Oregon Trail recreates the journeys of the pioneers who traveled across the Western U.S. during the 1820's - 1860's. To a certain extent it is a role-playing game, as players are cast into the role of Trail Boss, responsible for shepherding his party from their jumping-off point to their ultimate destination. Trail Bosses measure success (in relation to the other players) by retaining the highest percentage of the starting wagons, personnel and stock when they arrive at their final destination.

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