If he goes to Cannon Beach he might as well go to Astoria, it is a cool town and the Coast Guard museum, which also has a history of tatooing in it, is interesting. Good history on how dangerous the area where the Columbia meets the Pacific.
Dundee, which is roughly 40 minutes south of Portland has some good wineries. The deck at Torii Mor is very nice and Lange and Sokol Blosser have some very good wines.
Full Sail at the Gorge has good views, beer was kinda average IMO. If you like coffee Stumptown has some great coffee, the cold brewed is excellent, it is right down from Voodoo Donuts.
I am going to Portland with a friend who is an UT alum and going to Autzen for the game 9/14, will not be pretty. If I didn't enjoy visiting OR I would have said thx, but no thx. Going to summit Mount St Helens on 9/12, hopefully I don't have to carry his arse up to the top.