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I've ridden trains before, mostly from the West Coast to Chicago. It's fun and a beautiful way to travel, especially on the high line route going through the mountains and along the Columbia River. Make sure you learn the different types of cars so you don't jump into a car on a moving train, just to find it has no bottom. The first time you go, it's recommended to do so with someone who has done it before.
Also, find a copy of the Crew Change Guide. This is a long zine (a couple hundred pages) that has been passed around from crusty to hobo for decades now (the oldest I've seen was from the mid 80's). The guide lists details about train yards in all major and minor cities and transport hubs in the USA, including the markings on the trains passing through (so you know which train is going where), information on the bulls in the yard, details on the surrounding town, local laws, etc.. Find one by asking other travelers or punks and crusties. The Crew Change Guide has long since been honored by not posting it online anywhere, so if you find a copy, please do not share it on the net.
To all the haters, seriously, stop posting in gear threads for awhile and go live a bit. When did 4chan become so anti-fun? Anything and everything enjoyable posted here is written off as trash. Is the only thing that brings Anon joy anymore shit talking and hate? Very sad. How far we've fallen since the days of chiptunes and shoe on head.