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As what goes everywhere, try to find a place close to work.
There are shitload of parks in the area. Forest Park is the largest wilderness within city limits anywhere in the United States. My personal favorite is the near by Japanese Garden, although I wouldn't walk my dog there, there's an entrance fee.
You'll want to go to Powell's Books. Also, check out their technical book store. And Voodoo donuts. Restaurants tend to change a bit, I don't know what the latest is. The Portland Mercury is the best paper in town, and you can find lots of things to do inside.
Just outside of town- to the east is the Gorge. It'll be beautiful this fall. Take the old scenic highway where you can. To the SE passed Beaverton there are some nice areas to go for a drive, near Newberg there's a nice hill (Baldtop?) with some beautiful views of the city and country.
The best drive on the coast is the Three Capes Scenic Loop, within a days drive of Portland. The road conditions are poor, but the views are world class. Also, it's off the main highway, so there's less traffic, even in summer.
Best spot on the coast, IMO, is at the Oregon Dunes, just north of Takhenich Creek, accessed from the scenic pull out.
If I had a three day weekend, here's what I'd do: drive south to Salem, head east over the pass, stopping at various scenic pull outs, Clear Lake, the falls just below that. Spend the night, doing whatever seasonal activities are good there, ranging from skiing to river rafting. Drive south and see Crater Lake. Everybody should see Crater Lake once. West to Roseberg, getting a chance to driving through the hill country around Roseberg, it's amazing at dusk. Stay at Roseberg. Up early the next morning, and traveling west down the Umpqua, where you'll get a chance at world-class fly fishing, if you're into that sort of thing. The Umpqua empties into the Pacific at Reedsport, which is just a few minutes south of Takenich Creek. And then it's up the coast and back home to Clackamas, stopping anywhere along the coast that you'd like. You can head back east to I-5 at Florence, Newport, Lincoln City, or any number of places depending how long you'd want to drive up 101.
But there are plenty more places on the coast worth checking out. Darlingtonia Wayside, Sea Lion Caves, The Hobbit Trail, Seal Rock, and so on.
Lots of neat vineyards for wine tasting in the Willamette Valley. Oregon has the best microbrews in the world. Good spot for hiking is near Opal Creek, east of Salem. It's got some amazing Old Growth that escaped the chainsaws. Also it's got one of the best swimming holes I've ever seen.
And if you're insane about hiking, there's the Devil's Staircase. But that's for advanced Oregonians.
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