The Oregon Trail is a classic bit of Americana, and while the actual event was grim, dark, and steeped in the mistreatment of Native Americans, it did launch a rather fun series of games named after it.

Much like Red Dead Redemption, The Oregon Trail series is an idealized look at the exploration of the American West. The Oregon Trail series started all the way back in 197!. It was developed by Gameloft and the Minnesota Educational Computing Consortium or MECC as an educational text-based strategy game.

Over a decade later, in 1985, they would go on to release The Oregon Trail, this time with primitive pixel art graphics of the time. It wasn’t for another decade until they released the version of the game I’m familiar with The Oregon Trail II in 1995. The 3rd edition would come out in 1997, the 4th in 2000, and the 5th in 2001. Later in 2009 a mobile and more cartoonish version would come out yet stay somewhat true to the strategic and educational goals of the series; however, in 2011 The Oregon Trail: American Settler would come out as a mobile, freemium game with mostly no relation to the original series gameplay and style, and deserves no further mention. Aside from a few minor mobile spin-offs, Gameloft recently released a brand new version of the game with some amazing graphics as seen in the trailer below.

Way back in 2005, my elementary school had a rather elementary computer lab in one of the classrooms. Get it? As a nerd, I loved to hang out there at lunch and play some of the old games that the teacher had installed on the computers for the kids. One of them was The Oregon Trail II, and man did I play that a lot. I was also really bad at it since I was like eight or nine. The game was pretty fun for a kid who didn’t have access to a computer, Gameboy, or console yet. It was also the only game I was allowed to play for years that allowed me to shoot a gun.

Looking back at it, I’m pretty sure the reason I lost so much was that I kept on hunting, therefore wasting bullets and supplies, which then led to the wagon being overloaded with meat. But the hunting areas were cool to look at and you got to shoot a gun, which, in an era before Call of Duty, was rare, especially as a school game.

Aside from the shooting and hunting though, The Oregon Trail series was the original X-Com. You got to name your family members and friends and take them on a trip with life or death stakes. It was always funny to see yourself once again falling to a snakebite or some strange disease. A huge draw of the game was the role-play of it all, especially for a group of kids crowded around those blocky old Windows PCs, all playing one journey together. No wonder they go on to play D&D.

The Oregon Trail series is a classic bit of video game history that true connoisseurs of the classics should at least play through a few times; if only so they can brag about it to their friends and random people online.

The Oregon Trail 1st-5th editions are available on Classic Mac OS and Microsoft Windows.