Hopefully someone else will still want the info at some point.
Powells books. Im pretty convinced that noone could dislike it. Best large bookstore on the continent, easily.
McMennamins is now classic. Theyve got some very interesting locations. I like the food at rogue better. Everyone except me seems to love lucky lab.
Getting up into washington park(the arboretum) or Mt Tabor parks are pretty cool. You get the best effect of all the green livingness of the area, while also finding great spots to look out over the city. If youve got a bicycle, the springwater trail is a nice easy, smooth ride that can get you another view on the city, meshing the neighborhoods, some nature, a touch of industrial, etc. I think if you are motivated to ride the whole thing it gives you a great visual balance that represents Portland very well. Minus some of the hillyness.
We also have the best philly cheese steaks in the country. And the numbers of food cart pods seem to increase exponentially every year. Thats a crapshoot, and whats really good seems to vary constantly, but it provides options.