Hey man - I grew up in that area, spent my all my summers backpacking. My mom still lives up there, I'm overdue for a visit myself.
You could easily hike up Hood if you wanted, the south side slog is well within your abilities. Crampons/axe for summit. You might benefit from a local partner; I have a buddy who I might be able to drag out or you could check on CascadeClimbers. Spring is the primary season but folks climb it year-round. Gotta keep an eye on conditions.
Timberline Lodge is a cool spot, you could hike up to Illumination Rock or even ride the lifts up the Palmer. Timberline in the PNW is real low, 6000' or so.
The Timberline Trail circumnavigates the mountain. The entirety might be a little long for your purposes and a section got wiped out a couple of years ago. You could drive in through Lolo Pass, do an out-and-back across the north side, real nice up there.
http://www.portlandhikersfieldguide.org/wiki/Timberline_Trail_around_Mount_Hood_HikeLots of cool trails in the Gorge. Eagle Creek is my favorite. A few nice spots to camp along the creek if you want to spend a night up there.
http://www.portlandhikersfieldguide.org/wiki/Tunnel_Falls_HikeSt. Helens has a fancy visitor center on the north side and some trails that branch out from it. You get a feeling for the power of that sucker, pretty impressive. The standard jaunt to the rim is from the south, permits required.
http://www.fs.usda.gov/detail/mountsthelens/home/?cid=stelprdb5144806A little further north is a real gem, the Goat Rocks Wilderness.
http://www.summitpost.org/goat-rocks-wa/170956The Oregon Coast is also pretty awesome. You can camp on the beach anywhere you like a mile out of city limits; there a few nice walk-ins and plenty of drive-in campsites.
http://cms.oregon.gov/OPRD/PARKS/Pages/OCT_main.aspxhttp://www.beachconnection.net/oregon_coast/62107oregon_coast_camping.phpOff the top of my head, those would be my first recommendations. Better stop daydreaming and get back to work now.