Born here in Portland, parents born here, Grandparents (on my mother’s side) born here. Basically, they were pioneers. Anyway, I love it here, but you are getting some excellent advice on options in the Beaver State. If money is not too tight, I’d go to Bend as many have already said. Second choice, which is not getting the same play, would be Hood River on the Columbia River, and considered to be the Mecca for Wind Surfers. I think Hood RIver has a lot of what you are looking for, trails galore, easy access in to the Portland metro area, (75 min. drive) and a very nice climate. Another long term option that people are just beginning to figuire out is NE Oregon, La Grande, Baker City environs. I think ultimately these towns will get hot for their incredible setting in the BLue Mts. and miles of quiet roads to ride, trails in all the surrounding mountains. Still a few years off for this area to get “gentrified” but I guarantee you it’s coming.
That’s reallty a no-brainer----Bend, OR. The new Boulder. Killer tri scene. Big mountain alpine skiing and huge Nordic scene as well.
This is the one place my wife and I talk about moving to (don’t think it will happen though).