An Evening With Oregon Trail

My first time on the trail was a comedy of tragic events. At the first river crossing one of my party members drowned when my wagon tipped over in less than four feet of water. Tragic, but one less mouth to feed meant my food would last longer for the living travelers. People got sick. Limbs were broken. We got lost. There was fog. There were measles. Then a thief stole some of my oxen. And not just some of them, but most of them. As in, eight out of my ten. Who steals eight oxen?

An Evening With… Is a series of posts featuring games that are relatively small in scale or can be experienced in a short period of time.

Even people who don’t know a thing about video games know about Oregon Trail. Part video game, part learning experience, it’s hard to separate the game itself from its status as a cultural icon. Many people from my generation have memories of playing through the game in school, back when software developers tried to combine education experiences with video games. Perhaps their parents even bought the game for the family computer under the impression their kids would learn a few things from it. My wife has stories about how she and her sister used to play the game together “back in the day”. I was never a part of that crowd, at least not that I can remember. When a cleanup of the home office yielded the game’s discovery on a dusty bookshelf, my wife insisted I play through it.

Starting ShopOregon Trail tries to be a historical simulator. You are the leader of a party that is traveling across the continental United States with the aim of settling in Oregon. You start your journey in Independence, Missouri by picking your profession. Certain vocations lend bonuses that may be helpful over the course of the dangerous journey. A banker, naturally, can afford to buy more supplies at the start of the game. Doctors are more likely to keep their party healthy. Carpenters and blacksmiths have significantly less money to work with, but they can potentially fix their wagon should it break and they will receive a significant score bonus at the end of the game. You can determine how many people you’re taking to Oregon with you. Forewarning: Your party members possess no skills and exist only to fall ill and consume your precious resources out in the wilderness. Once your profession and party members are set, it’s off to the general store to load up on supplies for your wagon. Oxen, nonperishable food, and bullets are the only things you are guaranteed to use; most other things you’re buying as insurance against disaster. The shopkeeper offers advice on what you should buy, but only the trail will show you what you actually need.

My first time on the trail was a comedy of tragic events. At the first river crossing one of my party members drowned when my wagon tipped over in less than four feet of water. Tragic, but one less mouth to feed meant my food would last longer for the living travelers. People got sick. Limbs were broken. We got lost. There was fog. There were measles. Then a thief stole some of my oxen. And not just some of them, but most of them. As in, eight out of my ten. Who steals eight oxen? How could my party even allow such a thing? Did they not notice our only means of transportation mooing as they were led away by someone they’ve never seen before? I’m still mad at that band of traveling idiots. Just after reaching the halfway point of the journey the most tragic thing of all happened: A program crash. Fifty minutes of progress down the drain because I forgot to save my game. I’m not sure what caused the crash; it was the result of either my constant task-switching for the sake of getting screenshots or the fact that I’d been running the game in Windows 95 compatibility mode. I later discovered that I didn’t really need to be running the game in compatibility mode, so lesson learned.

No shopkeeper could have prepared me for this.

For my second attempt on the trail I ensured the game was running flawlessly, including my ability to save both the game and its text log. What follows is a selection of the more interesting highlights from the transcript of my trail journal.

My First Second Journey

March 1, 1848
We started down the trail with:
10 oxen
15 sets of clothing
400 bullets
3 wagon wheels
3 wagon axles
3 wagon tongues
800 pounds of food

Oregon, ho! So we endeavor to leave the wastelands of the Great Plains to endure two thousand miles and many months of hardships for a bette- wait. Why are we going to Oregon again? No, really. I got so caught up in the journey itself that I have no idea why we’re making the journey in the first place.

March 6, 1848
We have arrived at the Kansas River Crossing.

The river makes me afraid. 666 feet across and 10.6 feet deep. Evil lurks here.

March 12, 1848
We have arrived at the Big Blue River Crossing.

At this river I am presented with only two options: ford or float. Neither one appeals to me, and there’s no ferry. At 9.4 feet deep, this river is nothing more than a wet death trap. I’ll wait a day to see if the river drops any. It does. Not knowing how far it’s going to drop, I’ll wait until it starts rising again before heading across.

16 days later, the river is down to 3.4 feet. I think it might be safe to try floating the wagon over.

March 28, 1848
We had no trouble floating the wagon across.
Heavy fog. Lost 1 day.
Mandy has a fever.

My party ate a LOT of food in 16 days. Time to hunt.

March 30, 1848
We shot 1 pound of meat.

13 bullets and all I have to show for it is a pound of… squirrel? Is that what that is?

April 8, 1848
We have reached Fort Kearney.

An old dude said this should be the easiest part of the trail, so I’m opting to pick up the pace in hopes of making up for lost time.

We will now travel at a more strenuous pace.

April 19, 1848
Heavy fog. Lost 1 day.

My overall health indicator has dropped to “fair”, what with a broken leg and the measles and all. A hunting trip and a day’s rest are in store.

April 21, 1848
We shot 5 pounds of meat.

I managed to bag three rabbits as they gleefully bounded towards a beautiful stream. Serves ’em right.
We decided to rest for a day.

April 25, 1848
An ox is sick. Poor Fluffernutter.

Sick Ox

Why is it that the image announcing that an ox is sick makes it look like our only option is to put the thing out of its misery? Seriously, I’m getting some serious Napoleon Dynamite vibes here.

Napoleon Cow

April 26, 1848
We shot 71 pounds of meat. I’m pretty sure this didn’t come from the sick ox. I hope.

May 1, 1848
Mandy is well again.
Woo, we’re all in “fair” health again! Pretty soon we can celebrate by decreasing food intake to scarce rations and increasing to a grueling pace!

May 6, 1848
We have reached Independence Rock.
Aww, they’re circling their wagons under the giant circular rock. How quaint.

Independence Rock

May 7, 1848
An ox died. Good, I guess we didn’t eat him, then.
We decided to rest for 2 days to mourn Fluffernutter the ox.

Dead Ox

May 14, 1848
A thief stole 9 sets of clothing.
A thief stole 9 of my 15 sets of clothing? In a wagon full of food and bullets and spare parts, this dolt goes for sets of clothing? This type of seemingly petty nighttime thievery is what to led to things like the Great Train Robbery. I do declare society is preparing to unravel!


May 17, 1848
We shot 22 pounds of meat.
Why are my bullets so slooow!?!

May 19, 1848
We lost the trail for 5 days.
Ha! Poor guy looks pretty desperate standing in the middle of a field a few paces ahead of his wagon! Oh wait, that’s me. Hmm, I just made myself sad.

Lost Trail

May 24, 1848
We have arrived at the South Pass.
My food stores are a bit on the low side, but I can’t hunt at landmarks because there are “too many people around”? What that really means is this is the only hunting ground where you’re guaranteed to bring something home.

That sounded way more creepy than I intended it to.

Spoiled Food
That looks like way more than 20 pounds of meat.

From here my two options are to go to Fort Bridger for trading or use the shortcut to the Green-River crossing. Since I’m low on food and don’t have much to trade with I’d prefer to try and keep up with a good traveling pace. Time to apply a little math to my dwindling food reserves. 226 pounds of non-perishable food left. Five people eating generous portions eat a pound of food per meal or a total of 15 pounds per day. That’ll last me two weeks. Looking at the hunting limit of 200 pounds of food per hunt, I need to bag at least that much game every four days. Assuming a minimum of four more months of travel time, that’s a total of 1,800 pounds of food I need between now and Oregon. These people eat too much.

May 28, 1848
We shot 1865 pounds of meat but were able to carry back only 200 pounds of meat.

Bison. Slow and huge. A hunter’s best friend. Odd that so many people warned me against hunting them.


June 5, 1848
We decided to rest for a day. These poor people’s health keeps declining to “fair”. Generous portions, steady pace, what more do these wimps want?

June 15, 1848
Mandy is well again. Yay! Let’s have a party with extra rations all around! Wait, we’re already on “generous” portions! What took you so long to get well?

June 17, 1848
Mandy has a fever.
Why are you so sickly, woman?

June 29, 1848
We have reached Soda Springs. This appears to be a meeting place and trading grounds for fellow trail goers. Do I dare try and trade any of my wagon parts for nonperishable food?

We traded 2 wagon axles for 80 pounds of food. Thos axles were worth $20 each, meaning I just paid fifty cents per pound of nonperishable food. The price seems a bit steep, but what’s the cost of starving to death? You know, other than death?

July 2, 1848
We have reached Fort Hall.

There’s a fort with a general store here and it’s literally three days away from Soda Springs? I lost money on that food for axles trade. If I can find that twerp again I’ll shoot him in the leg.

We visited the store and bought:
1 wagon axle
80 pounds of food
1 set of clothing
We decided to rest for 2 days.

July 7, 1848
No grass for the oxen.

Why the heck does everyone’s health drop randomly from “good” to “fair”? Besides the fact that there’s no water and no grass. I haven’t noticed any pattern or cause and effect to it. Where are we anyway?

July 19, 1848
No water.
We have arrived at the Snake River Crossing.

No water at the Snake River Crossing…so does that mean Snake River is dry? How high is Snake River? That’ll be a test of this game’s continuity. 12 feet deep and 1000 feet across. That’s a big river. This game makes no sense.

July 20, 1848
We had no trouble floating the wagon across. Help from an Indian cost us two sets of clothing. That’s the equivalent of forty bucks. I miss the five dollar ferry.

July 24, 1848
We shot 111 pounds of meat.
Look ma, I just bagged a bear!


July 25, 1848
No grass for the oxen.

July 26, 1848
No water.

July 27, 1848
No water.

July 28, 1848
No water.
Why does Idaho not have any water? Maybe potatoes are the cause of all the world’s problems.

We have reached Fort Boise.

August 2, 1848
Kathy has the measles.
“The measles can lead to death, especially among the elderly”. Sigh. If it’s not Mandy it’s someone else. I guess it’s time to take a rest for a few days.

We decided to rest for 3 days.

August 3, 1848
A thief stole 85 pounds of food.

People: this is why we don’t rest.

August 13, 1848
Everyone is in poor health, rather suddenly. What the what. Time to try resting again. If another thief comes I’m going to flip my lid.
We decided to rest for 3 days.

August 21, 1848
We have arrived at the Grande Ronde in the Blue Mountains.
Grande Ronde is quite breathtakingly beautiful in real life. It’s too bad the render in this game makes it look like a pile of irradiated blueberry marshmallow Peeps twinkling in the distance.

Purple Peep Mountains

I’m presented with a choice: Either I can go to Fort Walla Walla to buy supplies or I can take the shortcut to The Dalles. Buying supplies costs money, and I’ll need money to start life in Oregon. Shortcut it is.

August 23, 1848
We lost 41 pounds of food due to spoilage.
Tony is suffering from exhaustion.
We’re all exhausted, Tony.

September 3, 1848
Tony is well again.
Tony looks like a little girl.


We have reached The Dalles. After talking to the locals, it appears I’ll have the choice of floating down the river on a barge or traveling over the mountain. Pixar movies and my first crashed attempt at Oregon Trail have taught me that rivers are nothing more than wet deathtraps, so we’ll be going over the mountains via the Barlow Toll Road.

September 4, 1848
The trail is impassable. Lost 7 days.
This is just another way of saying “we got lost”. That’s how it looks from the picture, anyway.

Impassable Lost

September 14, 1848
The trail is impassable. Lost 2 days.

This toll road sucks. Whatever I paid to take this route, it was too much.

September 20, 1848
We’re approaching the Willamette Valley, which is rather gloriously rendered by Oregon Trail as two lumpy rocks surrounded by some miniature pine trees. I’d hope it’s more impressive in real life.

WV puny thumbnail

September 25, 1848
VICTORY! I conquered the Oregon Trail after 6 months and 25 days of carrying a wagon full of supplies and several other party members of dead weight!

Willamette Valley

What’s this? I get a score screen? Something tells me the original travelers of the trail didn’t have such a luxury after their journey. 

Remember kids, you don’t need to be a doctor or a banker to succeed in life. At least, you don’t need to be one to win in Oregon Trail. No fatalities other than the ox and I get a 2x bonus at the end of it. Think you can beat my score? I’d like to see you try.

How to Play Oregon Trail

Sure it’s an iconic piece of software, but is it a fun game? It can be, depending on your expectations. It’s not what you’d call an easy game, though the game’s developers have tried to make it more accessible over the years. As much as I wanted to see some statistics about the health of my party and how much things like bad water and lack of grass affected them, such statistics wouldn’t make sense in the game world. The game requires you to think through your circumstances and how they would potentially affect your party. I guess it makes sense that people’s health will decline when they’ve had access to nothing but bad water for five days, but I’m still at a loss to explain how and why people break bones so frequently. Considering the base game was programmed in the seventies the depth of the game’s options are still a bit impressive. There are a lot of contributing factors here, and branching paths offer some interesting complexity that makes me want to try playing the game again. I do plan to play some more; partly to see if I can make it to Oregon in less than six months, and partly to see just how catastrophically wrong this trip can go.

I played Oregon Trail version 1.2 for Windows. My wife owns a physical copy of the game, so I copied the contents of the disc to my hard drive and ran the game straight from Windows Explorer. There are multiple copies of the game .exe. The location of the file varies depending on where you copy it, but within the game’s directory it was located in Oregon Trail/OTWIN32/OREGON32.EXE. As I learned the hard way, no compatibility mode is necessary. It is possible to find multiple versions of the game on sites that host abandonware (what is abandonware?), but there are some potential legal and moral implications to this. If gaming with a clear conscience is important to you, consider reading Abandoning Abandonware (Or: How Do You Like Your Piracy?).  To get around any potential issues, you could play the game for free in your browser from the Internet Archive: The Oregon Trail Deluxe 1992 Edition at The Internet Archive.

One thought on “An Evening With Oregon Trail”

  1. Yes, you MUST play it again. Anyone who skips out on rafting the Columbia, in my book, can’t say they’ve truly “made it” to Oregon. If you go through Oregon Trail feeling like the hunting is the most fun part, you can’t skip the rafting. It’s the most interactive you can get with this game; pretty much everything else is just making decisions. Hard decisions, at times, I’ll grant, but still.

    I have to add, there are a handful of versions of this game, from what I can tell, and in grade school I played a much more primitive version. This version (1.2) is the one we purchased for home play out of nostalgia back in the 90s. For context, I was probably preteen when we started playing this version and just getting into computer gaming.

    What I enjoyed about OT had nothing to do with scores. As I decided my profession and named my travelling party, this became a personal (albeit virtual) journey. I cared about my travelling party and a microscopic part of me mourned whenever one of them died along the trail and I had to face the concept that they would not be a part of my new life in Oregon. The game introduced me to songs I’d never heard but grew to love (so much so that I actually went in search of a “soundtrack” for the game, to no avail). Side note: While skimming through the ReadMe for OT the other day, I discovered a note saying that if you put the game disc into your cd player, some of the songs from the game would be playable as music tracks. I haven’t tried it yet.

    I love that this isn’t a game that you can easily predict. You have to learn it. And the best way to learn it is by replaying. Every journey to Oregon is different, and figuring out the little idiosyncrasies of the game and the situations it presents, as well as the results of your own actions, and how it all comes together is part of the mystery. You’ll learn a little about the Oregon Trail and life back in the 1800s, you’ll learn more about the perils of said Trail and how to prepare for them, but you’ll also learn how the game works in a sense. As you mentioned, stretches of bad/no water will bring down your party health. Hunting in the same general area within a few days will result in little/no game to kill. Resting when party health declines or a party member falls ill will result in faster healing and health recovery.

    Some of these things are common sense, but so many games these days are less about common sense and more about entertainment. Whenever I play, I always adjust the hunting time to go for 2 minutes. And there have been times, when I have played in the past, that I went hunting in the same spot more than once out of boredom, desperation, or just plain ignorance. You can literally go on a hunting trip in this game and NEVER see an animal if you do this. I would foolishly hold out hope that *something* would surely come bounding (toward that same river I hunted at 300 miles ago) across the screen – even if just a squirrel – and I’d come back with something for my starving party. How many games do things like that anymore? Let you sit bored for 2 solid minutes waiting for something – anything – to happen, but leave you disappointed and returning empty-handed to your wagon? (As I haven’t been gaming for a while, there may be more than I think). It just seems to me like little, unassuming Oregon Trail, while not intense and action-packed, still has something unique to bring to the gaming table. I’m excited to have the chance to play it again. 🙂

    Liked by 1 person

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