beach sounds good. not sure where.
Most of the Oregon coast is cold, all the time. It might be better at the southern part of the Oregon coast.
I have heard that Ashland is a good place for hitching to, but it is difficult to get out of. I'm not so sure about Grant's pass, because there really isn't anywhere to go that I can thing of.
Salem might be a good place if we want the press. Just go to the front of the capital or Water Front Park. For camping, I have family who own about an acre of woods, just south of Salem. And my other side of the family owns huge ass forest next to a farm just east of Salem. Maybe a few people can crash at my place (it might be weird for me to come home after a few months away, and be like "Sup Mom? I brought some strangers home to chill").
Redmond (close to Bend) might be another option. I have an uncle out there, who has a farm (or it was his girlfriends).
I have family through out Oregon, many frown upon my lifestyle, but they might let us stay at there places.