The Oregon Trail | Ep. 5 – Nothing Brings a Wagon Party Together Like a Little Dysentery

The wagon rolls onward, although possibly with slightly fewer healthy passengers than we would like. Tonight brought dangerous terrain, difficult choices, dwindling supplies, unexpected disasters and the traditional Oregon Trail approach to healthcare.

I hope everybody had their toilet rolls in the fridge, because this quickly became Dysentery Simulator. I had genuinely expected us to last about twenty minutes before everybody died and we moved over to Marbles on Stream. Somehow, nearly two hours later, Gary and Samwise were still alive and we had made considerably more progress than I thought possible.

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🤠 About the Game

The Oregon Trail from Gameloft brings the classic journey west back with a mix of pixel-art characters, 3D environments and modern lighting. You choose your travelling party, stock the wagon and attempt to reach Oregon while dealing with whatever the trail decides to throw at you.

That can include blizzards, starvation, broken limbs, snakebites, exhaustion and, of course, dysentery. Random events and your decisions affect both the party and later events, so a small mistake can quite easily become a much larger problem several miles down the road.

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🧭 Where We Are in the Journey

This episode continued our second playthrough from Fort Kearny, still on the first leg of five and already in terrible condition. RoyalTea, Gary, Samwise and One Mile the preacher were exhausted, filthy and enjoying the special type of love that only dysentery can provide.

We had also lost most of the useful supplies during the previous stream: ammunition, bait, medical supplies and clean clothes were all gone. We did briefly have food, but I had accidentally traded that away as well. Given all of that, surviving long enough to reach leg three was not something I expected to be writing about.

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☠️ What Happens in This Episode

We pressed on from Fort Kearny starving, stinking and generally looking like a group of people who should probably have stayed at Fort Kearny. A physician on the road at least managed to patch up Samwise and Gary slightly. Gary got some of the medicine because he was the only member of the party who was any good with a gun, although that particular skill was slightly less useful given that we had managed to lose all of our ammunition.

Things did not improve much once we started moving. A heavy rock took out one of the wagon wheels and brought the entire journey to a stop, forcing Samwise to head off in search of help while everybody else waited around becoming progressively more ill. Gary managed to catch dysentery from One Mile, RoyalTea caught it from Gary, and by the time Samwise returned with the replacement part the wagon might have been fixed, but almost everybody inside it was exhausted, starving, diseased or some combination of all three.

Then came our first loss of the evening, which was also the first genuinely good thing to happen to us. One Mile the preacher, after being allowed to read his Bible, got into an argument with Samwise, spat his dummy out and stormed away from the party. Samwise actually gained morale for getting rid of him, which I think tells you everything you need to know about how popular One Mile had become. Chat was equally delighted to see the back of him, and nobody was volunteering to chase him down the trail.

With One Mile gone, we finally managed to sort out some food. Fishing gave us a decent haul, along with a boot that was becoming worryingly close to looking like a valid meal, and we also sacrificed one of our oxen. For the rest of the evening we were no longer quite so worried about starving, although the methods used to keep the wagon stocked with meat became increasingly questionable as the journey continued.

Unfortunately, the trail soon took somebody we actually wanted to keep. RoyalTea died saving Samwise, leaving Gary and Samwise as the remaining members of the original party. We gave RoyalTea the only memorial that felt appropriate for this particular journey: “With Love, we remember RoyalTea. She is not gone, but merely walking among bacon.” It was a sad moment, but this was still The Oregon Trail, so there was not much time to stand around the grave before something else started going wrong.

Gary and Samwise pushed on in absolutely shocking condition. Both were exhausted, hygiene remained somewhere below rock bottom and dysentery was still making itself at home. We met a stranded family whose wagon needed repairing, but Gary was unable to fix it and we simply did not have enough supplies to rescue everybody we encountered. That slowly became one of the lessons of this run: apparently the best way to survive the Oregon Trail is to avoid being helpful wherever possible.

Gary’s health continued to deteriorate, which led us to search for Devil’s Club as a possible treatment. Naturally, most of the discussion became less about its medicinal properties and more about whether Samwise could simply use it to club Gary over the head. We gathered whatever berries and mushrooms looked vaguely survivable, travelled through heavy rain and generally kept moving because stopping did not seem to make anything better.

Then we came across a wounded man beside his broken wagon and three oxen. We were desperate for food, and the game gave us the option to slaughter an ox. I assumed that meant one ox. It did not. Gary proceeded to slaughter all three while their owner watched from the side of the trail, filling our wagon with hundreds of meat. The poor man eventually died beside the road, and despite checking, the game would unfortunately not let us peel him and add him to the supplies as well.

That particular decision was apparently enough for Samwise, because she abandoned the party shortly afterwards. Suddenly the entire expedition rested on Gary: injured, exhausted, recently diseased Gary. After spending most of the stream blaming him for everything, we now had to rely on him to keep the whole playthrough alive.

Somehow, he managed it. Gary carried on alone, ignored another desperate traveller asking for food, dealt with one of the oxen developing a cracked hoof and eventually reached the next settlement. Even more surprisingly, Samwise was there waiting for us and asked to rejoin the party. We accepted immediately. She might have abandoned Gary in the wilderness, but most importantly, she was not One Mile.

The settlement gave us a badly needed chance to recover. We repaired the wagon, bought medicine, treated Samwise, traded supplies and even picked up another ox. Against all expectations, we had survived the first leg of the journey and were heading back onto the trail in much better shape.

That lasted for approximately five minutes.

Gary tried using a sapling to improve the wagon and accomplished absolutely nothing. Not long afterwards his foot was crushed underneath a wagon wheel, eventually leaving him with a broken leg. Samwise could not work out how to treat it properly, so our medical advice became the traditional approach of telling Gary to walk it off. He did, limping along while we gathered more berries, avoided the poisonous ones and continued discovering that the safest possible interaction with strangers was often to keep moving.

We made it through Chimney Rock and continued towards Independence Rock with Gary repeatedly breaking himself and Samwise continuing to spread the joys of dysentery across the frontier. Somewhere along the way we also encountered Samuel and completed one of his side quests, before later meeting a Pony Express delivery man and agreeing to carry his parcel to another camp farther down the trail.

One Mile then appeared again and asked to rejoin us. Thankfully the game provided a decline button. I do not think I have ever pressed anything in The Oregon Trail with quite that much confidence.

Our supplies remained an ongoing problem. The wagon broke again, food spoiled, ammunition remained almost nonexistent and both Gary and Samwise kept finding new ways to become ill. At Independence Rock, despite everything we had learned, we even traded a substantial amount of meat for another harmonica. By this point the wagon contained two harmonicas which, according to established stream science, were thoroughly soaked in dysentery. Apparently we were no longer trying to avoid the disease; we were collecting instruments capable of distributing it.

The Pony Express parcel was eventually delivered successfully, giving us a little extra money, and we encountered another healer who treated some of the party’s injuries. Samwise appeared to lose health almost immediately afterwards, leading to the entirely reasonable conclusion that we wanted a receipt.

Chat, meanwhile, had spent the evening turning Gary’s suffering into a community project. #blameGary was already well established, but as the injuries piled up it effectively developed into the Slap Gary Foundation. Mr V was accused of throwing rocks in front of the wagon, Metro arrived ready to join in with a plank, Smith produced a backup bat with studs and there was even discussion of donating a sledgehammer to the cause. Gary’s repeated responses of “Rude” did absolutely nothing to discourage anybody.

Even after all of that, the journey refused to end. Near the final stretch of the stream the wagon became bogged down and had to be completely unpacked, shifted free and repacked. We were short on food again, had no bullets and could not afford the toolboxes we wanted for the increasingly questionable wagon, yet Gary and Samwise were somehow still standing.

Eventually we reached Parting of the Ways, where I discovered that we had made it halfway through leg three of five. That was considerably farther than I had expected when the stream started. My original plan had been to play The Oregon Trail for roughly twenty minutes, wait for everybody to die and then spend the rest of the evening playing Marbles on Stream. Two hours later, Gary and Samwise were still alive, RoyalTea was walking among bacon, One Mile was safely somewhere else and the wagon was somehow still moving.

Parting of the Ways felt like the perfect place to stop before the game remembered what it was supposed to be doing to us. What I thought would be the second and final stream of this playthrough has now become a three-part journey, because against every reasonable expectation we still have survivors, still have a wagon and apparently still have quite a lot of dysentery left to spread.

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🎥 Watch the Episode

You can see the entire sequence of poor decisions, broken limbs and unexpected survival in The Oregon Trail Episode 5 on YouTube.

You can also follow the full journey through The Oregon Trail playlist and find more videos over on Dr Ravenholm on YouTube.

If you enjoy the episode, leave a like, let me know in the comments which decision you think caused the most damage, and subscribe so you do not miss whatever happens to Gary next.

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🔴 Join the Adventure Live

The wagon is still moving, which means this second playthrough has unexpectedly earned itself a third stream. Gary still has bones available to break, Samwise still has plenty of dysentery to distribute, and somewhere in the wagon are two harmonicas that probably need destroying.

Come and join us live on Twitch or YouTube. At the end of this stream we raided into kingironblood, and those live community moments are always part of the fun.

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🏕️ Community & Links

If you want to travel beyond the stream, there are plenty of places to keep up with what I am doing, join the community and find everything else connected to the channel.

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Music — For those moments when two dysentery-soaked harmonicas are not enough:
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🌄 Somehow, We Are Still Alive

Parting of the Ways seemed like the right place to stop, both because of the name and because I was reluctant to give the game another opportunity to finish us off. Gary and Samwise are still standing, we are halfway through leg three, and what I thought would be a two-stream playthrough now needs a third.

So keep an eye out for the next Oregon Trail stream. I cannot promise better decisions, but apparently we do not need them to survive.

— Dr Ravenholm