Yes. Seriously. An MMORPG based on that hit edutainment game from MECC, "The Oregon Trail".
So, it would probably start out with you at your local GameStop (in real life. right now I am describing you obtaining said game. this does not take place in game.) browsing through the racks. EverQuest? Too lame. World of Warcraft? Too mainstream. Then, a box suddenly catches your eye. On the front: "THE OREGON TRAIL MMORPG (title to be finalized)". Memories come back from times of the 80s/90s, of playing games on Apple IIs- games designed to teach, yet entertain.
I guess I should clarify something- this game would probably not be as educational as the rest of the Oregon Trail games. It would probably be less "edu" and more "tainment". entertainment.
So, you decide to buy it, and take it home. You pop the CD/DVD in, and install it. Then, you load 'er up. Then: WOAH! A giant splash screen with the "THE OREGON TRAIL MMORPG (title to be finalized)" logo on it, and below that some wagons and some oxen rendered in stunning 3D. This is not The Oregon Trail of days gone by!
After your mind is blown away by the title screen, there'll be a bit of loading time for your brain to recover. Then there's a bit of time while the computer connects to the servers (which should be in Oregon, just for the fun of it) to let you prepare your mind for what is to come.
So once that's over with, you'll arrive at the main menu. You could set your crazy options (including configuring your joystick for ease of use when steering your oxen, or enabling surround sound for the full "THE OREGON TRAIL MMORPG [title to be finalized]" experience), or more likely, select "CREATE NEW CHARACTER" and create a new character.
Now, unlike Oregon Trails of days gone by, you do not automatically get a party. In this game, you have to start out alone and find party members to venture with you! (You could go it alone, but if you die of cholera, it's almost guaranteed that someone else will steal your stuff from the unattended wagon.
So, when you choose a character, you can choose to be either a chick or a dude, and choose your class. It'll be the standard Oregon Trail occupations; Bankers, Doctors, Merchants, Blacksmiths, Carpenters, Saddlemakers, Farmers, and Teachers. As in the original games, some (like bankers) would start off with more money, but others with less money (like teachers) would level up faster. (There would also be the appropriate stat bonuses, such as Doctors having a +5 to Not Dying, while Farmers would have a +5 to Oxen Not Dying.)
So once you create your character, you then enter the game, in good old Independence, Missouri. This would serve as a tutorial area where you learn all the awesome nuances of the game. You'd get schooled in the basics of Buying Stuff, Not Dying, Steering Your Wagon, Hunting for Food, and People Skills.
Once you're done the tutorial, you'll be presented with a wagon, 2 oxen, and some supplies. This'll be the basics that you need to navigate around and Not Die (hopefully). You can walk around Independence if you want, looking for other players to join your party, or you can head out by yourself.
Now, you may be wondering right now, "Won't this game be monotonous? I mean, all you're doing is travelling the Oregon Trail!" Well, that's not what's going to happen, so shut up. The majority of the game will be based upon missions/quests, which will involve transporting stuff, or rescuing people, or other tasks.
But, after much tasking and leveling up, you will eventually be deemed worthy to... TRAVEL THE OREGON TRAIL! The ultimate journey of the game, it will take all of your experience and trailiness to venture this hallowed trail. And once you do, you get to be immortalized on the List of Legends!
After that you get some special recognition thing/status and you get to do more quests and stuff. Or you could purchase the next expansion pack: "THE OREGON TRAIL MMORPG EXPANSION QUEST PACK (title to be finalized)"!