Teeming with eccentric museums, haunted house bars, and more pinball machines per capita than anywhere in the country, Portland, Oregon, is a city so intrinsically quirky that it makes Portlandia look like a documentary. The infamously offbeat city has long been a mecca for hilariously specific restaurant concepts and singular thrills, like caviar-fueled queer dance parties, potential buried treasure and cinnamon roll-exclusive bakeries with pastries so extravagant they make Cinnabon look like Weight Watchers, but Portland’s developed a grittier edge of late.
As one of the whitest major cities in America, it became a hotbed for riots and anarchists during the Black Lives Matter protests in 2020, leaving downtown in a state of disarray amidst pandemic-induced closures and social justice revolution. But despite the lingering grit, Portland’s reputation as one of the nation’s most progressive metropolises forges forward. Nowadays, the downtown area bustles anew, a Black Lives Matter-themed summer camp champions youth activism, and business is booming. Through it all, with its surplus of whimsical oddities, we’re thrilled to report that Portland is just as weird as ever.
What to do
Like any global, culturally rich city, you can expect to find sprawling art museums and a Jurassic Park-sized zoo in Portland, along with 70 miles of trails in the 5,156-acre Forest Park and the International Rose Test Garden, where new rose varieties are tested amidst a floral sea of 10,000 bushes. And it only gets wonkier from here.
The Freakybuttrue Pecularium is a satirical horror-themed museum, gallery and shop with exhibits on everything from alien abduction and Krampus to rotary phones. The small museum only has a few rooms, and children and squeamish individuals are cautioned against entering, but if you can get over the creepy Bigfoot figurine and unnerving puppet, there’s a lot to laugh at (like a display on spontaneous human combustion that lists “feeling like kindling” as a symptom for bursting into flames). Down the street in Nob Hill, Paxton Gate is a macabre store that keeps the creepy theme going with all the fossils, framed insects, taxidermy and turkey toes you never knew you needed.
For something a little less morbid, spend time at Powell’s City of Books, a veritable Mall of America for bibliophiles. Occupying an entire block downtown, with nine rooms and 1 million books, it’s among the largest bookstores on Earth — a treasure trove of classic tomes and rare reads.
The only thing bigger than Powell’s in Portland is the city’s surprisingly robust pinball scene. As the “center of the pinball galaxy,” with more pinball machines per capita than anywhere in the nation, this is a city that takes its vintage arcade gaming seriously. Found in bars throughout town, pinball is so prolific that there’s an app that helps you find the closest machine — basically Tinder for arcades. Or you can just hit up Ground Kontrol arcade bar, home to countless pinball machines with themes like Godzilla, Iron Maiden and Pirates of the Caribbean.
Afterwards, book a massage in a tiny house. Because Portland. Right in line with the city’s prominent food cart culture, Tiny Massage Cart is Portland’s first massage cart, where massages are performed in a cozy little cart, down a bucolic gravel path, in the Alberta Arts District.
Another leisurely option is the historic Academy Theater in Montavilla. Open since 1948, the vintage charmer is a cool place to see the latest blockbusters, classic films and kitschy screenings of random cult favorites like Anaconda. History aside, the theater differentiates itself by offering food from nearby restaurants, like Flying Pie Pizzeria and Miyamoto Sushi, along with kombucha, beer and wine. And feel free to imbibe, because the theater offers on-site babysitting during movies on weekends.
Where to eat and drink
Portland’s food scene is world-class, home to some of the finest culinary talent and envelope-pushing concepts unafraid to think outside the box in a city that welcomes invention. It’s also hilariously, audaciously specific, with one-of-a-kind bars and restaurants so distinct you wonder if Fred Armisen and Carrie Brownstein bankrolled them as jokes. But despite the occasional theatrics, it works. As a major food city, Portland proves it can innovate on a national stage while not taking itself too seriously. There’s room for both fancy foie gras dumplings and eerie restaurants decorated with fake cobwebs and demonic ravens.
Case in point, Ravens Manor is a dark, billowing downtown restaurant that conjures Edgar Allan Poe vibes with glowing cocktails in lab beakers and a dessert called Screaming Ghosts, with fried-to-order beignets shaped like “howling souls.” The soaring space leans into the haunted house motif with flickering candles, dusty cobweb-clad books and a downstairs area — which guests are free to explore — that looks like something from Saw, complete with banging doors, gnarly laboratories and bloody sheets. If you need some liquid courage, just throw back a Brain Hemorrhage Shot, which as the menu describes, “looks like brains, tastes like peaches and cream.”
Across the river, on the Central Eastside, the spooky scene keeps apace at Creepy’s. Living up to its name, with enough creepy clown decor for another It sequel, the bar crams every inch of its walls and shelves with the kinds of stuffed animals, dolls and taxidermy that look like they definitely become sentient after hours, like some kind of nightmare Toy Story. That being said, the cocktails here are the real deal, from tinglingly tart Pickletinis to dark and smooth Black Manhattans. There’s also a selection of smash burgers, including veggie versions, which are pure Americana comfort.
Beyond the creepiness, other bars and restaurants channel their own weirdness via historic architecture, eccentric eats and dollhouse-perfect coffeeshops. One example is Steeplejack Brewing Company, a former church from the early 1900s that’s been transformed into a family-friendly brewpub in Sullivan’s Gulch. The ornate stained glass and lofty craftsman-era chapel remain, but instead of drinking the blood of Christ, you’ll be drinking altbiers and Vienna lagers. Food-wise, jerk chicken sandwiches and mashed potato croquettes are far tastier than the Eucharist.
“Vegetables will be slaughtered” is the battle cry — and pithy culinary ethos — at Fermenter, a fiercely farm-to-table restaurant in Buckman. As a kombucha pub, plant-based deli and self-described “beneficial bacteria emporium,” it’s a place that takes fermentation so seriously it’s in everything they serve, from beer and wine to bread, cheese, tempeh, kimchi and koji. Using local and seasonal ingredients, the dynamic menu runs the gamut from tempeh patty burgers with dill kraut and sunflower chive cheese to miso-braised beans with a punch of cumin. Peep their Instagram for specials so vibrant they’d make even the most cynical carnivore drool.
Equally as vibrant, but decidedly more meaty, Eem is a clamorous Thai barbecue restaurant and quasi-tiki bar where tropical frozen drinks share menu space with fun, flavorful — and frequently fiery — plates like pork belly burnt ends, hot cauliflower with chili jam and white curry with brisket. Portland has an abundance of Southeast Asian restaurants, and Eem feels like a transportive vacation to the jungles of Chiang Mai or the islands of Phuket. Just close your eyes and slurp some Drugs, which is the name of a standout frozen cocktail made with aged rum, pineapple, amaro, coconut cream and orange.
Coffee culture is a thriving industry in Portland, from famed homegrown titans like Stumptown Coffee Roasters to new imports like Proud Mary, a roaster out of Melbourne that selected Portland for its first location outside of Australia. Then there are the myriad neighborhood cafes, in all their twee glory, serving singular sips more akin to milk-based mixology than your standard barista fodder. Super Joy Coffee is a precious nook of a cafe slinging sea salt taro lattes and pink cardamom milk with the daintiest latte art, while just up the street, Never Coffee looks like the kind of chic, twee space you’d expect to see in a Wes Anderson movie. Draped in tints of soft green and pink, meticulous lattes layer flavors like yuzu, sansho pepper, burnt sugar, Oregon salt and coconut cream.
Doughnuts are to Portland as bagels are to New York City. From bakeries to dessert menus, they come in all different flavors, sizes, and shapes — including doughnuts shaped like voodoo dolls being stabbed with pretzels. One novel take is the mini prix fixe offerings at HunnyMilk, a cute cafe serving a menu of sweet and savory doughnut-inspired dishes. Eschewing traditional flavors and techniques, the menu includes the Monte Cristo-Nut, a cornflake-French toast fritter with manchego fondue, green pepper marmalade, and ham, and Nutella-dipped red velvet doughnut holes with double chocolate crémeux and glazed bananas.
Where to stay
Fortunately, there are no creepy clown-themed hotels in Portland (yet), but lodging options are no less unique. Rest your head at the KEX Hotel, a self-described “social hotel” that originated in a defunct biscuit factory in Reykjavik (“kex” means biscuit in Icelandic, adorably), which opened its first U.S. outpost in the Central Eastside in 2019. The design-driven property’s accommodations are similar to a hostel, with a mix of artful private rooms and communal bunk rooms. Amenities include a brand new rooftop bar, The Sunset Room, and a ground-floor restaurant called Pacific Standard, where the espresso martinis are so low-key strong that there’s a two-drink max. And in a move that feels very Icelandic, the hotel also has a sauna, available by reservation from 6 a.m.-11 p.m.
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