We are thinking of relocating to Oregon in the next 2-3 years. Want to be within shouting distance

very, very hip and very, very liberal. If you want a smaller town, consider Hood River. It's has lots of micro breweries and sail boarders. Plus it's close to Mount Hood for those that like to ski. A little more conservative than Portland or Eugene but pretty hip over all.

The old timers are fairly conservative but the 20's, 30's and 40's are liberal and I'd say they are the majority.

If you like skiing, biking, hiking, kayaking you'll be in paradise out here. The weather is also fairly dry and sunny on this side of the mountains if you don't like rain all winter.

That would be important.

Do you want high desert? (Bend, etc.)

Or fertile temperate watersheds? (Willamette Valley, Pacific coast)

What do you like to do for leisure? Culture?

I've been meaning to travel there to visit some old friends there too. Haven't gotten around to it just yet. It's harder in the winter time with the pathways in going through mountains and likely through snow.

driving.

probably the most liberal spot east of the Cascades, anyway. Still, there are plenty of Republicans, right-wingers, gun enthusiasts, etc..

You're more likely to find a liberal mellow community if you stay west of the mountains.