Colorado (1990, DOS) drops you into the buckskin boots of a rugged frontiersman navigating the Wild West with guns, canoes, and questionable hygiene. Equal parts action and exploration, it feels like someone mashed together Oregon Trail and an old spaghetti western, then sprinkled in a few pirates for good measure. Is it historically accurate? Not really. Is it fun? Absolutely—if you like dying of snake bites in pixelated rivers.
I never managed to get past the first screen either! I must've tried playing this over 20 years ago, and even though I've never seen any mention of it until today, I can still remember that incredible frustration of getting in the canoo, and then having no idea what to do. 20 years later I learn it's actually possible to just walk to the next screen, or paddle that canoo down the stream... Who knew.
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