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yoshy
My limited knowledge of Oregon cycling is the portion of my Pacific Coast tour that went from Tillamook on the coast, West of Portland, down to the border with California. (See photos on page 1 here, starting from the first bike/coast pic down to the "Welcome to California" sign!)
We put bikes on the bus from Portland to Tillamook, pretty cheap and convenient. Maybe we were lucky with the weather but besides a very predictable mist in the morning, it was generally pleasantly warm and dry, with a reliable tail wind all the way. (Everyone does the coastal route North to South due to prevailing winds.) Hwy 101 is a very pleasant bike ride, and hiker/biker campsites make for very convenient touring.