The gameplay is from the 1978 version, thanks to JMFSpike for the correction
The Oregon Trail is a computer game originally developed by Don Rawitsch, Bill Heinemann, and Paul Dillenberger in 1971 and produced by the Minnesota Educational Computing Consortium (MECC) in 1974.[1] The original game was designed to teach school children about the realities of 19th-century pioneer life on the Oregon Trail. The player assumes the role of a wagon leader guiding a party of settlers from Independence, Missouri, to Oregon’s Willamette Valley via a covered wagon in 1848.
you can download the emulator here:
or
just launch the boot file and select the game with “j“
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