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Going to be heading out June, bound for Portland. We'll be starting off from Ashland. Any advice, or info I should know?

Hello! I'm a writer who is in love with traveling in all its forms. I am currently easing into the vagabond lifestyle. I'm new at all this but I plan to learn as much as I can. Everyone on this site seems pretty jam, hope to talk to all of you at some point or another.