Every Version of The Oregon Trail Game, Ranked

The Oregon Trail game struck a chord with gamers over half a century ago, and game development teams have since been remaking the game for new players every chance they get.

As a result, many versions of the game are available for various platforms. You can also play the Oregon Trail game online. Whether you’re looking to get into the game for the first time or want to revisit the game but play another version, you have a lot of options.

We’ve ranked all the versions of the Oregon Trail in order of impressiveness to help you find the version you like best. 

Every Version of The Oregon Trail Game, Ranked

#1 The Oregon Trail 40th Anniversary Edition (2011)

Wii and 3DS

The Oregon Trail game turned 40 in 2011, and to commemorate the milestone, MECC and Gameloft collaborated to create The Oregon Trail 40th Anniversary Edition. 

In addition to hunting, the game required players to drive the wagon for the first time in the series. In addition, the game gave players access to four unique stories, each of which can be played through in three different periods.

Players can customize the wagon, and the random hurdles programmed into the game ensures you have a fresh experience every time you play. While it’s the most impressive entry in the series, it does not enable players to play Oregon Trail online. 

#2 The Oregon Trail (2009)

DSiWare

The 2009 release was a complete revamp of the original Oregon Trail. While the graphics are cartoonish, the game doesn’t feel out of phase from the original.

It featured exciting traveling mechanics, needing players to balance the wagon’s speed when on the move. Move too fast, and you could break the wagon or injure a party member. Move too slow, and the party won’t reach the destination before the winter, making the game more challenging.

The game also features a whack-a-mole type berry picking game, among others. Every minigame has levels, so the game gets more challenging every once in a while.

#3 Oregon Trail 5th Edition (2001)

Mac/Pc

Instead of allowing players to select and name the party members, the Oregon Trail 5th Edition features a story mode. The player must lead the Montgomery family and Captain Jed Freedman on a journey to find the children’s father. 

The game retains a lot of the elements in the original. Balancing supplies is a big part of the game, and there are many obstacles to overcome. Besides delays and disease, the player must master crossing rivers, hunting, and fishing. 

The 5th Edition has maps and historical facts and is arguably one of the more informative games in the series.

#4 Oregon Trail 4th Edition (1999)

Mac/Pc

The Oregon Trail 4th Edition was a big upgrade from its older versions, featuring partial 3D graphics and improved gameplay. Before this game, all the other games in the series were primarily focused on teaching players the authentic history of the wild west. 

This game educated players on various other subjects, which helped with the popularization of the game. The player must lead the party across the map, hunt and fish to survive, and deal with dangers such as stampedes and gunshot wounds.

The 3D travel and 360° panoramic views make it a stand-out entry in the series.

#5 Oregon Trail 3rd Edition (1997)

Mac/Pc

The 3rd Edition of Oregon Trail brought some big changes to the game. This entry in the series changed Oregon Trail from a simple text-based game to a multiple-choice full-motion video adventure across the country. 

The graphics made the game a lot more appealing to the target audience – students – in 1997. Besides, this version of the game added a lot more lore and “forks in the road,” making the playthrough longer and more interesting. The included guidebook had cheats mentioned in it to help out players that were struggling to survive.

#6 Oregon Trail II (1995)

Mac/PC/DOS

Oregon Trail II came out in 1995, after a ten-year gap in the franchise, which was long enough to make the game more inclusive. This version of the game depicted minorities and women in bright light. The development team worked with a Doctor of American Studies for the historical accuracy of the new inclusions.

#7 The Oregon Trail (1985)

Apple II

The Oregon Trail on the Apple II is considered the game that put the series on the map by many gamers. It brought a lot of interesting visuals and now-iconic art to the previously plain text-only version of the game.

The premise and features weren’t much different from the original, but the visual clues and quirkiness of the game made it a game people didn’t want to stop playing.

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

The original game worked on a teletype and mainframe and didn’t have any graphics. It was a passion project initiated by Don Rawitsch, which was brought to fruition with the help of two of his roommates. The trio developed the game to teach a class of eighth-graders about the history of the wild west.