Now that you can afford more than ramen and Rainier, show your former roomie the trendier side of Portland.



Jupiter Hotel  This mod hotel’s 81 rooms come with bikes ($35 per day to rent), and with plenty of nearby cycling streets and lanes, your pal has an ideal home base for a two-wheeled exploration of Portland cool. From $129

Le Pigeon  It never gets old. Sit at the bar, order the chef’s five-course tasting menu, and let Gabriel Rucker, the punk-French cook who put a bird—and a Beard Award—on Portland’s culinary scene, blow your #$&%ing mind. 1 block

The 811 Building  Soak in all things vintage, handcrafty, and indie-avant-artsy at Haunt, Sword & Fern, Nationale, and the Adams and Ollman gallery. 2 blocks

Rontoms  Ping-Pong on the back patio. Winning’s not required. Trying is. 2 blocks


Consider these drinking establishments for a variety of hipster subspecies. Select the best fit. 

The Bearded Midwestern Transplant: Beer
Go for the 95 unique brews. Stay for the unbelievable amount of vintage beer kitsch.

The Designer: Dig A Pony
Where Adidas- and Nike-ites make nice (and pretty). 

The Rocker: Bunk Bar
Massive, messy sandwiches? Check. Massively loud live music? What?! 

The Sophisticate: Distillery Row
Five boutique booze makers. Because upscale hipsters understand what they’re chasing with Pabst.  

1 Mile • INNER SE

Colonel Summers Park  You don’t have to join the kickball game being played in perpetuity here, but you do have to watch, at least for a minute.

1.2 Miles • OLD TOWN 

Ground Kontrol  Throwback video games. Beer. Need we say more?

Low Brow Lounge  Baby hipsters were born (and probably made) here back in the 1990s.



1.5 Miles • INNER NE 

Hollywood Vintage  Because the only thing cooler than angular eyewear is really old angular eyewear. The hat selection is also particularly fetching, in a midcentury-modern way. 

1.5 Miles • DOWNTOWN

Tender Loving Empire  Retrieve your ironic-but-earnest Portland 
souvenir here. 

Public Domain  We’re the only town in America that could possibly host coffee happy hour: $2 espressos with a shot of Pellegrino to wash ’em down. 

Animal Traffic  For all your vintage Pendleton needs.


Tannery Bar
Image: Kate Madden

The Tannery Bar  Any place that hangs a giant neon sign for longneck Rainier out front automatically qualifies as ironic. The extensive vinyl collection, well-crafted cocktails, and excellent small plates (we recommend the Monte Cristo) make this cozy spot actually cool.




Mississippi Studios  Portland’s natty nano concert venue.

Mississippi Marketplace  The Big Egg, Native Bowl, and German beer bar Prost marked the evolution of Portland’s food cart scene in 2009. 

Radar  Discover delicious Scandinavian-style brunch items like baked eggs and smoked bluefish pâté at this tiny spot with fancy cocktails designed by one of the bartenders at NYC’s legendary Death & Co.

Albina & Sumner A record store (Mississippi Records), modern art (Museum of Modern Art), and a retro bar with a stuffed dead animal (Red Fox Bar), all on one block. The only thing more twee than this trifecta is brunch spot SweeDeeDee around the corner. 

3.3 Miles • NOPO 

Sunset at Skidmore Bluffs Behold the beauty of the sun sinking over the city, Forest Park, and a vaguely industrial landscape. Disregard the sneers from the skinny-jeans people who think they “found” these NoPo bluffs first. Keep your tallboy discreet. 




Anywhere between 10th and 33rd, but especially Barista CaféAmpersandMonograph Bookwerks, and the Bye and Bye, where the combination of fat mason-jar cocktails and skinny vegans proves incredibly entertaining.



8.6 Miles • ST. JOHNS

Division Leap  St. Johns’s veritable emporium of impossible-to-find zines, rock-show posters, and strange outsider art from the ’60s, ’70s, and ’80s is open by appointment only. (Consider taking one of the Jupiter’s two on-site ZipCars for this venture.)


Talking Point In 1897, Sullivan’s Gulch held Cycle Park, an amphitheater filled with bike tracks and a carnival-like atmosphere at NE 18th and Halsey.