October's too late, SF's too far.

Agree with bbqboy.
I like the Oregon coast better than Washington coast.
My idea would be to fly to PDX and see the Columbia Gorge and Mt. Hood before heading over to Astoria for the trip south on US 101 along the Oregon coast. You should plan on going as far south as Crescent City California and then on US 199 to see the Redwood NP. The Oregon Caves are off 199 before you get to Grants Pass. Try to get over to Crater Lake and then choose whether you want to go up the east or west side of the Cascades to get back to Portland. You could take a day trip from Portland area to go see Mt. St. Helens in Washington.

Oregon coast, Columbia River Gorge, Mt Rainier, Olympic National Park, San Juan Islands, and Seattle are a few of many places of interest in OR and WA.

Basically, I like to wander and stumble across little treasures to remember.

Will too much information thwart your favorite activity?

HTTY

I see this is your first post - welcome!

How much time do you have altogether? And where are you coming from?

In pure driving terms, SF to Portland is around 10-11 hours by the fastest route, 13 or so to Seattle. If you use the coast, which of course is much more scenic, then you need to add 4-6 additional driving hours (wheels turning.) So if you're looking at a driving trip with a return to SF (or starting in Seattle/Portland and doing a round trip to SF) with just a week you'd spend a big chunk just driving. A one-way trip would be easier but more expensive considering rental car one-way costs.

In terms of your priorities, well, there are plenty of places that will meet your requirements. Over Labor Day weekend, Seattle's Bumbershoot festival is one of the premier music events on the west coast, even the country - www.bumbershoot.org.

The Puyallup Fair will be going on in Washington in mid-September, but by October things will have quieted down on the fair/festival front. Both Seattle and Portland are arguably at their best for visitors in September and October - no crowds, usually decent weather, even some autumn color here and there in mid-late October.

Check out McMenamin's various hotels and venues in Oregon - www.mcmenamins.com, and the Highway 99 Blues club - http://highway99blues.com in Seattle for funk + music, and let us know a bit more about your time and interests. It's a great time to visit this area.

Gardyloo, I'd not heard of Bumbershoot before - and my DH has music festivals on his list of "things to travel for when we retire" - do you know, is this like JazzFest in New Orleans where you buy one ticket and then can see any number of performances, many of which are going on at the same time on different stages? Shoot, if I could, I'd come this year!

...do you know, is this like JazzFest in New Orleans where you buy one ticket and then can see any number of performances, many of which are going on at the same time on different stages?

Yes. Look at the calendar on the link I posted. Bumbershoot is all over the map in terms of music/performance types, but weighted somewhat toward current and emerging performers rather than older or more "retro" groups. But Tony Bennett is coming this year, so maybe that gives you an idea.

Yes. Ditto the Bumbershoot suggestion. It's a fantastic festival (although has gotten quite pricey in recent years, used to be free!)

Thanks for all the replies. I really, really wanted to come in September, but my friend can't get off work until October. I had thought that may be too late. I'm in Virginia. October for Maine sounds great but I just wasn't wrapping my head around it for Portland or Seattle. I'll skip SF and just focus on OR and WA. Is there a better time - in the spring - that would be good? I figure the summer is going to be too crowded.