Portland, Oregon is one of the best food cities in the US. It has one of the highest numbers of restaurants per capita, and all that competition adds up to delicious food. I have been traveling there once or twice per year for many years now, and I am never disappointed.
In addition to the great restaurants, Portland has a unique food cart scene. Don't call them "food trucks," or they will know you are from out of town. Food carts are stationary trailers that are situated in pods of two to 25 all over town, including the suburbs. There are more than 600 of them. Eater keeps a list of "Must-Have Food Cart Dishes" and very successful carts can go on to become restaurants, or, in some cases, create a multi-cart empire.
With all of this great food to choose from, it's hard to know where to start. Here is my list, in order of preference. Note that everything on this list is worth a visit, even the ones at the bottom of the list because this is my best of Portland list.
Pok Pok is extraordinary. It is worth a trip to Portland all on its own. Get off the plane and go directly to Pok Pok. Andy Ricker is a professional chef who lived in Thailand for many years. He started selling Thai style rotisserie chicken out of a shack, which quickly had lines around the block. He opened Pok Pok and started the trend of authentic Thai food in America. He was the James Beard Best Chef Northwest in 2011 and his empire now spans multiple locations in Portland, Los Angeles and New York, where Pok Pok has a Michelin star.
Castagna is home to my favorite meal from my most recent trip to Portland (besides Pok Pok wings which are in an ethereal category all by themselves). This is a fine dining restaurant driven by creativity and beauty. This dish is shima aji, satsuma orange and ginger/satsuma gel. Castagna has a cafe and restaurant. The cafe is more casual and the restaurant is where the creative tasting menu can be found.
Salt and Straw makes some of the best ice cream anywhere. They play with savory and sweet flavors. There are multiple locations and maybe you need to try them all. Fortunately, one is coming to San Francisco soon. My favorite flavor is goat cheese ice cream with black olive brittle. Delicious!
Beast is an iconic Portland restaurant. Chef Naomi Pomeroy won Best Northwest Chef in 2014 from the James Beard Foundation, and Beast is a perfect representation of Portland. There are two large communal tables, so everyone makes new friends. The food is creative and rustic, but with modern twists. The food is a perfect balance between comfort food and fine dining. This dish is the salad course from my last visit: sumac roasted carrots, chicory, poppy seed labneh and a crisp toasted yeast and thyme "glass," carrot powder.
Expatriate is an awesome bar with great bar snacks from Naomi Pomeroy of Beast. The bartenders here are top notch, and the food is equally good. This is the type of place where you simply describe what you like to the bartender and they make you exactly what you didn't even know you wanted. The menu is eclectic and delicious. It's the bar food you wish every bar had.
Voodoo Donuts is the original off-the-wall donut shop. They are the ones who started putting Cap'n Crunch and bacon on top of donuts. Clearly they are brilliant. With outposts in Austin, Denver, Hollywood and other Oregon cities, we can all hope that one will be coming to our hometown soon.
At Cacao you can learn everything you ever wanted to know about chocolate. They carry artisan chocolate from all over the world, and the chocolate enthusiasts that staff the store can tell you everything about the origins of the cacao, the processing and the producers themselves. Buy all the chocolate you want to take home with you, but don't forget to get some thick, rich drinking chocolate before you leave.
Pollo Bravo is a Spanish tapas and chicken stand inside the new Pine Street Market. Their chicken is legendary, and their jamon and croquettes are on point. They also carry an iconic modernist dish: the spherical olive, which was invented by Ferran Adria at el Bulli in Spain. It looks like an olive, but is actually an olive gel surrounding a liquid center of olive juice.
Pine Street Market is a new food hall in Portland. There are nine restaurants inside the market with a large, communal seating area in the center. Most of the purveyors are well established Portland restaurateurs bringing their best offerings to the market. There are burgers, Korean street food, Salt and Straw soft serve, Spanish tapas, German sausages, and more.