The game design is based on Oregon Trail II, but adds various new features to the game, such as the fishing and plant gathering features from the 3rd and 4th editions. Updated graphics have been provided for river crossings. There are also added animated segments which follow the fictional journey of the three Montgomery children, Parker, Cassie, and Jimmy, who leave Independence accompanied by an African Americantrailblazer named Captain Jed Freedman to search for the children's father in Oregon. Various points of the children's story are triggered when the player reaches a certain destination on the trail, which ranges from dangerous experiences to campfire scenes in which Captain Jed would tell a story that reflects other historically accurate incidents. The conversation pictures are no longer animated. The soundtrack of Oregon Trail II has also been removed, replaced with a single repeating audio loop.