Scott T Offline Upload & Sell: Off
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I'm confused by the contradicting recommendations and I live here. 
Yes, Cannon Beach can be annoyingly crowded Memorial day to Labor day, but it's a quick 2 hours from PDX and you get iconic views from Ecola Park and of Haystack Rock. A search on 500px will give you an idea.
September is my favorite time of the year here, it's sunny and usually still warm, though as others have said, the Coast is completely unpredictable and varies day to day (even hour to hour). The Coast Range is green year round. Bend and Eastern Oregon are high desert, I think they're more brownish year round.
In the Willamette Valley, it is more temperate and they burn the grass fields at the end of summer. You will get nicer scenery in May, but it will likely be raining and cooler, summer doesn't start here until AFTER the Rose festival, mid-June. 
You have a great trip planned, you'll hit the highlights and will see a wide variety of scenery: sandy beaches, rugged coastline, farmland, desert, mountains...you'll be busy.
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