Mt Hood is one of the few skiing options close to Portland. In the two winters I lived in Portland the main decision was which aspect of Mt. Hood do we want to ski- more often than not I chose the drive further north to Seattle for the weekend. The mountain typical goes from fairly dense forest to alpine canyons quickly. Though the spring/ summer ski lines are Mt. Hood are really fun, but often require crevasse navigation.
Newton Canyon - Enjoyable winter tour, which primarily skis an open slope in a canyon but does have some options lower on the canyon in the trees. Lines in the trees are pretty short.
South Side - Mt. Hood is one of the most frequently climbed volcanos. For the standard route you leave timberline and follow alongside the ski lifts and sno cats to the top of palmer where you then venture to hogsback and summit. descend a similar path.
East Side - Wy' East and Newton Glacier Headwall are the imposing slopes high above Mt Hood Meadows. In the spring they often shed their vail and avlanche runs well into Newtown Canyon within the resort boundaries. These skis start from essential the same place but the headwall is 5-10 degrees steeper than the Wy'East face. You can start and finish at either Timberline or Mt Hood Meadows and either ascend the Wy'east face or traverse from the summit. if coming from the summit the downclimbing traverse involves descending steep exposed snow and exposed volcanic choss. Because of the east-aspect hit early in the day
Cooper Spur. - Cooper ski is a fantastic line that leaves directly from the summit. The east-aspect also requires an early ski. I think we dropped in about 8am and it was still fairly ripe when I skied this. The drop in has some serious pucker factor, so make sure you know the snow conditions as the top 500' or so is a no fall zone. It does cut into a chute and becomes less exposed, but then requires some crevase navigation below