Bend is awesome, basically my home away from home. Mountains, rivers, beer, etc. Hood River is great, Corvallis is decent but has some awesome breweries, Eugene is a big hippie college town, Tillamook smells like cow farts but has cheese and de Garde. The entire Oregon coast is gorgeous and Astoria is cool. Baker City is in the middle of nowhere but has a nice vibe and another amazing brewery (Barley Browns).
The further you get away from colleges and dense population areas the more conservative it gets, just like Washington. Eastern Oregon has more in common with Idaho.