Two more things:
Portland - I noticed the city itself isn't on your list. Powell's Bookstore is a huge local landmark and well-known tourist attraction in the Pacific Northwest. The RingSide Steakhouse is pricey but amazing. Papa Haydn (there's one downtown and one near town) serves the best dessert you'll ever have. Portland also has a huge, long-running and well-attended Saturday market down by the waterfront. Don't be scared by whatever you see in headlines, the "tourist" areas of Portland are all remarkably normal (and honestly a bit dull) compared to other cities. I've spent most of my life here and have never hesitated (or regretted) hanging out downtown with friends and family. Definitely wouldn't recommend hanging out near the train station though.
Mt. Hood - If you're going over Mt. Hood then you'll drive right by the Mt. Hood Brewing Company on Highway 26 in Government Camp. They have a small menu but really good food and their beers (brewed in house) are amazing. Definitely my favorite overall lineup of brews.
Also, definitely drive up to the Timberline Lodge, which is just six miles off the highway from Government Camp. Ignore the newer day lodge (for skiing) and focus on the historic old lodge. You will recognize it immediately if you've ever seen The Shining.

(Only the lodge's exterior was used in the film... the interior shots of The Overlook Hotel are someplace else.) At the very least you can enjoy some fantastic views of the mountain, and the old lodge also has a bar and a nice (but somewhat overpriced) restaurant.