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?
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South towards California
You can take the 30th Avenue and head east. You can probably hitch a ride at a bus stop, especially during rush hour. At the on-ramp there's quite a lot of traffic, but you might be better off waiting on the freeway itself (which is legal in Oregon).