Trailblazing

What to See and Do in Portland

Where to start in the Pacific Northwest's other signature city. Plus, stops off the beaten path.

By Allison Williams and Ramona DeNies

Here in Seattle we love Portland the way we love a rambunctious little brother. A few hours south on I-5, the Rose City seems to excel in ways our own metropolis doesn't—with central gardens, quirky old mansions, and aggressively quirky traditions. We gathered the best bucket-list attractions and other favorites off the beaten path.

10 Popular Things to Do in Portland

Forest Park

One of the largest city-owned wilderness areas in the country: a 5,100-acre, fir-studded blanket that cradles some 80 miles of trails and more than 60 native species of mammals and 100 species of birds, all within yodeling distance of a city of more than 500,000 people. Try entering at the Audubon Sanctuary for walks to a crumbling stone house and a 242-foot fir tree. 

Portland Farmers Market

It boasts a whopping five locations, but the Saturday flagship market at Portland State University showcases the city at its most bountiful. Buy produce—like a rare Catalan onion almost never seen in the U.S.—and fresh eats, like grilled peaches topped with crumbling cheese and huckleberries. Shop hungry. 

Oregon Historical Society Museum

The displays inside the downtown's history collections range from a pickup truck to a recreated MAX car, plus artifacts from the Oregon Trail (the famous wagon route, not the game). Temporary exhibits dig into local phenomena, like Pendleton Woolen Mills or Oregon skiers.

International Rose Test Garden

They don’t call this Rose City for nothing—the terraces of flowers in this giant garden inside Washington Park represent pure, official strains of the flower, strictly controlled but casually beautiful. A giant grassy amphitheater sits among the 10,000 or so roses, and pocket gardens, like one dedicated to flowers mentioned in Shakespeare, wait to be found behind hedges. 

OMSI

No one actually calls it the Oregon Museum of Science and Industry (“OMSI,” pronounced OHM-zee, is much more fun to say), but nearly all visitors fit in a stop with the hands-on science toys in the old turbine hall, the planetarium, the giant theater, or the retired battle submarine out back that once starred in The Hunt for Red October.

Pittock Mansion

Henry and Georgiana Pittock went from wagon-train pioneers to Portland city pillars, at one time owning the Weekly Oregonian and organizing local philanthropy. Their grand house overlooking the city from Forest Park has Turkish, English, and French elements, plus a hydraulic shower with horizontal sprays and a temperature tester for the toe. 

Powell’s City of Books

A veritable Portland landmark, Powell’s is known far and wide as the largest independent store for new and used books in the nation. This bibliophile's fever dream takes up a full city block and is three stories tall—less a shop and more of a cathedral to the bound book, with plenty of Portland-branded socks, journals, and doodads for sale as well.

Voodoo Doughnut

You can do everything at the central outpost of this grungy-on-purpose 24-hour dessert emporium: people-watch, clog your arteries with a Cap'n Crunch doughnut, get legally married (doughnuts included!). And while after-hours lines fill with everyone from innocent-eyed out-of-towners to glassy-eyed truck drivers and wired purple-haired teenagers, there’s always the voodoo doll-shaped treat to poke in frustration before eating.

Portland Art Museum

Located on the South Park Blocks—a kind of long and skinny pedestrian mall that cuts through downtown—the city’s art museum boasts a century-plus of history and an extensive collection of Northwest and Native American art. Outdoor sculptures surround the grand modernist building. 

Oregon Zoo

The oldest zoo in the Northwest hosts 1.6 million visitors a year, but that doesn’t mean it rests on its laurels: A new aviary opened to house California condors, and an improved elephant habitat claims to be the biggest indoor elephant home in the world. Pick a favorite animal or two—polar bears, lions—since the zoo is too large to take in on a single visit; the Penguinarium, home to one of the most endangered species of penguin, is probably the most fun to say aloud.

7 Less Popular Things to Do in Portland

Pine Street Market

From maca and goji berry smoothies at Kure to Olympia Provisions’ Wurst fries and Salt and Straw’s Wiz Bang sundae bar, downtown’s upstart market is a food hall that might rival Pike Place Market. Opened in May 2016, Portland’s original upscale food court kick-started a citywide trend. This is prime people-watching; think Kitchen Confidential meets Portlandia. For help, consult Portland Monthly food critic Karen Brooks’ Pine Street cheat sheet.

Breakside Brewery

Craft beer isn’t always micro. Take the glittering Slabtown location of Portland’s award-winning shrine to beer: three stories, including one rooftop bar, of sudsy paradise—plus a reputation as a Hop Lab for the house-only experimental quaffs.

Portland Japanese Garden

In the forested hills high above downtown, Washington Park’s renowned Japanese Garden went next level in the late 2010s, unveiling a stunning $33.5 million upgrade from star architect Kengo Kuma, designer of the Tokyo Olympics national stadium. (In town, Kuma also led an airy redesign of beloved farm-fresh spot Shizuku.)

The Portland Japanese Garden holds eight distinct botanical spaces within its borders.

Image: Gage Murrey

Pendleton Woolen Mills

For more than 150 years, Pendleton has cornered the classic western-wear market. Further raising the profile of this family-run Oregon company: collaborations with Star Wars, Marvel, and the National Parks Service. While it’s based in northeastern Oregon, the company has a 3,000-square-foot flagship store in downtown Portland on Park Avenue West. Remember, no sales tax.

Society Hotel

Just a jig south of Union Station, the circa-1881 Society building once served as a safe haven for transient sailors. Bunkhouse accommodations channel that past in this artfully minimalist new iteration. A street-level coffee/cocktail bar offers local roasts and spirits; a top-floor deck offers sweeping views of Portland’s Old Town district.

Wildfang

Iconic in the mid-2010s, “Wild Feminist” T-shirts popped up everywhere—on Evan Rachel Wood, at Coachella, front and center at a Pantsuit Nation flash mob. They’re classic Wildfang, the tomboy-inspired line from Portland designer Emma McIlroy, who also makes signature clothing in bold patterns; the downtown flagship does personalized styling appointments.

Tilikum Crossing

The City of Bridges gained a gorgeous landmark with its newest span, the South Waterfront’s white-cabled—and car free—Tilikum Crossing. From downtown, catch the Portland Streetcar to cross the bridge to OMSI, then the Eastbank Esplanade, and loop back up to East Burnside.

Tilikum Crossing was built for streetcars, cyclists, and busses—but no personal cars.

Image: Cole Keister 

Composite image: photos ARTYOORAN (Powell’s), Agave Photo Studio (Voodoo), Jess Kraft (Old Town) / Shutterstock.com; Ameen Fahmy (Rose), Everett McIntire (Oregon sign), Uday Mittal (Mt. Hood), Wesley McLachlen (Painting) / Unsplash.com

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