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Also of note: Willamette Mission State Park , not to far from Champoeg, now has hiker/biker campsites. IMO a much nicer place to camp than Champoeg
If you get water and decide to go to Monument Valley I recommend you take route 261. It has a spectacular view of the Valley of the Gods. It also cuts off some mileage going to Mexican Hat. There is set of switchbacks that are dirt/gravel going down the mesa but it is a short section and you can walk if it you need to.
Get hold of the Michelin Regional Maps, they're pretty good for finding quieter roads, look for the green highlighted roads, they're scenic routes.
indyfabz & johnsondasw - Your comments lead me to believe that the ACA maps suggested by Fred would round out many of my questions relating to overnights and supplies etc. From there, figuring out when I could jump an Amtrak home should allow me to flesh out a trip itinerary.