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Gravelpit.
I distinctly remember playing as engineer and having no clue what to do.
 
skial dustbowl with the old fags Flaming Taco Shits was the person who made me favorite the server so it was the only map I played for about 6 months
 
cp_steel, I kept getting lost and now that I think about it I still get lost.
 
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Skial Mountain Lab NY
R.I.P. Sweet Prince

Played it for 95% of my total connection time and met some of my longest ingame friends from there.
 
Dustbowl. Stumbled upon US-21 a few years ago. Edit: back in 2011
 
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Mine was this weird-ass surf map where I just mostly ran around the "Jail" looking for people to kill as heavy. I was like lolwut is this cause I had no idea that Team Fortress 2 had custom maps.
Turns out I joined since I just clicked on the server with the lowest latency. :(