I love Portland's progressive culture, but occasionally it is cloudy and rainy for 3 months STRAIGHT. Summers are PERFECTION but winters are long and gray, and the moist air means the cold feels colder (while in Bend it's dry so doesn't feel cold even at 50 degrees--in the sun). Actually I love the moss and ferns of "the wet side" so maybe you will too but many people come to Bend form Portland, at least for a weekend getaway to find some sunshine (we have 300 days of sunshine a year; even when it thunderstorms or snows, the sun often comes out later in the day). Portland has lots of neighborhoods, a wonderful thriving downtown, good diversity, and very progressive culture (lots of vegan, gay, resale shops (like Powell's Bookstore) etc etc). Unfortunately being on the main N/S corridor there is also meth and other drug problems and the mild temperatures mean plenty of homeless. Just so you know. Portland also has a GREAT ZOO, Children's Museum, MAX (subway), and botanical gardens. <3
The countryside IS pretty close, depending on which side of town you live (getting THROUGH town is the difficulty). The Oregon Coast (note Oregonians do NOT call it the "beach" because it's usually cold and windy) is close, and the Columbia River Gorge offers great and very close getaways. Oregon has many hot springs, waterfalls, and hikes. (See Breitenbush Hot Springs resort). Go to REI to look at guidebooks; Scott Cook is one good author; William Sullivan is excellent also. The Wilamette Valley, south, has lots of orchards (Harry & David started down by Ashland). Check out Ashland, also---smaller town feel but still progressive. But VERY "white" while P-town (Portland) has more ethnic diversity--Asian, African American, Latino, mostly.