I'm originally from PDX and head back every year. For great pub food and beer make sure you check out one of the many McMenamins http://www.mcmenamins.com/ in the area. I highly recommend the Kennedy School, the Mission Theater, or Bagdad Theater for some great food, beer and cheap movies. Cold Creek Distillery is a great tour and it serves tons of samplings. Call ahead for reservations. Deschutes Brewing Company is opening up a brew pub in PDX and this is a must see as they serve some of my favorite beer. Also, you should think about heading down to Yahmill County for some wine tasting for some great Pinot Noirs. Food-wise, you cannot go wrong with Le Pigeon, Olea, Ole-Ole (cheap, good mexi-food), Oba, Ken's Artisan Pizza (SE), Jake's Grill...so many others mentioned above in other posts
