The Oregon Trail: 5th Edition is a game for players aged nine and up with educational support. It builds on the previous editions of the game simulating traveling through towns and wilderness in the state of Oregon between 1840 and 1860 when over 300,00 emigrants headed west across the United States, with adventure-like gameplay elements. The core game builds on Oregon Trail II and various new features are introduced, and elements from previous editions are added or removed.
The stories of migration are told through the characters mountain guide Captain Jed Freeman and the Montgomery children Jimmy (10), Cassie (13) and Parker (15) who want to find their father. The game also teaches history and geography and complements the social studies curriculum. Other educational elements include math, language arts and logical reasoning. To survive with the wagon players need to balance health, food and financial resources with many decisions to trade, buy or leave supplies to reach Oregon, the Salt Lake Valley or California. Dangers include obstacles, river crossings (with updated graphics), delays and disease. To survive players need to learn how to hunt and fish. Historical facts and maps are collected in the Montgomery Journal and the Oregon Trail Guidebook. The journal can also be printed for offline use.
Compared to the previous editions the biggest novelty is the introduction of the Montgomery family and the way their story is woven into the game. At various points during the journey story sequences are triggered. The children experience events and Captain Jed for instance tells them historically accurate stories at the campfire. Conversation pictures are no longer animated. Plant gathering from the third and fourth edition is carried over, but the Wild Fruits and Vegetables events from the second game about identifying which plants are edible and which are poisonous is not included. It is still possible to look for edible plants when someone has scurvy. The soundtrack from the second edition is removed in favor of a single repeating audio loop.