Along the trail, the player makes choices about supplies, resource management, and the route, and deals with hunting for food, crossing rivers, and random events such as storms and disease.

It is the first graphical and the most well known entry in the Oregon Trail series, and was MECC's flagship product from release until the company was bought by SoftKey in 1995.

They begin the game by selecting their character's profession—banker, carpenter, or farmer—which corresponds with difficulty levels and give different amounts of money with which to start the journey.

An animated ox-pulled wagon is shown, with a representation of the next landmark sliding towards it from the left as the party travels and a landscape of the terrain for that segment in the background.

If the player chooses to hunt, they are shown a minigame where they control a human character that can be moved around a fixed screen containing a randomized assortment of rocks and plants based on the terrain of the segment the party is in.

When the player ends the minigame, they receive an amount of food based on what animals were killed, though a maximum of 100 pounds can be taken per hunt.

[3] In 1971, Don Rawitsch, Bill Heinemann, and Paul Dillenberger developed a text-based strategy video game titled The Oregon Trail for use in the 8th grade history class for which Rawitch was a student teacher.

[2][11] MECC began converting several of their products to run on microcomputers, and John Cook adapted The Oregon Trail for the Apple II; though the text-based gameplay remained largely the same, he added a display of the player's position along the trail on a map between rounds, and added graphics to the hunting minigame.

MECC had moved into this market the year before, hiring programmers to create original software titles for schools and home consumers.

[2] As the game was intended for the home market rather than school settings, it needed to be entertaining as well as educational; Bouchard set as a guiding principle that the entertainment "should arise from immersing the player in a historically accurate experience", and conversely that the educational aspect should arise from that immersion rather than explicitly instructing the player about history.

Each segment of the game had different environmental settings and probabilities, and the traveling periods are composed of some number of days which then act as the unit of time.

[2] The team removed the medicine and doctor system of the original as historically inaccurate, and instead added multiple types of disease.

During the user testing in March 1985, as the "dead state" graphics had not yet been completed by Kapplinger, Shimada instead flipped animals upside down to indicate their deaths; this was kept in the final game, as the team and child playtesters found it humorous.

Bouchard was concerned, as this left the game without a climactic ending, though it would have been difficult to create the entire design at that point in the project.

The team was able to borrow programmer Steve Splinter to develop the rafting portion, and quickly created a much simpler version based on dodging rocks in the river.

Other priorities were including river crossings, for which the team built a system that takes into account the location and weather of the crossing, and adding replayability, which he accomplished by adding a point system with difficult high scores to beat, multiple starting options, and a challenging hunting minigame.

It was followed by a version published for the Macintosh Mac OS 6 in 1991 and DOS in 1992; both releases had altered the game's interface to be controlled with a mouse instead of a keyboard and added simple sound effects and eight different profession options.

[19] In 2018, a variant of the DOS version of The Oregon Trail was released as a physical handheld game by Basic Fun, initially as a Target exclusive.

[22] Matt Smith of Kotaku called it "one of the most iconic and grueling games to hit the classroom computer", and said that the 1985 version was the one "that rose to stardom and eventually spawned countless memes" and "etched its legacy in the memory of a generation".

Even now, there remains a constant pressure to revive the series, so that nostalgic Generation Xers and Millennials can amble westward with a dysentery-riddled party once again.