Pioneer Courthouse Square

For most visitors, downtown Portland is just the launchpad from which they explore the city’s patchwork of neighborhoods. But amid the central city’s staid maze of banks, federal buildings, and big-name stores hide high-end, locally owned boutiques; fancy, semi-secret bars; old-school Portland weirdness and some of city’s best food cart pods. 

Kick off your day savoring a cup of joe and some seriously good baked treats at Courier Coffee Roasters, while the counter staff plays cuts from a vast vinyl collection, hip-hop to Bach. 

For sit-down fare, find sustainable catches at Bamboo Sushi or try French-Scandinavian “pastry luncheonette” Maurice holds first-rate quiche to world-class brioche plumped with fat berries while restaurant sibs Lardo (gutsy sandwiches) and Grassa (housemade pastas) sate all your carb cravings.  

Liberating womenswear one fitted blazer at a time, Wildfang’s band of modern-day Robin Hoods raid men’s closets and dispense the styles they love, from wingtips and wildly patterned suit pants to exclusive content and inspiration, like that Wild Feminist T-shirt you’ve been seeing, oh, everywhere. 

Portland has danced, shouted, and bounced on the Crystal Ballroom’s trademark “floating floor” for more than a century—a live music and dance venue as storied as any museum. Owned since the 1990s by the McMenamins brothers (the region’s preeminent beer + restoration experts), the vividly decorated theater’s mainstage has played host to acts from ’60s-era Grateful Dead and Ike & Tina Turner to Sleater-Kinney and Future Islands. Downstairs, Lola’s Room deploys ’80s Video Dance Attack dance parties and smaller shows weekly. 

Venturing into the heart of downtown, cultural entertainment ranges from people-watching and pop-up festivals at Pioneer Courthouse Square to combing through music bins at 2nd Avenue Records to underground mini golf at the black-lit, pirate-themed Glowing Greens. Or, take in a concert (post-pandemic, of course)—perhaps a mellow, sit-down affair at the Arlene Schnitzer Concert Hall or a serious stomper in the purple-walled sweatbox of the Roseland Theater. 

Working downtown? It’s only a matter of time before you settle on a few home bases. For coffee, choices include traveler-packed Stumptown in the Ace Hotel, Courier (see above), the sneaker-ific Deadstock in Chinatown, and innovative Water Avenue. For lunch, a stop at the Pine Street Market food hall can give a quick intro to some local culinary stars before you branch out on your own. 

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