I haven’t been back to Portland in almost 5 years so take this with a grain of salt 
And a lot of places I liked have closed.
Stay:
Downtown was fine for me. I’ve also stayed in East Portland in the Lloyd District near the convention center and it was pretty easy to get around from there as well.
Some restaurants I enjoyed:
Le Pigeon - French-inspired restaurant that doesn’t take itself too seriously
Kachka - Russian restaurant with some good pelmeni, “herring under a fur coat,” and caviar, and a large vodka selection
Coquine - a cafe during the day (with a great chocolate chip cookie) and a great restaurant at night, though I see they are currently doing a series of guest chef takeovers this summer
Davenport - fine dining-ish, I really liked their cheese and spinach dumplings
Ox - Argentine steakhouse with a great clam chowder with bone marrow
Lardo - meaty sandwiches that you can get with a side of fried pig ears
Blue Star Donuts - really good donuts. There is also Voodoo Donut which I thought outside of their novelty donuts weren’t that special, but definitely more touristy if you’re into that.
Salt & Straw - really good ice cream
Olympia Provisions - sandwiches and also sausages and charcuterie for taking home
Hat Yai - very good Thai style fried chicken
Pine State Biscuits - for a hearty breakfast sandwich to help ease a hangover after drinking too much beer the day before
I’m not up to date on Portland food carts since I think there have been a lot of changes in the last few years but it is a unique part of Portland’s food scene. I liked Nong’s Khao Man Gai but they no longer have a food cart and have moved to brick and mortar restaurants.
Drinks:
Portland is one of the great beer cities of the U.S. Some breweries I liked are:
Cascade, which specializes in sours
Ex Novo
Upright Brewing
Great Notion - actually haven’t been to their taproom in Portland yet, but I really like their beers.
Found a beer map: https://www.poweredbytofu.com/portland-breweries-list-map/
and for cocktails:
Hale Pele - cool tiki bar
Teardrop Lounge
Things to do:
Powell’s City of Books definitely check this huge bookstore out if you are a book lover
The Portland Japanese Garden was nice and peaceful. Also it is very close to the
International Rose Test Garden - did you know Portland is called the City of Roses?
Pittock Mansion - like a much smaller Hearst Castle if you’re into rich newspaper barons’ houses
OMSI - a fun science museum.
Other notes:
I thought the MAX tram system was pretty good for getting around the city without a car, especially getting around both sides of the river and also to and from the PDX airport.
Some old trip reports:
