Different occupations bestow various bonuses to the protagonist, and are equipped with passive skills, which will influence the rate of success during certain random events and activities. The player is able to choose an occupation for the protagonist, such as banker, doctor, gunsmith, carpenter, journalist, butcher, pastor, artist, and many others. As opposed to one year in the first game, the sequel allows the player to choose between twenty years of travel, from 1840 to 1860. The game also allows the player to create virtual companions for the journey, designating their number, names, and ages. In the beginning of the game players choose their name, occupation, level, date of travel, starting point and destination, as well as the type of wagon. Play Oregon Trail II online! Oregon Trail II game description

The sequel changes, enhances, and adds many gameplay features. The game follows the basic structure of the predecessor, which is a simulation of traveling through towns and wilderness in the state of Oregon, with adventure-like gameplay elements and educational material. Oregon Trail II is a sequel to Oregon Trail.