To survive, players must learn to hunt and fish. Hazards include obstacles, river crossings (latest graphics), delays and disease. To survive on a wagon train, players must balance health, food, and financial resources while making many decisions, such as trading, buying, and dropping off supplies to reach Oregon, the Salt Lake Valley, and California. Other educational components include mathematics, language and logical reasoning. The game also teaches history and geography and complements the social studies curriculum. The immigrant story is told through the characters of Captain Jed Freeman, a mountain guide, and the Montgomery children, Jimmy (age 10), Cathy (age 13) and Parker (age 15), who want to find their father. The Oregon Trail: 5th Edition is a game for players ages 9 and up with educational support, a simulation game that takes players on a journey through the towns and wilderness of Oregon between 18, when more than 300,000 immigrants set out for the American West, with adventure-type gameplay elements It builds on previous editions that have included The main game is based on 'The Oregon Trail II', which introduces a variety of new features and adds or removes elements from previous editions.

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