The first game was originally developed by Don Rawitsch, Bill Heinemann, and Paul Dillenberger in 1971 and produced by the Minnesota Educational Computing Consortium (MECC) in 1974.

The original game was designed to teach eighth grade schoolchildren about the realities of 19th-century pioneer life on the Oregon Trail.

In 1971, Don Rawitsch, a senior at Carleton College in Northfield, Minnesota, taught an eighth grade history class as a student teacher.

[1][2] Rawitsch recruited two friends and fellow student teachers, Paul Dillenberger and Bill Heinemann, to help with his student-teaching project.

Then, he modified the frequency and details of the random events that occurred in the game, to more accurately reflect the accounts he had read in the historical diaries of people who had traveled the trail.

[5][3][6] Rawitsch published the source code of The Oregon Trail, written in BASIC 3.1 for the CDC Cyber 70/73-26, in Creative Computing's May–June 1978 issue.

The new version was also updated to more accurately reflect the real Oregon Trail, incorporating notable geographic landmarks as well as human non-player characters with whom the player can interact.

The game has received a major update, in which the player uses trading and crafting to upgrade their wagon, buy food, and cure ailments.

[29] In 2012, a parody called Organ Trail was released by the Men Who Wear Many Hats for browsers, iOS, and Android, with the setting changed to human survivors fleeing a zombie apocalypse.

Challenges were based loosely on the game: hunting for game was done by shooting Nerf guns at college students wearing wigs and cloth antlers, while carrying 200 pounds (91 kg) of meat became pulling a 200-pound man up a hill in a child's red wagon while he recited historical meat facts and pointed out choice cuts.

[35][36] In October 2024, Apple Studios acquired the rights to the film, with a script co-written by the Lucas brothers, and Max Reisman.

The 2021 version of the game for Apple Arcade attempts to "better depict Native American perspectives" and to acknowledge that for Indigenous peoples colonization "was not an adventure but an invasion".

Oregon Trail creative director Jarrad Trudgen, a white Australian, consulted with several Indigenous scholars in an attempt to remove stereotypes and historical inaccuracies.