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I Played Through "Oregon Trail" Again and It Was Just as Good as I Remember It

And you can too! Here’s what my experience was like.

Jack Shepherd · 6 months ago

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I thought I’d never walk this woeful path again, and yet here I am...

The most thrilling news I’ve heard so far this year is that my old arch-nemesis, The Oregon Trail, is back and ready to do battle again, in the form of an affordable, engrossing, and utterly nefarious handheld game. Now, I have never been one to shy away from a challenge — to reject the call of adventure — but over the years I have developed a healthy and (some might argue) sensible aversion to dysentery, bandits, and fording dangerous rivers, and so it was not without trepidation that I embarked once again on the dreaded trail that took so much from me in my youth.

But what I have lost in courage since the days when I walked the deadly trail (as an alternative to studying, in the olde timey computer labs we used to have in the mid-’90s), I have gained in wisdom, and so I was confident that my superior strategic thinking and long-term planning abilities would more than make up for the hubris and bravado that I relied on to tread that treacherous path in my youth. 

I couldn’t have been more wrong.

Things started well enough. Naming your party is a hopeful act, and I proudly gave myself the name of a brave and mighty hero so the Trail would know my intentions: To conquer it.

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Fortified and inspired by the thought of this brave warrior smiling upon my endeavor, I chose to bless the remainder of my party with the same gift — so that we might all gain strength and protection from his influence.

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Before we could leave, we had a rendez-vous with an old, old friend — a guy named Matt. We were careful to listen to his sage advice about how much oxen, ammunition, food, clothing, and spare wagon parts we should buy from him, and we stocked up on supplies for our journey with a sense of trust and gratitude that would turn out to be misplaced.

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And so it was that we embarked upon the Oregon Trail once again, with hope in our hearts and a song on our lips. This would be one of the last times we felt this way.

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Things went downhill pretty fast from here!

First of all, Glorious almost immediately got cholera somehow.

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It’s unclear where she got it from, since we were only a couple of days out from Independence and still had lots of fresh goods from Matt’s store, but it’s difficult to overstate how much of a bummer this was for the party. 

And this was just the first of the calamities that awaited us. With Glorious still feeling pretty under the weather, our brand new wagon broke down and left us stranded. I was beginning to think that Matt hadn’t been completely on the level when he sold it to us.

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And while we were all licking our wounds about the wagon thing and the cholera ... this happened.

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Who steals six oxen? That’s ALMOST ALL OF OUR OXEN. How could somebody do this to us? I can’t even begin to describe how essential those oxen were to our endeavor. This was a major, major setback. 

Somehow we managed to press on with a quarter of the oxen we had started with less than a week ago, and that is how we ended up at the Kansas River.

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“Oh, a river!” I thought to myself. “We can wash our clothes, give Glorious a nice healthy bath, and fill up on water for the journey ahead. This will be a nice change in our routine.” 

I was very wrong about this.

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After some haggling with a ferry operator who claimed that he wouldn’t be able to get us across for another four days for some inscrutable reason, I decided that the best thing for us to do would be to ford the river ourselves. 

This was a mistake!

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Losing one of our two remaining oxen was a calamity almost too great to be borne, but that wasn’t even the worst of it. In my haste to get us across the river and back on the trail, I neglected to ask whether everyone in the party could swim. This was an error of judgement. Our dear friend Hero joined the ox and some pretty vital supplies in the murky depths of the Kansas.

This was, it goes without saying, extremely disheartening. 

At least our food rations would go further now? Maybe the increased supply would help Glorious feel less poorly.

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Or maybe not. 

It was at this point that the wheels really started to come off the wagon (as they say). I was so impatient to get us back on track that I did what I would be the first to describe as an inadequate job of keeping an eye on our food situation. 

Which is to say that we ran out, and I didn’t notice. This was a failure of leadership on my part, but I will say in my defense that the rest of the party was so busy trying to show how brave and self-sacrificing they could be that no one mentioned to me how bad this problem was until it was far, far too late. 

First, Binks got sick.

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Then someone took our clothes.

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Then Binks got really sick.

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Gungan wasn’t feeling so great either, though — again — if he had taken a second to mention to me that we had completely run out of food at this point, I really feel like I could have done something about this.

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A short rest did not help matters.

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Perhaps a longer rest would help to restore some of the fighting spirit that we had all started with! We could spend the time stoking our campfire, stoically pretending that we hadn’t run out of food some days ago, and singing songs to keep the mood light.

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The mood did not improve. 

I decided the best thing to do was to press on. Glorious, who was still feeling pretty unwell on account of the cholera and typhoid, had a run of what I can only describe as truly awful luck.

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It was at this point that the burden of leadership began to catch up with me. I started to feel like I had let everyone down. And then I just started to feel bad in a more general sense.

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I shot some deer and a large bear to try and stave off the inevitable.

But the combination of grief, hunger, and a strong sense that all of this was somehow a result of my own poor decision-making led me to make some more mistakes. And once the mistakes started, the whole thing kind of snowballed.

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It was at this point that I gave up the ghost. 

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I left a marker so that other travelers might avoid the same mistakes that had led me to this sorry end.

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And so it was that my journey ended. The destination itself wasn’t what was important after all — what really mattered was the friends we lost to dysentery along the way.

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All that being said, I’m certain that with a bit more preparation, a bit better strategy, and a dogged focus on my food supplies and the needs of my party, next time we will make it all the way to Oregon. I can’t bear to think that my legacy will be dying of exhaustion in Wyoming. 

This is all a way of saying that this game is just as hard, just as fun, and just as diabolical as it used to be. And this handheld version is going for just $29.99, which is significantly less than a spare wagon wheel. Do you dare to try your luck on the trail?