My wife worked in PDX for a couple of years, and we generally spend a week or so down there each spring. All the stuff in the thread Troutman mentioned are great recommendations, but here are a few of our can't misses.
Pok Pok - Mentioned in the thread, but just a can't miss. There will be a line, but you just put your name on it, and head across the street to Whiskey Soda, and they will phone when your table is ready. Some menu items from Pok Pok are available there (including the famous fish sauce wings), so nice way to get dinner started.
Screen Door - Southern cooking in a cozy atmosphere. Wait for the patio, even if it is a bit cool, as they have heaters, and it is much quieter than in the restaurant. The fried chicken may be one of the best single dishes in PDX.
Powell's Books/Shopping in the Pearl - No sales tax in OR, and Powell's is the best bookstore in the world, bar none.
Apex - If it's a nice day, head up to Apex on Division. Over 60 craft beer taps, and some really interesting stuff. Outdoor seating and cash only. You can start there, and walk up to Pok Pok after, which would take about 30-40 minutes.
Hotel Deluxe - Driftwood Room (Cocktails) - A classic, dark lounge with amazing cocktails and food. They have a dynamite happy hour from 2-6 daily, with some great deals on food and drink. We sat right next to Commander Riker in there a few years ago!
The Deluxe also has Gracie's, which is a nice higher end brunch. Benedict sauce is world-class. There are a million great breakfast places in PDX, just try to be a bit of an early riser, and you'll get in no problem. The local population of hipsters don't tend to get moving before 11.
Honestly, I haven't found many/any bad places in Portland, as they simply don't survive. In fact, we just got back from Vegas, and we both said we wished we had gone to Portland instead. Would have spent half as much, and had a better time.
Also, lots of running paths along the riverfront. Great city for biking too; you can rent a bike from a few places in Chinatown or the Pearl, and ride around all day. In general, the city is very pedestrian and bike friendly. We never rent a car, just ride the LRT into downtown (we usually stay at Deluxe), and then use our feet, the transit system and Car2Go (your account works there) to get around.
Dammit, now I want to go back to PDX.
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