

Each skill can make good events more likely to happen, and bad events less likely to happen. The more important the skill is, the more it costs. The player chooses skills with a 120-point limit. After selecting an occupation, the player can select various skills. Also, they may select how many others are with them in their wagon, along with their names and ages. When players start a new game, they can choose their name, occupation, level, date of travel, their starting point and destination, and type of wagon. In addition, events such as diseases (including dysentery, measles, cholera, and others), obstacles on the path, accidents while traveling, and even interactions with other groups in one's wagon train involve being directed to choose a course of action from a set of multiple choices.

Oregon Trail II 's graphics are considerably more detailed than those in the original.
