one bad choice and all of the stuff you bought is lost or destroyed. For example, the Kansas River. Caulking and Floating is a bad idea here. Especially when you lose, oh, 800lbs of the 1000lbs of food you had prior to this lesson in God's loathing of his creation.
God...DAMNIT. Thank goodness you brought ammunition! YOu can hunt for more! Yippie-Kiyay! You sneak slowly through the brush. Your boots make nary a sound as you sneak up on your prey. Just kidding. Real hunters stand straight up, can only face in one of 8 pre-determined directions, and were all crippled at birth and have the inability to walk. Which is quite unfortunate as the game has a tendency to surround you with bushes while hunting. Because not being able to hunt is why you bought the ammo.
Since nobody else came with him, he can only bring back two legs and maybe some fur or something.
Don't worry, you'll lose most of it later when you try to ford a river that's knee high. The rest of the game is basically this:
...But with different landmarks. But it's totally worth getting to the end.
So full of win.