Eugene is almost an anarchist stronghold in Oregon. By all reckoning, a dandy loc. Amazing library. Go to the Whiteaker district. Maybe this is where you can learn to start hopping trains?
Eugene also has a good amount of free meals if you are looking for food. Check out the Dining Room. The library is indeed amazing. Lots of great parks, too. There's a 24 hour Shari's out on West 11th for coffee camping. Near there, too, is a pedestrian underpass that I have successfully slept under. Also the woods near there can be a good spot for urban camping.
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South towards California
Exit 195A/195B is the best place to hitch south as the adjacent on-ramp has a wide shoulder, is visible to freeway motorists as well and has a well lit street which provides adequate lighting if you find yourself hitching after dark. The 30th avenue on-ramp is also good but traffic is lower and areas for camping are more sparse.
North towards Portland
You can take the number 12 bus past Gateway Mall. At the Delta Highway intersection, there is an onramp for north, but not for south. There is not much traffic on week days, but getting to Salem, Albany, or Portland seems alright.