Having grown up in pre-"Portlandia" Portland, I remember an uncomplicated (if a bit uncultured) era when the best restaurant in town was a basic surf-and-turf joint on the top of a hill, no one had ever heard of a paleta, and our annual tourist count capped out at around 2500. MY, how the times have changed! Every few days someone hits me up asking for recommendations of where to go sightseeing, what to eat, where to drink, etc. etc. etc. I love playing host to tourists and will be happy to show you around if I am free when you come to visit. On the off chance that I am not personally available, here is my list of absolute must-do's.
The best way to approach Portland is by neighborhood. The city is divided into four sections: NW, NE, SE, and SW. The river runs North to South and splits the city nicely in half. A major street named Burnside runs East to West, and everything above that street is considered to be the Northern part of Portland, while everything below it (including all of downtown) is South Portland.
SW represents Old Portland -- the Portland I grew up in -- while NW is a relatively new development with lots of shops, restaurants, and walkable sights. What you're really coming to Portland for though, the things you've read about and seen on Instagram, are probably on the other side of the river. Most things on the inner Eastside are new, hip, and ultra-gentrified. Luckily, we still have some older establishments and family-owned restaurants that have held out.
In the recommendations below, I've denoted women-owned establishments with an asterisk (*). Organizationally, I normally split my guides by coffee, breakfast, lunch, cocktails, and dinner, but for this post, since neighborhoods are so important and I don't want you to waste any precious vacation time, I'm going to split things up by district.
If you only have a long weekend, spend one day each conquering NW, NE, and SE.
To truly live the Portland lifestyle, you can't just GO somewhere, you gotta LIVE it. I've tried to include my recommendations for living it. Have fun!
Start your trip in Northwest Portland so you can knock off the major sightseeing destinations like Powell's City of Books.
If you're in a hurry, you can do Powell's in an hour, but if you're a booklover, you may need five or six hours. I was born and raised here and can still kill a handful of hours browsing books, reading the thoughtful recommendations, searching the libraries, and browsing the cute local gifts at Powell's Books any time I'm in the area. Powell's is a must-do when in town.
Cocktails and Dessert:
Northeast Portland is THE Portland you've read about. Everything you want to see, do, eat, and drink, can be done in this incredibly fun, innovative, well-designed, exciting district.
Lots of people are going to tell you to get a big crazy Southern breakfast at Screen Door. I'm not a fan. Have you ever been to the South? If so, you've already had a better big crazy Southern breakfast than the one at Screen Door. Skip the 3-hour wait and make the most of your vacation by going to one of these places instead:
Cocktails and Dessert:
Southeast Portland is full of love. Lovely parks, lovely homes, lovely people from all walks of life. You'll see young familes exploring, cute couples biking on tandems, hipsters, musicians, artists, cute shops, makers, sex shops, Asian food, great parties...everything you need and want in a mid-sized city.
Cocktails and Dessert:
Most of SW is missable and can be done in half a day. There isn't much to see here than can't be seen and done in other cities. Here are a few specific traditions you shouldn't miss out on if you have extra time:
Many tourists come to Portland specifically to check out the beer scene, so I've include it in its own section. If you love good beer, check out:
If you're just here for the weekend, you may only have one big night to go out drinking. In that case, make it a priority to at least get one drink down the hatch at these unforgettable, world-class establishments:
Below are some sources worth checking out before your big trip. All of them have great recommendations, however, I didn't source directly from these lists because none of them were quite Mint & Mirthy enough. They play into a bit of a tourist mindset, rather than allowing you to live like a local.
Check them out for additional perspectives, but don't get overly committed to any one particular thing. Have fun, let yourself get lost in our gorgeously bikeable neighborhoods, and get ready for the trip of your life!
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