All Downtown and the Pearl District is great to simply explore. The gondola up to the Health Campus is a great vantage point of the city. Endless Brewpubs and street food.
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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Oh, just remembered another great find when I was there last week! Go check out the Multnomah Whisky Library and insist that you sit in the library. It's rad.
Powell's City of Books is a must see if you like reading. They have over four million new, used, rare, and out-of-print books. Its the size of a city block. You could spend a life time looking around in there.
Portland is one of the best places to visit....if you like beer. There are new breweries popping up constantly. There are also great little cafes and restaurants everywhere. My advice would be to just do some research on restaurants and breweries you want to visit and uber around.
I will echo Voodoman's comments that the food is just of excellent quality, and not overly expensive.
The other thing Portland is known for is strip clubs. They claim to have the most strip clubs per capita. It's actually kind of annoying, as the night life there is no great, and you'll just be trying to find a regular club....but it's actually a strip club. They do some pretty cool alternative style stripping. I went to "stripperoke" at the Devil's Point, which was actually pretty fun. Mixed crowd. I took my girlfriend, she had a good time.
I always have a great time every time I go to Portland. It's just a very laid back place, where you can walk around and drink and eat.
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Portland is a city where record stores are still thriving. There are lots of record stores, lot more than one would expect from a city of that size and population base.
Things to do in Portland?!?
