Until recently I knew precisely two things about Oregon. The guy who created The Simpsons is from there, and it’s in the Northwest United States. I’m from the Northeast of England, but they say the US and the UK mirror each other (I swear I’ve heard someone say that), and I like The Simpsons. Surely then, I’m perfectly qualified to compile the definitive ranking of every version of The Oregon Trail ever made.
I did play at least one version when I was younger, but recently devoted a few weeks to diving into every version of the most famous edutainment game of all time. The series has sold over 65 million copies in total, and is one of the most popular, important, and definitive PC games of all time. Originally published by the Minnesota Educational Computing Consortium as an educational tool for schools in Minnesota, it was so popular it became a breakout hit, sold around the world across PCs and a variety of other platforms down the years, and spawned spin-offs like The Yukon Trail and The Amazon Trail.
Number of entries: 12
What’s included: (Almost) every standalone edition of The Oregon Trail which received an individual release, plus one wildcard.
What’s not included: Games across different systems (several editions came on both Mac and Windows) are only included once, and we couldn’t find a playable version of the actual original 1971 anywhere (I sadly don’t have a mainframe and teletype handy). Oregon didn’t get an official release until 1975.
I played each version of The Oregon Trail twice, or just once if I managed to complete the trail the first time around, with two exceptions. The rankings are mainly determined by the design itself, but if I had a particularly good or bad experience on the trail, then that will change things up a bit too. Nobody has a good time with dysentery.
12. The Oregon Trail 40th Anniversary Edition (2011)
We’re not off to a great start here, but this game is a Wii exclusive and currently out of circulation so I wasn’t actually able to play it myself, unlike the rest. I have been able to find footage of enough people playing, though, to determine this might be the worst and most unnecessary game on the Wii, which is saying something. It has all the basic beats of the proper structure, but is visually murky, many motion controls appear janky—used for completely the wrong tasks—and incredibly boring, and everyone who played it complained repeatedly about how awkward it was to operate.
I might have felt different if I played it, but probably not.
11. Oregon Trail 2 (1995)
Mac OS7, Windows 95
Did… did this pass for fun in 1995? I was two in 1995, so what passed for fun was eating mud, but I still think that would be preferable. The developers were obviously eager to show off technological advancements, so you can walk around towns and settlements for the first time here. In previous games you relied on typing or clicking to trade, rest, or talk to people. The ‘walking,’ however is just agonizingly slow clicks either left or right searching for the store you want. I also met the same NPC several times, a weird guitar-playing man constantly sat on a barrel, even if I met him in the middle of a field.
I assume my character, greenhorn banker Jon, either died before the game started and the whole experience was a fever dream, or else this guitar player was waiting to murder me but was robbed of the chance when I succumbed to disease.
10. The Oregon Trail (1975)
CDC Cyber 70
Type BANG – BNAG
That’s pretty much my experience with this one, which was the first created at MECC by programmer Don Rawitsch. For a few years, the original 1971 code only existed on a printed out stack of paper, before Rawitsch added it to a MECC mainframe. It proved so popular that it eventually inspired the 1980 Apple II version.
This was actually the first one I cleared on my first try, but it didn’t feel particularly satisfying. I didn’t always know what I was doing, yet never really encountered any hardships. I mean, a kid died on me, but other than that, it was pretty smooth sailing. The game is literally all text, so it’s a bit hard to get to grips with. I’m not saying I have the mind of a child who can’t follow a story unless there’s pictures, but I’m also not not saying that. It’s obviously held back by technical limitations, but that doesn’t change the fact it’s not particularly fun or challenging.
This one predates the game many of us would actually think of as the ‘original’ Oregon Trail, and it just feels too stripped-back and basic today despite its influence. I’m sure it was impressive back in 1975, but I’m not ranking them in 1975, so… what are you gonna do?
9. The Oregon Trail HD (2010)
This is a mobile game which has been pulled from the App Store, so I technically haven’t played this one but I did watch a full Let’s Play of the journey, so feel confident enough to put it on the list. It’s basically a lot of those annoying mobile minigames you see advertised while you’re waiting for your own annoying mobile minigame to load, with some Oregon Trail flavor in there. You can shake your phone to pan for gold, steer the cart through a river to collect coins, hammer nails in a rhythm, and a lot of other nonsense.
8. The Oregon Trail (1980)
This plays almost identically to the 1975 version, except the BANG BNAG minigame is now a click-to-shoot effort, and there is a little cartoon wagon which shows your progress along the trail. It’s still more basic than what we know as the OG, but at least the hunting game shows some ingenuity. You can’t aim, you just shoot down the middle of the screen as an animal runs past. It asks you at the start how good a shot you are, and being a better shot literally makes the bullets faster for some reason, but also means you get less actual time to hunt, to try and balance things out. It’s a smart, outside-the-box approach for the time, but the more modern versions don’t need to be nearly so clever to get by.
7. The Oregon Trail 5th Edition (2001)
Mac OS8, Windows 98
Big Zelda CD-i energy with this one. It’s very similar to the fourth edition, but the improvements it tries to make on its predecessor just make it seem a bit worse. The game’s strengths are all true of the 4th Edition too, so I’ll tackle those in a later entry, because this one adds some notable weaknesses. The Oregon Trail games slowly accrued voiceover, green screen performers, and single-character cutscenes between the 2nd and 4th Editions. The 5th Edition adds full-on animated cutscenes to the pile. They are bad.
Sure, there’s a bit of the Saturday morning cartoon charm about them, but they flick between actual animation and still frames with awkward voiceover. There are some atrocious character models. And just generally, they’re clearly lacking enthusiasm.
6. The Oregon Trail (1991)
Another journey westward I was able to complete the first time around. This one got off to a bad start when I typoed my name and accidentally named my settler Staxey. Then, in my first week, my wagon tipped in the river and the game told me I had lost “2 oxen, one set of clothing, 843 bullets, and John, who drowned.” In that order.
The game suspected John would be the least important thing to me, and it was right. I enjoyed the fact you could pick up supplies from other wagons. The second half of the trail is, in theory (and in most other versions) the most difficult part, but it went over without a hitch. Maybe it was because Staxey was a Doctor, but illnesses rarely affected us, and if they did, we recovered quickly. There was a color version of this game released two years later, so this one doesn’t feel like it offers much in the great Oregon Trail history books.
The Top 5
5. The Oregon Trail 4th Edition (1999)
Mac OS7.5, Windows 95
Weirdly for a game made in 1999, just as the ’90s were ending, this version felt the most true to my memories of ’90s PC gaming. Rather than just reading what my party thought, each interaction with them came with a short clip, performed by some terrifically over-the-top actors. They were far more entertaining than the 3rd Edition’s click-the-crotch to talk function or the 5th Editions’ cartoons. One even rested on the picture frame he lived in while telling me he was tired—just A+ scene chewing. The graphics looked pretty neat too, and this one doesn’t suffer from trying to be too techy like Oregon Trail 2 did, instead the gameplay felt more involving without trying too hard to move away from the classic typing/clicking. However, it was often incredibly clunky, slow, and generally a little awkward to use. At first I thought this was just the version I had downloaded, but after checking around online it appears that it was always this bad.
The hunting has perspective and scope, and is trickier but in a more rewarding and realistic way. Animals can’t just go off the screen and cease to exist. I died following a broken leg the first time, which feels embarrassing more than anything else, but we made it along the trail the second time.
4. The Oregon Trail (1985)
Despite three editions coming out prior to this one, the 1985 version is the Oregon Trail, and therefore worthy of a special kind of respect. There’s also a lot to like about this version; it’s not surprising that it’s the one that took off. It’s not the smoothest version of the game, but it does so much right that you have to score it highly. It’s not the best version of The Oregon Trail to play today, but it is perhaps still the most well-rounded.
The hunting, however, is maybe the worst of any game in this long lineage. You wander around aimlessly and the animals stick religiously to corners, then disappear forever. BANG BNAG was better than this. Everything else, though, was steeped in charm. From the pixel wagon being pulled by the ox, the robbers who routinely stole single bullets rather than a box, to the gravestone I discovered which read, and I quote, “Here lies andy, peperony and chease.” Wise words to live by. I played this on an online emulator, and that bit of preserved save data has become part of the history of The Oregon Trail itself. I’m giving this one some points in the rankings for it.
One other historical wrinkle: the MS-DOS version of this 1985 Oregon Trail was slightly modified to serve as the basis of the Oregon Trail handheld game released in 2018. The portability is novel, but the already bad hunting minigame is even worse on the handheld’s controls.
3. Travel Oregon (2017)
This isn’t actually an Oregon Trail game, but is a tribute created by the state of Oregon’s tourism department, aimed at highlighting the joys of modern day Oregon. Rather than oxen, bullets, and wagon wheels, your supplies include craft beers, kombucha, and snow chains. You play as a tourist freshly arrived in Oregon, looking to take in the sights of Portland, Mt. Hood, the Willamette Valley, and more. I played as a yoga teacher named Dakota, and was offered some free beers in exchange for working the door and checking IDs. Being from the UK, I immediately let a 19-year-old inside and was promptly fired. It’s an educational game all right.
Travel Oregon’s description encourages you to “keep playing until you win,” but most of the time it didn’t feel like there was a focus. My party and I (Peyton, Cheyenne, Brooklyn, and Jackson, all yoga teachers too) just wandered around Oregon and did stuff. It actually felt like being a tourist, and had significantly lower stakes than a 19th century Oregon Trail, which is exactly how it should be. It’s not a proper Oregon Trail, but it’s very fun, so it’s getting a bronze medal.
2. The Oregon Trail 3rd Edition (1997)
Mac OS7.5, Windows 95
This one is worthy of praise mainly for taking the new ideas of The Oregon Trail 2 and making it much more fun. It doesn’t look particularly different from 2, but it understands its limitations and pushes forward in the right places. The Oregon Trail 2 was the first version which really felt ‘alive’, the first which took the game off point-and-click text based play and into something approaching player agency. It was just far too slow and didn’t understand how to structure a game with that focus. 3rd Edition has learned from those mistakes.
Fishing is a bit boring here, but as a new feature, it’s also a fresh step in the right direction. I feel like it would have been a welcome addition, flaws and all, in 1997. Also, it’s fishing. Being boring is surely part of the appeal, right? The textbook presentation style is a little bland, though. The 3rd Edition is desperate to show you real images when the pixel cartoons have much more charm. The most memorable thing about this game is its actors.
Most dialogue scenes were fully acted out, with over-the-top gestures in front of a green screen. The only issue is they’ll stop halfway through a sentence, waiting for you to click to continue, which seems to negate the point of having an actor do it. Also, because clicking their limbs and heads didn’t always work and they were often in the background, I found myself clicking their crotch to get them to continue. I can’t decide if it should lose or gain points for that.
1. The Oregon Trail Deluxe (1992)
This was the first version that I played for this incredibly scientific ranking, and I think it’s the best version even though on my very first run three of my party died on consecutive days. Actually, sort of because they died. When I started playing these games to rank them, I was not very good at The Oregon Trail. My rankings are based entirely on my own experiences, and perhaps a better player would rank them differently. I kind of knew I’d be in for a lot of death, though, so having three hit me in a row during my first playthrough meant the game immediately earned a place in my heart. For me, a quintessential part of The Oregon Trail is that I suck at surviving it.
The hunting minigame plays really well in this version, and it all felt mostly intuitive. I prefer the mouse interface to the original’s typing, or the later attempts to make it more sophisticated. The little pixelated animals actually looked like they were supposed to, aiming was fun and challenging enough, there was a good range of animals and obstacles, and the little rabbits zipped across the screen while the big buffalos lumbered. It’s basically just a hunting mobile game by today’s standards, but a pretty good one, and the perfect balance between giving the player real control and making the whole thing too complicated.
As the first version I played, I didn’t really understand everything, and didn’t discover until later that picking Teacher as a profession meant playing on hard mode. After dying, my second run was a Banker and we fared much better, though we still died. Also, I didn’t understand the deal with water here. There was no option to buy, refill, or even check my water. Towards the end of the game I was told I had no water, only to be told days later I now had bad water. Were my settlers… drinking their pee? In any case, I died soon after.
The Oregon Trail Deluxe is a color version of the 1991 game, but it also plays a little smoother, although the ‘bad/no water’ issue didn’t affect the black and white version. I was able to be Stacey rather than Staxey in this one, although I’m not sure if that was an improvement. But Deluxe strikes the right balance between ’80s and ’90s Oregon Trail. If you’ve got to die on the trail, make it this one.