An Insider Guide to a Weekend in Portland

Curated by Doug Gould

Hotels:

Hipster Spots: The Ace Hotel is awesome, I would hang out there when I got bored of the office. If you want to go real Portland, the Jupiter Hotel which is awesome and connected to one of my favorite bars (see below: The Doug Fir)

Normal Hotels: DeLuxe is pretty cool. Another new hotel is called The Sentinel which is right in the middle of the city and easy to get around too. It’s an easy city to get around so as long as you’re on the inside of the 405 freeway on the westside and not beyond the 28th street on the eastside you should be fine. 

Neighborhoods if you are doing Airbnb: 

Hawthorne

Division

Inner SE - This is basically anywhere up to about 20th or so from Burnside to Division. Great neighborhood with random spots throughout. 

East 28th and Burnside - Awesome area that runs to Belmont. Great restaurants and bars plus not too far from Mt. Tabor which is a beautiful park on the Eastside. 

Northwest - Older, more established part of Portland that has a very neighborhoody-feel. More dressed up than most of the city. 

Mississippi - Awesome street with a lot of bars and good food spots in NE not far from downtown. 

Getting Around:

Best way to get around Portland is to wander. It’s really European (yes that’s incredibly pretentious and annoying but that’s Portland sometimes) in that the best way to explore the city is to have an idea of some places you want to hit and try to see things in-between spots. You can walk around the city pretty easily and it’s pretty flat. MAX is a decent way to get around but sometimes it’s quicker just to walk. One thing to note is that cabs in Portland are like fantasy creatures but they just launched Uber/Lyft so you shouldn’t have a problem rolling around in those. You for sure don’t need a car to get around. 

Things to do besides eating and drinking:

Shopping:

Buy things because there’s no sales tax! Union Way across from the Ace Hotel is great shopping. Also, there's great shopping on 23rd street with boutiques and vintage stores scattered in different neighborhoods.

Powell’s: Incredible bookstore off burnside that has any book you could ever need. 

If the weather is sunny (which is possible I swear), go to the waterfront for Saturday Market or head up to the International Rose Garden.  

Jogging/Hiking:

There’s a few jogs/walks I’d recommend to see the most of the city. The easiest jog would be to go North through the Pearl District, come back down through the waterfront parkl. You can also jog west to go check out the International Rose Garden and an incredible view but that is up hill so be warned.  Regardless of the season, everything is incredibly scenic so you should just man up and run up the hill damn hill. You can also go to Forest Park if you want to uber, there’s some incredible trails there too. 

Record Shops / Music Venues: 

Mississippi Studios and Mississippi Records are two awesome spots to check out if you are in the area. Doug Fir has a venue in the basement and is an awesome place to catch shows. Wonder Ballroom (right next to Toro Bravo) is a cool, mellow spot to catch a show too. 

Where to eat: 

Coffee and Baked Things:  

Stumptown, Coava, Barista, Public Domain, Mauriceare all great spots to get hyped up

Locale is a new spot in the Mississippi District that is worth checking out if you head over there. 

Lunch/Brunch: 

Olympic Provisions is my favorite. If you hit their location in NW you usually won’t have too bad a wait. Their polenta is unreal. 

Pine State Biscouts is good if you are hungover and feeling like eating some seriously heavy food. 

Tasty and Alder is great for brunch/lunch but expect a wait if you don’t go early. Or try to sit at the bar. 

Lardo and Bunk do great sandwiches if you want something simple for lunch

Pa-Dee: Some of the best Thai in the city and usually without a wait. 

Dinner: 

Ox is my favorite. Hipster Argentinian steakhouse that is out of this world, try to go early to get a spot. 

For sushi, Hokusei and Bamboo are both awesome. Hokusei is preferred (they fly their fish in from Japan) and actually takes reservations. 

Clyde Common is really good new American/NW food if you want to go full Portland

Ava Genes and Nostrana are very good Italian

Le Pigeon is one of the best restaurants on the west coast if you want to get fancy and go french. Book this at least a few weeks in advance. 

Beast if you want to go big. It’s a fixed menu by an Iron Chef but is so,so cheap compared to what you would pay in a bigger city. About $100 a person. 

Toro Bravo is a great Spanish place over on the east side

Pok Pok is great Thai food but has become SUPER well known. There’s another place called PaaDee on 28th and Burnside that is, in my opinion, just as good with less waiting. 

St. Jack is another awesome French place in NW Portland that’s work checking out. 

Also, most  most restaurants don’t take reservations so plan on hanging out getting drinks for at least 20 min before you get seated especially for brunch and dinner. Sometimes the waits can get real serious (90 minutes or more). Then you can have at least 20 drinks before you get seated and forget about how long you are waiting. 

Where to drink: 

Bars: 

There’s a few staples here that I really like. Most of these bars aren’t in places all by themselves, they usually will have a few other spots around them that are good to check out. 

I recommend these bigger eastside hip bars for going out are Doug Fir, Rontoms, Digapony, . You can start at Doug Fir and walk all three with hitting an awesome dancing spot, Holocene, at the end! 

Cocktails you should check out Teardrop Lounge (some of the best cocktails in the US), Clyde Common has great ones, Cask is a good spot on the west side. 

Eastside there’s a new place called The Liquor Store and Circa 33 on Belmont, Produce Row in Inner SE is cool too. 

Bigger westside bars (not as hip, very very bro) are Kells Brewpub on 21st and on 2nd Street (my best friend runs it, let me know if you head there), Jackknife, Brix Tavern, Henry’s

Departure is a rooftop bar in the Nine’s hotel that is alright with good food. Not a great scene of people but the view is cool. 

Wine Bars; 

A lot of restaurants will have great wine selections but here’s a few places that are especially cool. 

Eastside I’d recommend Enso on Stark. It’s an urban winery (so local) that’s in a cool neighborhood. 

Westside I’d recommend M Bar on 21st (really small) is intimate and cool if you want to get a bottle and hang out with some locals. 

Beer: 

Kells:  Great brewery for pints and football. The Brew Pub on 21st is a great place to drink when the weather is nice. 

Hair of the Dog,Rogue, Deschutes, Burnside Brewing are a few of my favorites too. The Pearl has a lot of Breweries then a good amount of them are spread out across the Eastside. Pearl is easier if you want to hit a bunch of them at once. 

Where to eat after you drink: 

Food carts: 

There’s a lot of them, most of them are very meh, and they aren’t open late. They mainly do very niche unhealthy things that are wild and crazy. 

Nongs is good, Potato Champion, it’s really a complete crapshoot. Cartlandia is out on 82nd and is a pod with a ton of food carts but you will see them basically scattered

Late-night spots: 

Montague: The best place to go for late night drunk food. Cajun so all mac and cheese, they have alligator, it gets rowdy late night and is worth the trip.

Luc Lac: Great Vietnamese place and open late.

Robotaco: does great Mexican food all day but becomes a complete shit-show around 2 AM when the bars let out.