When you're in Portland you should check out Hood River then. It's about 45 minutes east of the city, a town of about 5-10k in the Columbia River Gorge. The scenery's great - you've got the gorge & river all around you, then a broad valley with orchards & wineries heading south with Mount Hood towering above them. The town itself is a little yuppified but the side benefit of that is that you can find restaurants, shops, etc, that are pretty decent for a small town. It's one of the places we're considering.
http://en.wikipedia.org/wiki/Hood_River,_Oregon