The Oregon Trail series is one of the most well-recognized game series of all time – probably because of the number of grade-schoolers who had to try leading their own caravan through the west in their Social Studies class. The game has seen many iterations over the years, the most well-known of course being the first 2D Oregon Trail title for the Apple II.

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The series comprises educational game that aim to help players understand what it was like to travel the dangerous caravan trail back in the 1800s. They have spawned many memes over the years, and are still used in classrooms even today. In 2021, there is actually set to be a new entry in the series produced by Gameloft. With the new game coming soon, here's a timeline of the series thus far.

8 1971 – The Oregon Trail Text-Based Game (Text-Based)

The first entry in The Oregon Trail franchise was a text-based game released in 1971. Don Rawitsch, an 8th-grade teacher, used the game to teach the subject of the pioneers' travels across North America to his students. Funnily enough, he deleted the source code after printing it out when the class concluded.

Years later, Rawitsch was hired by the Minnesota Educational Computing Consortium to develop educational computer programs. He re-typed out his initial source code, and updated some events and chances for things to occur. The game found its way back into the classroom through the MECC network in 1975.

7 1985 – The Oregon Trail (Apple II)

The 1985 version of The Oregon Trail was a new update for the Apple II that changed a lot about the original text-based adventure. It added visuals to the text-only game, which gave Oregon Trail some of its most iconic and well-recognized art.

It didn't change the central premise of the game, which was still essentially a text-based adventure with the aid of visual cues. However, it was a lot more playable for general audiences, and was released multiple times over the next decade.

6 1995 – Oregon Trail II (Mac/PC/DOS)

The Oregon Trail II was a huge update for the game not just visually or gameplay-wise, but also socially. The original game put very little emphasis on the role of minorities and women in aiding the efforts of the Oregon Trail travelers. With the aid of a Doctor of American Studies, developers updated the game for historical accuracy.

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In The Oregon Trail II, the game's graphics got a massive upgrade too. The game didn't have cartoony early pixel art for its visuals. Instead, it had nearly photo-quality images of real people.

5 1997 – Oregon Trail 3rd Edition (Mac/Pc)

The Oregon Trail: 3rd Edition was another huge upgrade for the game. Instead of just a text-based game with still images, it was now a multi-choice adventure with full-motion video sequences. For students in 1997, this certainly added a layer of realism to the game.

It added many more decisions and "forks in the road" than The Oregon Trail II, such as the ability to gather herbs. It even came with a guidebook that gave cheats to players who were struggling to survive. However, it was far from the final stop on the road for the franchise as a whole.

4 1999 – Oregon Trail 4th Edition (Mac/Pc)

The fourth edition of The Oregon Trail didn't change the formula much, especially compared to the major improvements that the third edition and The Oregon Trail II offered. What it did have, though, was closer attention to historical accuracy and the incorporation of other subjects and partial 3D.

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Where the previous Oregon Trail games focused entirely on history, The Oregon Trail: 4th Edition educated players on some other subjects, too. Additionally, when the player reached a settlement, they could both see a full-motion video and explore the town in a 3D space.

3 2001 – Oregon Trail 5th Edition (Mac/Pc)

The Oregon Trail: 5th Edition was the last entry in the Oregon Trail series developed by The Learning Company. The fifth edition introduced a few minor graphical improvements, like animated river crossings and other events. It also added a sort of story mode.

The story mode followed three children and a man named Captain Jed Freedman, who was traveling the trail to search for the children's father. This story brought in a lot of extra historically inaccurate events, though, like the Donner Party and the Gold Rush happening during the trip.

2 2009 – The Oregon Trail (DSiWare)

After many years without an entry, the Oregon Trail series finally saw a rebirth on the Nintendo DSi store as a downloadable game. This game was a near-complete overhaul of the original game, with cartoonishly stylized graphics and many new paths to take on the trail.

The game was popular on the DSi and spawned two sequels – Gold Rush and American Settler – both of which are playable on mobile devices. This version of Oregon Trail was developed not by The Learning Company, but by mobile games specialists Gameloft, who made the two sequels free-to-play with paid benefits: a bit historically inaccurate, to be sure.

1 2011 – The Oregon Trail 40th Anniversary Edition (Wii, 3DS)

In 2011, the Oregon Trail series officially turned 40. To celebrate the anniversary, a new fully-3D Oregon Trail was developed for the Nintendo Wii and 3Ds systems. Just like every other entry in the series, the game was a survival-focused adventure, albeit with a little bit of artistic license.

The game was very customizable from the caravan to player choices. Many considered it a decent game on launch. However, while The Oregon Trail was revolutionary decades prior, the game wasn't a financial success. It couldn't compare to other top Wii and 3DS games released around the same time.

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