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Fall colors in Oregon - road trip itinerary advice needed

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We are planning a road trip from Portland (arriving from San Diego, CA) in mid-October with the goal of not only seeing this beautiful state (for the very first time) but also hopefully experiencing some fall colors (which I have never really seen! :P). We probably have 7 days with day 1/7 likely in Portland. My somewhat loose itinerary at this point is to go through Hood River, Mt. Hood, Bend, Crater Lake, back to Portland - I am open to changing the itinerary completely. I have been reading up other itinerary posts and see a lot of recommendations to see the coast and visit wine country. While I am sure this will not be our only trip to Oregon, should I throw in a day going to Florence/Newport/Cannon Beach/Astoria? I am from a beach town but then the Oregon coast looks considerably different in pics. Also, should I throw in a day trip to Williamette Valley for the wineries? Is the best hope of seeing fall colors in the Mt. Hood area?

Day 1 - Portland (land, explore, overnight)
Day 2 - Drive to Hood River, The Dalles, Colombia Gorge (day trip - http://byways.org/explore/byways/2141/itinerary/53147)
Stay in Hood River or drive to Bend?
Day 3 - Explore Bend, Crater Lake (stay in Bend)
Day 4 - Williamette Valley (stay in Eugene, Springfield)
Day 5 - Head out to Florence/Newport/Lincoln City (stay in Depoe Bay?)
Day 6 - Cannon Beach/Astoria? (head back to Portland)
Day 7 - Portland overnight
Day 8 - Fly out

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