The Oregon Trail: 5th Edition is a 2001 educational game developed by Riverdeep Interactive Learning and published by The Learning Company.
The game design is based on Oregon Trail II, but adds various new features to the game, such as the fishing and plant gathering features from the 3rd and 4th editions. Updated graphics have been provided for river crossings. There are also added animated segments which follow the fictional journey of the three Montgomery children, Parker, Cassie, and Jimmy, who leave Independence accompanied by an African American trailblazer named Captain Jed Freedman to search for the children's father in Oregon. Various points of the children's story are triggered when the player reaches a certain destination on the trail, which ranges from dangerous experiences (e.g., Jimmy is bitten by a snake) to campfire scenes in which Captain Jed would tell a story that reflects other historically accurate incidents (such as the Donner Party, the California Gold Rush, and the Santa Fe Trail). The conversation pictures are no longer animated. The soundtrack of Oregon Trail II has also been removed, replaced with a single repeating audio loop.
The Oregon Trail: 5th Edition is abandonware and no longer sold or supported by its publishers. Files are archived here for these platforms:
Also, I got it to work by setting it to compatibility mode. I’m on windows 7. Check all the boxes for compatiblity, and set to windows XP compatibility. Do this for the “ot5.exe” file, which is separate from the launcher.
Also, you can edit the “oregon5.ini” file so it says “rsrpath=data” and then copy the “data” folder from your installer into the “Oregon Trail 5” folder in program files.
Update: Used an .iso found elsewhere (exactly the same I think) and, after editing the INI file to include the proper path to the data folder as suggested by google, got it to work fine. Mind you this is in Ubuntu using Wine. Still can’t get it working completely in Windows 10, it keeps freezing during or after cutscenes.