Visit Portland's four corners to explore a cozy village, an urban wilderness, a new hipster haven, and the quirkiest street in town.
When explorers Meriwether Lewis and William Clark arrived on the verdant, forested land that is now Portland, they carried with them a small, silver-plated compass with two brass sight vanes, all contained in an elegant mahogany frame. If you want to go exploring in Portland today, you probably don’t need such a fine tool, but the city is still ruled by the compass—and neatly divided into quadrants by two intersecting lines on the map.
One line curves along with the Willamette River, dividing the west side of Portland from the east, and the other follows ramrod-straight Burnside Avenue, splitting the city’s north from its south. The result: four cities within a city, four lovely little worlds, each with its own wonders to discover, and an emblematic neighborhood begging for an exploratory stroll.
In Southwest, a Village on the Hill
Southwest Portland encompasses the city’s downtown, and even the business district here brims with the casual, funky splendor that makes Portland the place where—to quote the hit TV show Portlandia—“young people go to retire.” But the epicenter of the quadrant’s laid-back homeyness lies farther west.
If you travel away from downtown, over the hilly, winding streets that define the southwest, you’ll reach Multnomah Village. There, at Annie Bloom’s Books, easy chairs stand ready for you to curl up in, and the resident “literary cat” may slink along and purr in your lap. Across the street, Medley offers crisp British cheer at afternoon teatime. Lest things get a bit too stuffy, there’s an all-day breakfast menu starring rosemary-laced home fries and lemon–ginger–poppy seed scones. The Village also sees touches of urbane style: Switch Shoes and Clothing features delicate footwear from Israel, and Sip D’Vine stocks only Northwest vintages in its congenial carpeted lounge.
Still, what makes the place sing is its chumminess—and its grid-defying geography. “The streets here are so winding that people get lost driving,” notes Will Peters, a manager at Annie Bloom’s. “Then they get out of their cars and actually talk to each other."
In Northwest, where forest meets town
The city’s upper left corner is perhaps most famous for tony Northwest 23rd Avenue, where you can taste gourmet truffles at Moonstruck Chocolate Café or buy tiny tulle dresses at Duck Duck Goose. But the backdrop of the northwest quadrant is uninhabited wilderness: Most of 5,172-acre Forest Park lies within the district, as does its 30-mile-long Wildwood Trail. Access it from the Lower Macleay Trail, which wends through a fern-lined canyon and alongside frothing Balch Creek.
The trail descends onto Northwest Thurman Street, a thoroughfare celebrated by Portland science-fiction and fantasy author Ursula K. Le Guin. In her 1993 coffee-table book, Blue Moon over Thurman Street, Le Guin writes, “A street that ends in a forest—there is a magic there.” Her words ring true as you stroll through the hobbitish neighborhood.
At Dragonfly Coffee House, espresso machines hiss and steam in a small room a-jumble with comfy couches. Nearby, at Betsy & Iya, you can hear the in-house artisans hammering at their creations as you peruse an array of stylish accessories: art deco earrings, Ethiopian scarves, necklaces inscribed with Morse code, bracelets that mimic the city’s famous bridges.
The Peculiarium is, in contrast, a gallery and store specializing in eerie oddity. Gangster Al Capone’s “real safe” is on display here, along-side an ancient bottle of Invigorating Brain Cream. There are zombie-head Shriner masks for sale, as well as old View-Master slides and a ceramic bust of a bunny-suited man.
At Wild Wasabe, sushi chef David Song slices fresh albacore, salmon, and squid with lightning speed. Up the block, cookie shop Bluebird Bakers occupies a minuscule, wood-floored storefront. Try the chocolate chunk cookie, made with Belgian dark chocolate and sprinkled with sea salt. Like the shop itself, it’s so sweet that it seems conjured by fairies. [Editor's note: Bluebird Bakers closed their Thurman Street shop shortly after this story went to press.]
In southeast, an original hipster haven
Along Hawthorne Boulevard, you can find Jackpot Records, a branch of Powell’s Books, and the old Bagdad Theater, all hunkered down on the same block since the mid-1990s. But of late, a fresher, more intimate artisan scene has emerged just a few blocks north on Southeast Belmont Street.
At Twill, a women’s boutique purveying a large selection of local clothes, everything is alive with a gossamer whimsy, be it the small star-shaped earrings fashioned out of rattlesnake bones or the wrap dresses printed with birds or roses. Shop clerk Tylar Avery says, “This is a place where clothes makers will actually bring in a dress and say, ‘What do you think of this? I’m still working it out.’”
Next door to Twill is arguably Portland’s prettiest nightspot, Circa 33. High shelves of bottles, accessible only by ladder, tower above the dark wooden bar and glimmer beside a silver mirror in a lustrous amber light. In the next storefront, Blythe & Bennett Records takes it old school, selling a vast range of vinyl LPs, everything from Foreigner to Billie Holiday.
Nearby is the divine Suzette creperie, where pastry visionary Jehnee Rains exercises her wry taste for miscellany. There’s an ancient typewriter and an adding machine in the front window, and seating includes both red-leather theater chairs and church pews. The exquisite crepes, meanwhile, are at once curious and cosmopolitan. One called Goat Fig Pig combines goat cheese, marsala-soaked figs, and prosciutto. An African take on smoked salmon comes topped with a roasted garlic–chickpea spread and harissa.
Further along, find tranquillity at the Tao of Tea, a teahouse that feels like a Chinese garden. Buddha statues abound and a small, trickling water fountain babbles away. The infusions come in ceramic pots warm to the touch, and just smelling them gives you visions of the places the tea leaves grew—Sri Lanka, Japan, China, and India.
In northeast, portland at its quirky best
Here’s where the city’s idiosyncratic soul finds its fullest expression, the quadrant in which both human generosity and artiste ambition take exuberant forms. Its most hallowed thoroughfare is Northeast Alberta Street.
At a store called Cord, old alarm clocks, camping lanterns, and battered can openers are arrayed like objets d’art on stark white walls. It’s hard to discern why, until owner Carey Schleicher-Haselhorst explains that her shop—named in honor of piled firewood—trades in “ranked and well-stowed” objects chosen for their simple aesthetic elegance. “Made. Found. Designed. Local. International,” reads the store’s credo.
At cozy Green Bean Books, a hub for neighborhood children, one vending machine dispenses finger puppets and another gives out fake mustaches. Meanwhile, at the grittier, dimly lit spot known as the Elixir Lab, home to rollicking live jazz, rock, and bluegrass shows, the house specialty is cool herbal drinks that improbably blend chaga and reishi mushroom juice with organic maple syrup. “We custom make a batch for each show,” says co-owner Stephen Ferruzza. “Then we let the frequency of each musical tone enter the drink.”
The biggest draw on Alberta, always, is Salt & Straw, the famed ice cream shop with an inventive, ever-changing scoop menu. Favorites include the delectable honey balsamic strawberry with cracked pepper and a spring specialty, dandelion flower sorbet. On warm nights, there is often a half-hour line snaking along the sidewalk—and it’s a party. “People hang out and meet their neighbors,” head chef Tyler Malek says. “Every single day, someone comes up to the counter and says, ‘I’ll buy the cone for the person behind me.’ The mood is happy and festive. It’s Portland.”
Photography by Robbie McClaran 
This article was first published in May 2014. Some facts may have aged gracelessly. Please call ahead to verify information.
NORTHWEST Betsy & Iya 227-5482, betsyandiya.com . Dragonfly Coffee House 224-7888, thedragonflycoffeehouse.com . Forest Park 823-4492, forestparkconservancy.org . Peculiarium 227-3164, peculiarium.com . Wild Wasabe 242-6404, wildwasabe.com .
SOUTHEAST Blythe & Bennett Records 234-6996, blytheandbennett.com . Circa 33 477-7682, circa33bar.com . Suzette 546-0892, suzettepdx.com . Tao of Tea 736-0119, taooftea.com . Twill 922-2084, twillclothing.com .