Oregon Trail: the RPG
Each player takes on the role of a family member and works together to try and complete various encounters. Fill the roles of Father, Mother, or Child(er), and choose from classes such as Banker, Woodworker, Fjorder, and Dysentery Dier. In this harsh, gritty campaign, survival is the utmost as the PCs struggle against an uncaring wilderness to complete their quest with their family in tact.
Wait... that sounds awesome. nevermind!
Oregon Trail: The MMO.
why settle for a paltry 30 minute simulation of the hardships when you can navigate a series of challenges and minigames on a time scale comperable to the actual journey? Level up through the journey, collect epic gear such as Shirt of Clothening, Boots of Mud Repelling, and The Buffalo Slayer. When your done leveling up on the journey, switch gears to complete the "Raid Content" of actually living in oregon and running a business. If you're eager to try again, roll an alt by clicking the "Send mail to your cousins" button.
damnit, I would play that too!