In this strategy game, players assume the role of a wagon leader on a side-view journey of the historic migration route used by settlers, farmers, ranchers—Americans. Inspired by the real-life Oregon Trail, the game allows players to make strategic decisions to ensure the safety of their party (in most cases, a family) along a sometimes perilous path. Bears may attack, snakes can bite, robbers will loot, and diseases do come ("You have died of . . ."), but the hardened traveler is expected to overcome these unfavorable events to reach the promised Pacific Northwest. If disease or injury is left untreated, family members will fall to the ground and die, leaving headstone icons in their wake.
The game is also punctuated by task-based mini-games (e.g., berry picking, gold panning, rafting, fishing), which can include the hunting of animals. These depictions are minimal—squirrels and rabbits that are shot will turn into icons of meat—and consistent with the game's overall cartoon-like graphics, a feature that mitigates the starker aspects of the game (e.g., dying of cholera, typhoid . . . of dysentery). Along the way, players may encounter a Native American who offers to heal a child's illness by blowing smoke from a peace pipe into the face of the afflicted. The depiction is not gratuitous, but then, secondhand smoke was probably less the issue circa 1848. Dialogue leaves a trail, and may contain references to bathroom humor (e.g., "I poo'd my pants" and "Dung Da Dung-Dung Dung! Buffalo chips are a great source of fuel.").