The Oregon Trail is such a classic video game that at this point its legacy may have even gone beyond the medium which birthed it. One quick google search reveals autofill results such as 'The Oregon Trail Book' or 'The Oregon Trail Board Game'. Suffice to say the original title itself doesn't get a huge amount of play these days. I kinda doubt that youngsters even boot this game up in computer class anymore; I think these days their teachers opt for class via Minecraft instead. But anyway, the game itself has held up (imo) surprisingly well. The Oregon Trail has a pretty simple gameplay loop - you travel the trail, hoping to avoid bad rolls on things such as weather, sickness and other random factors. There is hunting, resource management, decision making and a nice amount of American history to absorb. The best versions of the game are (naturally) not the oldest - for this review, I played the newest official version of the game, The Oregon Trail Deluxe, released almost 15 years after the original. While the graphics, color and writing have all received significant upgrades, the core gameplay remains largely the same. Which is why, for all its strengths in visuals and atmosphere, the experience remains largely held back by the design choices of the original. When you're given the choice to either ford a river or caulk the wagon, and then proceed to sink, there isn't any good feeling to be had whatsoever. Both options are blind dice rolls - there's no way to say to yourself "I should/could have taken this option" because there's no way to have known what option would give you a bad outcome. Simply put, there simply isn't much strategy to be found in making a lot of these decisions. Primarily this has the effect of making the game feel harsh, random and unfair. But it does have the side-effect of realism; shit was tough in the wild west, and if you wanted to make the trip to Oregon you were in for a rough time. This might be a lame excuse, but real life is harsh, random and unfair, just like The Oregon Trail. Vague choices with harsh outcomes and randomly assigned afflictions (another one died of dysentery!) make the game less fun, but they also make the completion of the journey that much more of a difficult, coveted accomplishment. That's why I feel the difficulty, though undeniably arbitrary, is a double-edged sword. It makes the game less fun, but it makes it that much more realistic, that much more more tense, and that much more worth bragging about if you completed it in computer class.
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There should probably be a genre for "trail-like" games. There's multiple examples of games directly copying the foundation of Oregon Trail (most obvious is Organ Trail).