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This story details me jumping back into the world of The Oregon Trail over a decade after I last played. The story is told near entirely from the perspective of the characters in game, along with a few personal thoughts I have. In short, this isn’t going to be your usual feature article. Enjoy.

When do you want to leave? The question hung in the air as I considered the near limitless possibilities. I had sat here at this Missouri outpost dozens and dozens of times before (I always loved the fact that the trail started off in the state I was raised in. It’s something small, but it always connected me a bit more to this storied trail). I had learned the harsh lessons of leaving too early and discovering the land was still frozen solid, devoid of any food or animals. The demise of my party on that trip still cut raw with me.

Not right away I thought to myself. Maybe wait until the summer, I thought. Suddenly the terrifying memories of leaving in the summer, far too late in the year came flooding back to me. Everything was perfect; shockingly so. Animals littered seemingly every square inch in sight. Crops were bountiful and nobody for a second thought of going hungry. But the Oregon Trail is a long and vicious mistress and one second she’ll turn on you and make you realize that leaving in the summer means trying to finish the journey in the winter. I doubt anyone ever discovered the remains of that trip, under the mountain of snow we were buried beneath, as we tried to cross the Rockies.

Shit, I quietly muttered under my breath. I hadn’t even started yet and already the trail was outfoxing me. It felt as if every possible time to leave I had already tried and failed at. This only seemed to fuel the belief that some had that the Trail was a siren in disguise. Calling and luring people over with it’s beautiful and enchanting promises of a new start out west. Of a land of adventure, bounty, and freedom. Of having your name written in the annals of history if you were to complete it, only for you then to crash and destroy yourself on the rocks of pride, ambition, and foolish hope.

The thought flashed through my mind for just a second, before anger quickly knocked it aside. It had to be possible, I just know I can do this… I just know.

Finally, I picked a time that I thought was neither too late in the year, as it was before summer started, and also not too early, I wasn’t leaving in January or anything. I quickly gathered up the rest of my supplies and went outside.

My merry band of fellow adventurers awaited me. Named after my decade plus collection of friends: Brandon, Matt, Charles, and Josh were with me on this journey to either immortality… or yet another failure.

Part 1: Go West Young Man.

A blazing sun rose early in the morning, blanketing us in a sea of warmth. A stunning blue sky coupled with the vibrant purples of spring greeted us as we left. It was impossible not to be overtaken with a powerful sense of hope, with the belief that this journey was something special, that we were blessed right from the start. Greatness awaits, the world seemed to be saying, and I for one never need to be told twice to go chase after greatness.

2000 miles long and covering the vast extremes of geographic challenges in America, the Oregon Trail was famed for a good reason. We had the quite farms and last vestiges of civilization when we left Missouri. The great American Desert and rolling barren prairies awaited us next. Nothing seemed to live there except the Buffalo. After that the towering and mighty cliffs of the Rocky Mountains would need to be crossed. It’s peaks reaching up and disappearing into the clouds, the tops of the snow colored mountains seemed high enough to touch the heavens above. And, after all that? Well, then you just had the easy trek down the mountains and a race to the Columbia river before winter hit and your trek would be devastated by the cold and disappearance of all other life. If you somehow managed to reach the river before winter, all that kept you from Oregon City and your new home was one last ride down the fast-running and chaotic body of water that was the Columbia river. Many an adventurer had risked it all, braved the heights of the mountains, staved off hunger, fear, and disease only to lose it all at the last second on the roiling and petulant Columbia river.

I did my best to push all of those thoughts out of my head as our wagons rolled past people living on the very outskirts of society and what Americans thought of as the known world. My tiny group left it without even looking back.

The first few days passed without much commotion. Leaving as early as we did allowed us the option to take a middle of the road approach to our speed. We also carried with us a plethora of food, medicine, and other equipment. I had learned my lessons from the past failures. I had everything down to a science and did what I could to keep everyone happy and as well-fed as one can be on a cross-country journey during the old west.

Then we hit the Big Blue River. We had to cross this turbulent, tumultuous, and chaotic force of nature. Many a trip had its wheels come off at this point. Slowly and carefully we crossed the river, as we reached the middle, the deepest point, I held my breath, and everything slowed down and then… nothing. We crossed without incident and hope grew stronger within me. We could do this I thought.

Days later as I sat outside hunting, hoping to provide some meat for the group I couldn’t believe the good fortune that had befell my little band so far. It was unbelievable, everything seemed to be going perfectly for us. The Oregon Trail wasn’t fighting back in the ways I was used too. It made me happy of course, but I’d be lying if I didn’t say I was a little unnerved as well.

I came back to the camp and decided that after the successful hunt the whole group deserved more rations and a bigger meal tonight. It’s rare to find a day to celebrate, to let your guard down and enjoy yourself while on the trail and so we ate, laughed, and had ourselves a merry old time. Staying up late into the night, talking as the stars blazed overhead, the gods watching over and wishing us luck on our journey. We were a third of the way through the expedition and everything was perfect.

It was the last good day for months.

Part 2: It Never Stops.

Rain. Unyielding, miserable, and never-ending rain greeted us in the morning. Our pace was slowed by this. The soil turned to mud, getting clogged in everything. The horses were covered in it, the wheels of the wagon were coated in it. Mud and the rain made life a hell, made the journey west a grueling, tiring slog.

Matt broke his arm. Almost certainly trying to push the damn wagon out of the muck after it got stuck for the thousandth time. The trip all but ground to a halt as we waited on him. We didn’t want it to turn into anything more serious. Our hopes were not answered.

Matt had dysentery. We were so close to the next fort where I hoped Matt could get the attention he needed and where we could re-supply for the next leg of the journey. I was forced to stop just short of the fort, concerned for the very life of Matt. So we stopped and stayed pat for a day.

You could see Matt fighting for his very life. Coughing, sweating, and clinging on with everything he had left in him. He was fighting, but he was also clearly at the end of his rope. We waited there a second day too. Then a third. Finally, on the fourth day, Matt began to improve. We left immediately and made it to the fort within a day or two. We had all made it. We had survived the hell of the never ending rain and the near loss of one of our own. Re-supplied and buoyed by all of this we left the fort feeling just a little bit better, more confident that maybe just maybe we could do this crazy thing.

Then Charles got cholera.

We slowed down again and eventually were forced to stop. I was forced to spend my days hunting for food. Hoping against hope that he would improve. But I knew this story, a happy ending for everybody wasn’t in the cards.

He got weaker and weaker, slowly losing his grasp on everything else. He began to fade and there was nothing me, Brandon, Matt, or Josh could do. He was going. Frantically, I thought maybe if we traveled fast enough to get to the next fort somebody there could save him. Deep down I knew the minute we left he would only get worse, that’s exactly what happened. We had to stop again and continued to burn more time.

Charles died on a day where the rain never stopped, the weather was awful, and the scent of despair filled the air. He had just wanted to go west, to find his fortune and fame. He died broken and a husk of himself, in the middle of a field in Nebraska, hardly the ending he or the thousands of others who perished along the trail envisioned. Fortune favors the bold, but sometimes fortune is a bastard.

Part 3: Glory or Death.

The air outside was a bit colder. The days of summer were over and fall now surrounded us. We hadn’t really felt it until this morning. We had crossed the Rockies, made our way through Wyoming and now found ourselves in Idaho, towards the journey’s end, but the air was cold. A flash of fear rippled through me. Did we have enough time to make it to Oregon City? Would this be another trip that was crushed by the devil that was Winter?

We still had a couple months before winter, but so much time had been lost due to the sickness, snakebites, and death we had encountered along the way. A black cloud had hung over us for some time after Charles’ death and it was only recently that things seemed to begin to turn in our favor.

We were just a day or two away from the Blue Mountains, one of the key markers that we were nearing the end of the journey. We had come so far, spent months traveling and now, here we sat at the conclusion of our adventure. The mountains loomed on the horizon.

Soon we found ourselves trudging through the Blue Mountains and before long, without much difficulty at all, we had crossed the mountains and were at the final leg of the journey. All that kept us from our glory and getting our names etched in the history books was a short raft trip down the Columbia River.

I had never made it this far, this would quite literally be uncharted waters I was finding myself in. I had no idea what lay at the end of the rafting expedition.

So many smashed wagons and hopeful souls had been lost here, at the 11th hour of the journey, due to the swirling and traitorous waters of the Columbia. Only the Oregon Trail would have it’s final task be crossing one of the fastest and most vicious rivers in the country.

To say the ride down would be white knuckle would be about the understatement of the century. Over a dozen years of expectations, hope, and dreams were now rolled into this one frantic ride down the river. The souls of the thousands who had started out on the trail only to perish along the way due to starvation, cold, disease, or one of the other seemingly endless ways the American West sought to punish those it deemed unworthy of the promise of Oregon City now followed me.

The Oregon Trail is a video game. It’s fanciful, largely light-hearted, and without question one of the most iconic and beloved games for generations of school-children. The impact it had on games and how people view them, of history and people’s understanding of it, and ambition and it’s pratfalls and soaring successes is near incalculable. The Oregon Trail is also, however, a real, devastatingly deadly trail of the broken promises, dreams, and hopes of people seeking a better life for them and their families out west. It is a trail that symbolizes so much of the very best and worst of humanity. It is a trail steeped in one of the most fundamental and human of all emotions: hope. Hope that tomorrow can be better than today. Hope that we are special. Hope that this impossible, savage, and beyond-our-understanding of a world can maybe, just maybe, hold wondrous and amazing things in it. Hope that the cry uttered from the birth of man that impossible is nothing, is a truth and not simply a desperate wish from all of us.

I carried this with me as I looked out at the titanic, churning body of water in front of me. As I let my eyes wander to the horizon and let myself be deceived by the fact that it appeared as if the river went on forever. In this moment I let myself think, let myself hope, that one simple and powerful thought.

Why not me? Why not today?

And so I started onto the Columbia river and I sailed towards the horizon.