I'm not a big tourer or anything, but I have a friend in Salem that I would like to ride my Surly Pacer to go and see. So, I assume plenty of people have done this ride before. What routes do you take?
Just did this last Saturday. 99/Barbur to Newberg, take the 219 south. Beautiful country, plenty of shoulder, not too many cars, virtually no hills. A great ride except that I've run into fairly strong headwinds every time I've gone this route.
I assume you are starting at Mt. Tabor.
You can ride south on the 205 path, now under construction and easily stay on 99E or find lesser traffic roads near there. I went to Champoeg park a couple of times from Tabor that way, on the east side of I-5 the Canby-Marquam Hwy looks pretty good, if you go west of I-5 you can take 219.