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Train hoppers/crusty kids a cool in my book so long as they have cool stories.
Where I in the summer there is a decent chance of people who rode trains into town showing up at music venues and can be fun to talk to, they spend more time /out/ than a lot of avid outdoors enthusiasts I know. I would into trainhopping but on the east coast all but a few trains just go up and down the east coast instead of heading out west to anywhere cool to me. Props to people who do it though.
Though I'm always sure to stay away from the vegan preachy trainriders. And always get to a restroom before you guys wrecks it with a combo giant shit and hobo shower.