I KNOW—because you newbies say it constantly—that Portland isn't that big. Navigating this terrain won't be all that intimidating, but natives judge you based on where you settle and hang, so don't fuck this up! Here's a handy list of go-to areas and how to vibe when you're there.
The heart of the city! Portland's living room! Unfortunately, downtown Portland is an area that, while beautiful and easy to navigate, is likely to shut down early and appear mostly dead on the weekends, when the office stiffs are drinking where they live. It's expensive to live here, although you could get by fine without a car, so that's nice. Food carts are everywhere. A lot of places smell like pee.
This area is a big draw for out-of-towners, yet remains a place where locals wanna eat and shop, too. The neighborhood has been dense for years, which spared it a lot of (but not all of) the glass-and-steel condo infiltration that's happening over on Division. It's got the Bagdad, Red Light, and even a Powell's! I hate people and still love hanging out here. But for the love of Christ, don't ride your bike on SE Hawthorne.
This is the only neighborhood with a "the" in its name. Fancy! Oh, and that reminds me—when you say where you live, it's always number street (without directions), then name street, like "10th and Burnside." My darling friend who moved here last year kept saying "SE [number] and SE Stark" and I told her she sounded like a fool from New York City, which she was. Anyway, the Pearl... the Pearl is whatever. Expensive. Shiny. Is it important to be walking distance to galleries and a P.F. Chang's for $2,500 a month? Then you'll love it.
Here is a delightfully dense residential neighborhood in Inner Southeast. I put it on this list because it's where I got my first apartment in 2004. It was a one-bedroom with huge windows and an illegal balcony in a converted mansion. I paid $500 a month. You should know that only a decade ago, this was a city where a 22-year-old making $10 an hour could live alone in a really nice place.
This is where I live now, as do many of my friends in their 30s who scraped together enough cash to buy, but not enough to buy somewhere fancy. Great old-timers, lots of young families, and still plenty of grit. It's a lot more ethnically diverse than other neighborhoods. Best Asian food in town. More than one Russian grocery store. And the jewel in our humble crown is the newly opened Portland Mercado, which I highly encourage you to visit even if it means the rest of us will have to wait in line.
This is a relatively small commercial street that's charming as fuck. It's also (along with NE Alberta/Killingsworth) emblematic of Portland's gentrification. Check it out because there is some good art and really good food, but visit the light bulb store and chat with the lady who works there and don't be oblivious to what was lost—or rather, displaced—when the strip got desirable.
This little pocket starts around Voodoo Doughnut and ends at the Pearl. It is home to a lot of homeless people, as well as a lot of seedy Portland history. Fun fact (that I learned from my buddy Joe, who also writes for this paper): The Shanghai Tunnels were not a real thing. Don't perpetuate this myth or you'll give him a hernia. You may use Voodoo Doughnut as a point of reference for exactly one month after arriving here, and no longer.
This part of town is the slightly nicer version of FoPo, but practically in Washington, with established businesses and a newish influx of younger families. I would live there instead of in Southeast if it weren't so goddamn far from everything I need to do. Seriously, how is it so far away? And why can't you drive faster on Columbia?
Last Thursday is a clusterfuck that many people enjoy in summer. Not many businesses on this street have been open longer than 15 years. More bars than brunch spots, which is a plus, but too many places trying to sell cashew-something as a replacement for cheese. Get real, guys.
NW 23rd/NW 21st
I once dated a guy who bragged about owning his own place over there, and then I found out his parents bought it for him. I feel like that's characteristic of the neighborhood. As bridge-and-tunnel-esque a crowd as Portland gets.
Goose Hollow/Southwest Hills
Literally all bridges and tunnels.
More Newcomers' Guide Articles:
Welcome to Portland!
Rain! Rain! Rain! Rain!
A Portlander's Pronunciation Guide
A Newcomers' Guide to Making Friends
Portland Free Stuff
Getting Around Town
Finding a Place to Live
How to Apologize for Moving to Portland
Bicycle Death Traps
Portland History 101
Portland Myth Bustin'!
Portland Tourist Traps