If you're planning on heading north on highway 101, I highly suggest staying on it until you reach the turn off to head towards Montesano, and in towards Olympia. Cannon Beach,OR and Seaside, OR was where I spend a couple of days surfing, and the stretch of highway from Cannon Beach to just before Montesano was great. Soooo many awesome views, and if you're lucky like I was, you'll get the road mostly to yourself. At that point it literally turns into a track straight out of need for speed.
If you're planning on stopping in Portland at any time, head west out of the city on highway 26 towards Cannon Beach and then head north on 101. The highway going west to Cannon Beach was also really really incredible towards the end. Smooth pavement, high speed sweeping turns, etc. Definitely recommended. This is a photo of my car somewhere just outside Cannon Beach.
If you have the chance to stop, I would also recommend stopping at Indian Beach just outside of Cannon Beach. Definitely the coolest place i've ever surfed. The views were something straight out of a movie. This is a photo I grabbed of Indian Beach.
Another really awesome drive is Chuckanut Drive. Its just south of Bellingham, and west of highway 5. Takes an extra 5 minutes to do, but man is that road really cool.
As far as gas jockeys go, I told them to isspay off every time I had stopped for gas. Some of them understood, but most said "sorry bro, its my job"... That frustrated me a lot.
I have a ton of footage from my trip, and this is really getting me to want to look back at all of it. I may post a few stills or even some video from it in here if you want.