I Finally Fulfilled My Childhood Dream of Beating the Oregon Trail

You can now stream Oregon Trail for free.
Publish date:
January 26, 2015
moving, computer games, Oregon Trail, XoGEEK

Have I mentioned I moved from Florida to Oregon? Probably. I talk about myself a lot on here. If you read my little synopsis of the whole thing, you know that it was a pretty enjoyable trip. No one broke any legs. No one got cholera. No one died because I decided to forge the river instead of caulking my wagon or paying five bucks for a ferry.

In short, my move from Florida to Oregon was much easier than beating Oregon Trail.

As a child, I attended a kind of hippy-dippy school with lots of “computer time.” This meant I got to play — but never beat — Oregon Trail and this weird Treasure Troll game. As an overly-sensitive child — weeping over death of my Tamagotchi and all that nonsense — who was in the habit of naming her wagon party after her family, wagon-party deaths were pretty traumatizing. After a session of Oregon Trailing, I would hug my little sister tight, whispering things like "I'm so sorry I didn't increase the rations."

I was also a nervous, jumpy kid who stressed out every time she had to “hunt.” I have no aptitude for computer games of any kind, and fairly bizarre hand-eye coordination, so shooting pixelated buffalo with my spacebar is actually my idea of hell.

Anyway, my dream of the 90s was to beat this stupid game. You may have heard you can now stream Oregon Trail for free, giving me — and anyone else who is haunted by broken wagon wheels and their failed attempts at bison-fueled cross-country trips — a chance at redemption.

My first attempt was a repeat of my childhood follies. I named the party after people/animals that I loved, and then slammed my laptop shut in a guilty rage when Angie died in a river because I once again decided to try and walk across like some kind of road-tripping, pioneer Jesus.

The second time I sat down to conquer the trail, Sean contracted dysentery. I don’t even know why. The rations were “meager” but not “bare bones.” I even let him rest for four days and he repaid me by dying.


On my third attempt, I shifted gears and used the names of dudes I probably wouldn't like: Chad, Biff, Hugo, and Clarence. (I know “Clarence” sounds kinda like “Claire,” but let’s not over-analyze this.) This was a most excellent strategy, as I cannot bring myself to give a damn about some dude named “Biff” breaking his stupid arm. He probably broke it arm wrestling in a saloon, and I frankly have no time for his nonsense.

I decided to be a carpenter, figuring I could fix wagon wheels as needed, and stocked up with the recommended amount of supplies. The store keeper had a recommended amount for everything except ammo, and I bought way too much ammo.

I set my departure date for May, as setting out too early will burn you up and setting out too late will guarantee your entire party freezes. Almost immediately, Biff breaks his leg. Shortly after, Clarence comes down with typhoid. I rest for five days but no one ever recovers. I specifically remember the game giving me little "Your sister doesn't have typhoid anymore" messages back in the old days, but I could have dreamt them as a subconscious attempt to assuage my guilty conscience.

We eventually reach our first river and I try to keep cool and use my head. The river is 2.2 feet deep and I remember reading somewhere that 2.5 feet is the cut off for fording so I decide to ford it.

This the first successful forded river crossing in The History of Claire. Emboldened by river fording success, I increase the pace. Shortly after, we get lost and lose a day. Let's be honest, it was most likely Biff's fault. We get going again and the game pauses to ask me if I want to look at a grave.

Of course I want to look at a grave, but I'm not sure what Voland was getting at.

We eventually make it to some fort or another and I decide to chat with my fellow travelers. This is a bad decision, because these people are giving me conflicting information. The first person I speak to is a little girl who tries to speed shame me. I think Biff put her up to this.

I tell her to tell Biff that if he has a problem with the way I'm conducting this expedition, he can come talk to me himself. The little girl doesn't reply because she's not real, but my husband wants to know who Biff is.

I'm starting to really consider slowing down because while Biff is certainly obnoxious, I don't want him to die (you get more points if people stay alive), when this "Mountain Man" dude starts telling me to hurry up unless I want to freeze to death.

In the end, I decide to neither speed up nor slow down, and continue at my middling pace.

We plod along, crossing rivers and talking to randos, doing some light hunting as needed to keep the food supply above 500 pounds. I am only slightly better at this point and shoot nonsense than I was as a child, and I only go for the buffalo and bears.

If you think about it, this way of hunting makes the most sense anyway. The bigger and slower the animal, the more likely you are to hit it AND you get the most meat for your bullet this way. Because the four dudes I brought with me refuse to help me carry my spoils, I am limited to 100 pounds of meat each trip. Therefore, it doesn't even make sense to kill more than one animal; I'd have to leave it there to rot.

We trod onward, and an axle breaks. Remember how I thought being a carpenter would help me fix axles and other wagon parts?

This was false.

Like, where did I go to carpentry school? Did I only study "axle theory" and skip the lab? Are axles actually that complicated? Am I putting more thought into this than the game developers did?

After this setback, I decide to just blast through this thing as fast as I can. I also decide I don't need to talk to other travelers as much after this some clown named "Miles" mansplains the concept of shortcuts to me.

Then this dude calls me "mister" and tells me to "leave my wagon" which isn't even an option in the game. After this mindfuck, I quit talking to people entirely.

After that, it's all a blur of cholera, death, and broken wagon parts. Biff finally dies and I feel bad for feeling a little relieved that I won't have to pretend to be friends with him in Oregon. I'm really not good at ending friendships, and his death handles that whole awkward situation for me, nice and neat.

Chad and Clarence die after, and all I'm left with is Hugo. To be honest, Hugo had been so drama-free (unusual for Hugos in my experience) that I had completely forgotten about him.

Hugo and I make it to Oregon, and it's almost anticlimactic. (I hadn't realized we were that close.) We agree to "keep in touch" and but both understand that we're just being polite.

I had kind of forgotten about points.

With my points doubled, I feel slightly better about all of the broken wagon parts. But I still want to know what kind of carpenter "training" I received.

I don't feel quite as accomplished as I had hoped, but I think I found the secret to not stressing while traveling The Trail and that is this:

Name everyone Biff. No one cares when Biff dies.