Portland is such a cool little city. Or at least there are a lot of people who think they are very cool. I don’t want to define cool, but sometimes it must be done. First of all, there’s “good” cool and “bad” cool. Good cool is first, being one’s wonderful self, and second, having some interesting interests and reasonable semblance of good taste. Bad cool is not being yourself, following fads aimlessly and looking down on anyone who you decide is not cool.
Portland is full of both good and bad cool people. There a few trendy, popular consumer districts to go find cool people. Some look pretty cool. A few act cool; a bunch don’t. But hey, what city would be cool without its cool people?
The obvious, well known and tried and true cool areas are around the following streets: Northeast Alberta, Southeast Belmont and Hawthorne and Northwest 23rd and 21st. This list is not exhaustive; there are others in Southeast, St. John’s (sort of) east Burnside, etc. Downtown is cool enough, but too big and varied. You see some cool people, but also many business people and city-type business schlock. Campuses are traditionally on this list. Maybe Portland State will make it some day.
I’ll focus on the hot stretches of these cool zones, where most foot traffic and people congregating take place. The point of this story is to tell you where to watch the “cool” people do their thing and where to hang out. If you want cutesy gifts, look near where you hang out and watch the cool people. I will also tell you about “what the cool people’s problem is.” So let’s geographically stereotype and make those broad generalizations, just in time for spring break boredom.
Hawthorne is definitely Southeast Portland’s coolest stretch of pavement. Cool people walk around, hang out and shop in the cool shops. The cool starts around 25th Street, give or take five blocks. It then stretches East for about a mile. Hipsters, hippies, curious patrons on odd tourist families crowd the streets, stores and eateries along the street. Hawthorne boasts the regular mix of hip clothing, oddities, music, coffee and food establishments.
In the past few years, The Red Light, at 3590 S.E Hawthorne, has become the bastion of hip used or “vintage” clothes for cool kids. The huge store has a grip of great threads, lots of cool people looking through racks and generally prices on the higher end. For more hip threads the Buffalo Exchange is across the street and around the corner at 1420 S.E. 37th. Great record and CD stores include the eclectic Reverb (3623 S.E. Hawthorne), indie-rock haven Jackpot (3736 S.E. Hawthorne), and blues-centric Crossroads (3130 S.E. Hawthorne).
There a many places for food and coffee, all filled with various percentages of the people mentioned above. The best of the coffee shops is the Fresh Pot, inside Powell’s (3723 S.E. Hawthorne). Good music and coffee and good luck finding a seat, because it’s always super crowded. The McMenamin’s empire holds residency at the Bagdad theater (3702 S.E. Hawthorne). It’s a beautiful restored old theater and restaurant that runs cheap movies and sells beer.
Northwest 23rd, nicknamed “trendy-third” is in close running with Hawthorne for the coolest, hippest and trendiest street in Puddle town. Two blocks down, 21st is rapidly approaching its neighbor’s density and popularity. Starting at Burnside and running many blocks north is a stretch of trendy places to shop and eat.
The best thing about this stretch is the buildings themselves. Many shops reside in old townhouses and interesting buildings. Shops are packed together tightly and there are many to see. The worst thing is also this density. There are gaggles of people and too many cars aimlessly circling because there is never any place to park.
The neighborhood does have that big city cool feeling, at least sometimes. The area used to be an average neighborhood with average homes and average people. Then seemingly overnight, it became too cool for school. There are many places to eat expensive food and not enough to eat cheap. Lots of hip clothing and cute gift shops abound. For food, definitely check out Escape From New York’s (622 N.W. 23rd) pizza. It almost tastes like New York. Coffee Time (Northwest 21st and Hoyt) is the hub of cool coffee shop hangouts.
These Northwest strips can be interesting for a couple seconds, every once in a while. They are generally filled with too much cool (yes that is very possible) and too many tourists. You have to walk very slow and try hard not to get annoyed.
The general breakdown on Hawthorne and Trendy-third consists of Hipsters intermingled with tourists, hippies and yuppies. The tourists are usually noticeable. They look like tourists, excited to be on Portland’s famous streets. Hippies are usually lounging about with their dogs, being hippies. The fashionable yuppies are sauntering around in their Prada sportswear acting like superior poster children who wished they lived in L.A. or NYC. The suburban yuppies muscle S.U.V.’s along the street and push everyone else out of the way. Hipsters hang about looking hip, only talking to other cool people. Then there are the people who hang out on the street spare changing, entertaining or just sitting and staring. They are the coolest of all.
Southeast Belmont is like Hawthorne junior. The densest stretch is between 33rd and 36th Avenues. Eateries, boutiques, bars and cute gift stores are in slightly shorter supply than big daddy Hawthorne. The Paradox Palace Cafe (3439 S.E. Belmont) has some great vegetarian food and a fun atmosphere. All kinds of cool people stop in to eat. To get a drink at night and check some neighborhood flavor, check out Belmont’s Inn (3357 S.E. Belmont) and the Vern (30th and Belmont). Belmont’s has a good mix of people, some who are cool, many who are annoying. Lots of pool, a decent jukebox and a really plain, boring atmosphere. The Vern used to be an average cheap dive. Now it can be a little scary sometimes. Lots of skaters, bike messengers and local hippies. Speaking of local hippies, Belmont street is a perhaps the best place to watch them. Some of them are OK, even cool, but many seem a little too fuzzy-headed to deal with. There are a few good eateries and pizzerias like It’s a Beautiful Pizza (3341 S.E Belmont) and a good handful of places to get your girlfriend things like African masks, rubber stamps and bondage harnesses.
Years ago, when I first moved near Northeast Alberta Street, someone who lived there told me that 10 years ago it was one of the most dangerous places to live. I saw drug deals in front of my house, and it was occasionally noisy with rowdy people, but the area never felt truly unsafe, at least during the daytime. It was in the process of becoming gentrified. Hip, trendy businesses were moving in, property value was going up, and the cultural diversity became more homogeneous. Watch as this continues to happen here and elsewhere.
Start your cool-people watching at around 15th and end at 33rd. I would recommend snacks at the Alberta Street food Co-op (1500 N.E. Alberta) and a plate of American food at the kitschy Chez What! (2203 N.E. Alberta) or some great vegetarian diner food at the Vita Caf퀌� (3024 N.E. Alberta). The Chez also now serves booze in their newly annexed Whatever Lounge. There are also a couple places to get real Mexican food. I prefer La Sirenita (2817 N.E. Alberta).
There’s much, much more, so good luck with your search for cool people and entertainment.