this post was submitted on 06 Aug 2025
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We of the fabled Oregon Trail Generation had the unique experience of an analog childhood and an adulthood in the digital hellscape we all know and love.
So when we wandered off into the woods for hours, or even once I could borrow a car and head over to a friends' place? Completely unreachable. The only exception was the house phone at a friend's place if we were there.
When I was in college, Wi-Fi was just becoming popular. The equivalent to walking down the sidewalk with your face in your phone was the couple grad student TAs who were busy or nerdy enough to walk between buildings holding their laptop open in front of them. Wi-Fi was not built in of course. It was a PCMCIA card sticking out of the side.
When we were home or in our dorms, we didn't sit on our phones, we sat on our PCs! And now decades later I've transitioned back to sitting on my PC at home and it's great, lol.
My first personal cell phone of any kind was my dad handing me down his old work phone when I finished college and moved a couple hours away. It was a Motorola Startac motherfucker! Look it up and be jealous!
It's funny because I'm only in my mid 40s and have very little gray hair. I don't feel like an old, but I have absolutely hit the point of the "back in my day" attitude. I usually don't actually say anything unless I see a good joke in it, because that would be cliched and obnoxious.
I bet there's something about being the age where you could be a grandparent. There's something pretty damn wholesome about watching people who are young enough to be your children having their own families and careers and stuff. We had our kid about a decade later than we wanted, so I think my son gets to benefit from me being half chill grandpa and not 100% frantic young parent.
Never heard the term Oregon Trail Generation before but immediately knew what it meant. That's a great name.
I agree! I only heard it in recent years which is pretty recent relatively speaking, but it instantly made complete sense.
I think the most recent memory I have of playing it in school (not emulated later or something). I did a search to look for dates, and I found this awesome short article about the creators. The origin story makes the game even better in hindsight.
https://www.smithsonianmag.com/innovation/how-you-wound-playing-em-oregon-trailem-computer-class-180959851/