there's alvar aalto's mount angel abbey library

it's one of only two aalto works in north america

Well, I don't know much about architecture from that area, but I would recommend the following:
- Crater Lake, Oregon (a little over 2 hours)
- Its a long drive for a bridge, but Calatrava did a bridge in Redding, so maybe you could hit that up on the way either to or from Ashland
- Table Rock
- Pilot Rock
- There used to be a bunch of art galleries in Ashland, whether or not they are still there (or any good) is anyones guess, last I remember there were a bunch along A Street (next to the railroad tracks), and a few in between there and downtown
- Not sure if plays are going on, but you should check out the Oregon Shakespeare Festival

Food/Other
- You gotta try the Lithia Spring Water, there is a fountain of it downtown on the plaza. Be sure to take a nice big first gulp
- Get breakfast at the Breadboard, I recommend the Mt. Man
- Go to the Greensprings for a day, its a nice place, and the Greensprings Inn has great food.

Thats it for the time being, I just saw this thread and had to comment. I will try and think of some more things...

Thanks for the suggestions. The Alvar Aalto library unfortunately is too far out, but the rest I'll add to the list. Jah, sounds like you're familiar with the region. What about en route (like the Calatrava bridge, which I'll definitely check out)? I've only been as far north as San Francisco before and was already planning on hitting the Redwoods either going up or coming back down.

big fan of mt shasta and esp. castle crag rocks state park near border... I remember there being some really good restaurants in ashland, and also this one place in the tiny town near castle crag...

Yes! I can't believe I didn't mention Mt. Shasta. Its gorgeous. The Redwoods are a must see. Truly amazing.
I am not to familiar with what is between Ashland and San. Fran, so I won't be much help in that department.
Also, the Oregon Caves Monument is pretty cool. If you drive out that way, you should stop and get some sausages & "trail busters" jerky @ a place called "Taylor Sausage" in Cave Junction. Just typing it makes my mouth water... MMMMMMMMMMMmmmmmmmmmmmm...
And yes, there are a ton of good restaurants in Ashland.
Happy Falafel is good.
Giseppis Pizza is good (lunch special only)
House of Thai
The Ashland Co-op has a pretty good deli, and quite the scene to accompany it
Shop-N-Kart is the place to get cheap beer and good groceries
Chun's Palace (near Co-Op) has good chinese food
like I said before go to the Breadboard. Its really, really good.
And go to the Greensprings/Hyatt lake. Get food @ the Greensprings Inn. Hell, stay up there for a nite.

Alright, I think thats it for now, I forget about stuff and then remember, and then forget... I will try to give more info when I think of it.