His friends implied that this was a likely quite early on, and I banged on about it myself, but it was discounted by many here as being a one off incident (the hitching home from the library in a snowstorm).
IMO if his friends suggest it was something Dylan would do (away from parents' watchful eyes), plus the fact that ER herself saw fit to give Dylan a talking to about the dangers of hitchhiking (apparently before he left for this visit) then it seems like a pretty valid possibility to me. His friends have suggested more than once that Dylan was not shy about taking risks - in the most recent clip of his friends they make reference to him having jumped off a bridge without knowing if it was safe to do so.
I've always felt that Dylan may have been impatient about waiting for his dad, scooped up all his belongings and headed out the door to start making his own way to Bayfield. It isn't unreasonable to think that he may have thought that a local who knew him would pick him up - or he may have even thought he would get a head start and catch his dad on his way back home.
:moo: