The game was designed to teach schoolchildren about the realities of 19th century American pioneer life on the Oregon Trail. Players started out at the beginning of the trail, in Independence, Missouri, where they selected a profession for their character from a number of choices such as banker or carpenter. Each profession had different advantages and drawbacks. Players then had to buy equipment, oxes, and food for the journey.
Along the way, numerous events could occur. Friendly or hostile Indians might be encountered; a member of the family might fall ill or die of a snakebite; rivers had to be forded or ferried; and many other events occured. Players usually have several different choices of how to deal with each situation.