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Driving from Seattle to CA questions -OR., WA. routes & itinerary

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I am dropping my son off at college in Seattle in Sept. We plan to drive from the SF Bay Area up Fwy 5 and stay 2 days in Ashland and attend 3 plays. Then we will take the long drive to Seattle via the 5. We will spend a day doing some shopping for the dorm, then move him in the following day. I will be done about 3:00pm, but if I leave Seattle then, I don't want to drive more than 2 hrs and prefer not to take the 5 again. I will be stopping at a relatives on my way back for 1 night, just south of Bend, OR. From there, I may go to Ashland again, catch another play, for 1 night ....or not.

Here are my questions:
Should I stay in Seattle 1 more night after moving my son in, then make the long drive to Bend area the next morning (6-7 hrs). Or drive somewhere & spend the night within 2 hrs away? Where - interesting, pretty, scenic, cute town, etc. I am not a fan of very long drives, especially when I am driving by myself.

Is there somewhere else that I should go instead of Ashland, couple hours south of Bend, for 1 night before the long drive back to the Bay Area?
Maybe the OR coast is too far?

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