Portland: The City That Won the Coin Toss

Most American cities would kill for a slogan as sticky as "Keep Portland Weird." The bumper stickers started appearing in 2003, the work of a local music shop owner trying to stem the tide of chain stores moving into the Mississippi Avenue corridor. They worked, after a fashion. The chains came anyway, but the weird stayed too, calcified into something locals defend with the ferocity of a family secret.

Portland's weirdness has deeper roots than the slogan suggests. The city was built by people who got chased out of everywhere else. The original plat was won in a coin toss between Francis Pettygrove of Portland, Maine and Asa Lovejoy of Boston. Pettygrove called the flip correctly in 1845, and the city got its name. Lovejoy walked away muttering. That founding moment—arbitrary, slightly bitter, dependent on chance—set a template Portland never quite escaped.

Start at the Oregon Historical Society downtown. The museum's permanent collection includes the actual penny Pettygrove flipped, displayed like a religious relic. More interesting is the "Oregon Voices" exhibit on the second floor, where oral histories trace how successive waves of migrants remade the city: loggers in the 1880s, shipyard workers during World War II, hippies in the 1960s, tech workers in the 2010s. Each group arrived convinced they'd found the place that would accept them. Each reshaped Portland in their image while complaining about whoever came next.

Walk east across the Burnside Bridge to the Buckman neighborhood. The buildings here tell the story of Portland's industrial boom and subsequent neglect. The Burnside Bridge itself, built in 1926, is a rare example of a double-leaf bascule drawbridge with one operating system—a distinction meaningful only to bridge enthusiasts, but emblematic of Portland's habit of preserving technical oddities. The city spent $800 million preparing to replace it, then voters rejected the funding in 2024. The bridge stands, rusting slightly, operating on machinery installed during the Hoover administration.

The Central Eastside Industrial District, below the bridge's east landing, was until recently the kind of place taxi drivers warned you about. Now it houses distilleries, coffee roasteries, and the occasional tech startup. The buildings are brick, mostly, with loading docks that now serve as patios. Base Camp Brewing occupies a 1920s warehouse; their patio features a fire pit and permanent camping equipment, including a tent that hasn't moved since 2012. The beer is adequate. The space captures something essential about Portland: the insistence that wilderness and urban life can coexist, even if the wilderness is simulated.

Powell's City of Books, occupying an entire city block on West Burnside, is the obligatory stop. The claim to being the world's largest independent bookstore holds up—over one million new and used books spread across color-coded rooms. The staff recommendations, handwritten on index cards, are genuinely useful in a way algorithmic suggestions never are. A clerk in the Gold Room (science fiction) once told me that Ursula K. Le Guin shopped here anonymously for decades, asking staff for recommendations and never revealing her identity. I have no way to verify this. The story persists because Portlanders want it to be true.

The Pearl District, northwest of Powell's, demonstrates what Portland became and what it fears. Twenty years ago this was warehouse country; now it's glass condos and $14 cocktails. The satirical slogan "Keep Portland Beige" started here. But walk the side streets. The Everett Street Lofts, a 1910 warehouse converted to artist studios in the 1980s, still operates. The ground floor houses a print shop where a man named Dennis has been setting metal type since 1987. He'll show you his collection of wood type blocks if you ask. Most people don't ask.

Portland's food cart culture developed as a workaround. The city made street vending illegal downtown for decades, so entrepreneurs parked trailers on private lots instead. The result is pods—clusters of food carts gathered in parking lots, each with its own microclimate of cuisine. The Alder Street pod downtown has over 60 carts: Korean-Mexican fusion, Iraqi kebabs, Senegalese thieboudienne, Portland's inevitable Thai food. The Nong's Khao Man Gai cart, now a brick-and-mortar restaurant, started here. The dish—poached chicken over rice with ginger sauce—became so associated with Portland that locals forget it originated in Hainan.

The Hawthorne District, across the Willamette River, was Portland's hippie heartland. It still is, sort of. The Baghdad Theater, built in 1927, shows second-run films for $5. The popcorn is real. The Bagdad Pub next door serves beer in pitchers and doesn't card aggressively. Further east, the Clinton Street Theater has screened "The Rocky Horror Picture Show" every Saturday since 1978. The shadow cast knows what they're doing. The audience knows the callbacks. The ritual has outlasted three generations of regulars.

Forest Park, five miles west of downtown, is the largest urban forest in the United States. Thirty miles of trails thread through 5,200 acres of second-growth Douglas fir. The Wildwood Trail runs the park's length, from the Oregon Zoo to the St. Johns Bridge. You can hike for three hours and emerge at a brewery. This is Portland's gift: actual wilderness accessible by public transit. The number 15 bus drops you at the Lower Macleay Trailhead. From there it's 30 minutes to the Stone House, a 1930s restroom building now covered in moss and graffiti. Locals call it the Witch's House. Children dare each other to enter at dusk.

The St. Johns neighborhood, at the park's northern edge, was an independent city until 1915. It still feels separate—a working-class peninsula where the bridge (Gothic, 1931, painted green) dominates the skyline. The neighborhood's main street, Lombard, has resisted the changes that transformed the rest of the city. The Proper Eats cafe serves vegan food that tastes like something. The St. Johns Theater shows movies for $7. The twisty streets above the business district contain houses built for shipyard workers in 1942, still occupied by their grandchildren.

Portland's relationship with its river has always been complicated. The Willamette bisects the city, but for decades it was treated as an industrial sewer rather than an amenity. The Tom McCall Waterfront Park, built on a former freeway in 1978, reversed that logic. Now the riverfront hosts farmers markets, dragon boat races, and the occasional homeless encampment sweep. The reality is messier than the postcards suggest. The water quality has improved enough that people kayak in summer. They still don't swim.

The Japanese Garden, west of downtown in Washington Park, opened in 1967 as a gesture of healing after World War II internment. It's considered one of the most authentic Japanese gardens outside Japan, which means something to specialists. The zigzag bridge forces evil spirits to slow down. The sand garden is raked daily. The view of Mount Hood, framed by carefully pruned maples, is the most photographed vista in Portland. The mountain is a dormant volcano that last erupted in 1782. Portlanders know this. They look at it anyway.

Mississippi Avenue, where the "Keep Portland Weird" stickers originated, is now the battleground for the city's identity crisis. The independent businesses that prompted the campaign—Mississippi Studios, Eutectic Gallery, the ReBuilding Center—still operate. So do the artisanal ice cream shop, the boutique selling $200 denim, and the whiskey bar with 300 varieties. The neighborhood's Black population, concentrated here since redlining confined them to this area in the 1950s, has been largely priced out. The irony is noted, occasionally, in alternative weeklies.

The best time to visit Portland is September, when the rain hasn't started and the summer crowds have gone. The second best time is any rainy Tuesday in January, when you can have the city to yourself and the breweries are warm. The worst time is August, when wildfire smoke turns the sky orange and everyone pretends this is normal.

Practical notes: The MAX light rail connects the airport to downtown for $2.50. The city is walkable but hilly; the street grid shifts 20 degrees at Burnside, a quirk that confuses even locals. Many food carts are cash-only. The Oregon Museum of Science and Industry, south of downtown, has a retired submarine you can tour. The guides are volunteers who served on it. Ask them about the kitchen. They have opinions.