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This kind of shit is fun as fuck. I trespassed into a park last weekend to watch a storm roll in on the pier, the best part was security showing up at around 1 am to do a patrol. Pretty exciting. There is also a trail system near my house and there is an old landfill that has been closed for decades now that is near a trail. I go there to hang out at times, it's a fun place to explore, always new shit to find.
My best experiences were trying to find new buildings to climb at my university. Friends and I would go out late on weeknights when noone was around. We found about a half dozen that could get climbed since they were on hills or you could get boosted onto or there was a ladder that was fenced off etc. Finding new places to smoke weed used to be the driving force, now it's just fun to explore and go places I'm not supposed to.