The Oregon Trail: Fifth Edition
The player assumes the role of a wagon leader guiding his party of settlers from Independence, Missouri, to Oregon's Willamette Valley over the Oregon Trail via a Conestoga wagon in 1848. The game has been released in many editions since the original release by various developers and publishers who have acquired rights to it.
This is Version 5 of the game that was released for Windows PC's.
I was able to run this on a Windows XP desktop and during some of the video cuts cenes however, the video would freeze and the application would crash, loosing game progress.
You should probably look at setting this up on a Windows 95/98 box for more stability.