Mt. Hood National Forest
Majestic Mt. Hood is about 50 miles outside of Portland. Gaze eastward from the city on a clear day, and you can't miss it. The surrounding wilderness offers four ski areas as well as plenty of hiking, fishing and camping opportunities. Not extreme enough for a sporting fiend like you? Then consider climbing to the peak (elev. 11,249 ft.).
Whatever your activity of choice, be sure to stop by the Timberline Lodge, a must-see not only because it's where the movie The Shining was set (and who doesn't want to run around shouting, "Redrum, redrum?"), but also because its WPA-era design marries rugged frontier chic with Native American craft and is quite natty. If you have the time and the cash, an overnight stay here is recommended.
If you're heading to the mountain during winter months, you will likely need tire chains, which probably only about 1.5% of the population know how to install correctly. Instead, use public transportation such as the eco-friendly Grease Bus, which runs on vegetable oil, or the Sea to Summit shuttle.
Willamette Valley Wine Country
In 1965, a guy named David Lett, who had a nose for finding excellent grape-growing soil, planted the first Pinot Noir vine in the Dundee Hills, 28 miles southwest of Portland in the Willamette Valley. Lett started a small but potent revolution. The Dundee Hills are now where you'll find most of the old-school wineries that made a name for Oregon with their world class Pinot Noir. The countryside makes for a beautiful drive, but if you can't find someone to be the designated chauffeur, there are plenty of touring companies that will cart you around as you swill. And you'll want to swallow this stuff instead of spit, for sure.
The old-guard wineries, which have honed their visitor operations into an art form, include Sokol Blosser, Erath and Eyrie. But there are close to 30 vineyards and wineries in the area to pick from. Note: often the vineyards and tasting rooms are in separate places.
If you're looking for lunch to balance out your alcohol intake, casual Dundee Bistro, owned by the Ponzi wine family, is a good stop featuring local flavors and ingredients.