CITY GUIDE
A local’s guide to Portland, Ore.
- By JD Shadel
- Photos by Leah Nash
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Everyone seems to have a friend who moved to Oregon for a fresh start in the state’s mossy metropolis, where bikes rule the streets, cannabis dispensaries outnumber fast-food chains and chefs are akin to rock stars. Yes, it’s easy to fall for Portland, which has long touted itself as an eccentric vanguard.
Still, a full-on identity crisis is being waged between old and new, and rapid gentrification and rising costs spark heated debates as the city grows up and out. At its core, though, this big little town remains deeply proud of its instant access to lush Pacific Northwest landscapes. And with hundreds of vineyards and farms at its doorstep, plus microbreweries by the dozen, Portland certainly knows how to throw a dinner party. So wear your raincoat and come hungry.
Meet JD Shadel
JD Shadel is an independent writer and editor, who covers culture, travel, technology and LGBTQ+ life. Originally from Maryland and based in Portland, Oregon since 2013, Shadel frequently travels to report stories for national and niche media outlets. Wherever they go, they always bring a can of Old Bay Seasoning.
Want to get in touch?
Email bytheway@washpost.comRead more about JD
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Pearl District
Once a no man’s land of railroad yards and industry, the Pearl has dramatically transformed over the past two decades into a walkable district. Today, colorful trams rumble past one of the world’s largest bookstores, Powell’s City of Books, as well as converted warehouses, with cafes and breweries spilling out onto old loading docks and cobblestone streets. A couple brand-name hotels have added hundreds of beds to Portland’s most stylish neighborhood. Find this neighborhood.
Division Street
Portland’s reputation as one of the best food cities in America has a lot to do with leafy Southeast Division Street, where small-time vintners operate urban wineries and a row of chef-owned restaurants have won multiple James Beard Awards. A block or two off the mellow main drag, it’s not uncommon to see Craftsman bungalows with backyard chicken coops and residents walking cats on leashes. Unsurprisingly, there are no hotel chains here — only homey guest cottages and Airbnbs. Find this neighborhood.
Neighborhoods
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Eat
Deadstock Coffee
“Coffee should be dope” is the manifesto at Deadstock in Old Town, a popular hangout for designers and students of the nearby footwear academy. Ian Williams, a former Nike employee, runs the streetwear-themed coffee shop that doubles as a tiny shrine for sneakerheads. The mocha even gets dusted with a silhouette of classic kicks. Try the LeBronald Palmer — a blend of iced coffee, sweet tea and lemonade — along with the Trap Cake, the signature butterscotch treat home-baked by the owner’s mom.
BTW: There is no cafe menu; instead, chat with the baristas about what coffee you typically enjoy. They’ll make a drink based on your preferences.
Deadstock Coffee, 408 N.W. Couch St. Portland, Ore. 97209
Master Kong
There’s no hangover cure quite like slurping a silky bowl of congee. Master Kong’s soothing variations of the rice porridge partly explain the mid-morning lines every weekend. In a converted little house in the Jade District, sister-brother duo Amy and Kang Zhu serve a concise menu of Chinese comfort food, mostly drawn from the culinary traditions of the Tianjin and Guangdong regions. Think jianbing, a crepe-like breakfast wrap; goubuli baozi dumplings; and roujiamo “meat folders” stuffed with fatty pork. Everything arrives at your table family-style — steamy and ready to share right away.
BTW: Lines for brunch — around 11:30 a.m. on weekends — are a fact. Come a couple hours early or late to avoid the sometimes-lengthy waits.
Master Kong, 8435 S.E. Division St. Portland, Ore. 97266
Maurice
Legendary culinary editor Ruth Reichl once said she dreamed of moving to Portland simply so she could dine every day at Maurice. It’s easy to see why: Step into this luncheonette in the West End and enter an alternative universe where you wear summer whites year-round and sip rosé and eat berry tarts all afternoon. This is the French-Scandinavian fantasy domain of pastry queen Kristen Murray, who writes her menu entrees by hand, since she changes them with the whims of the season.
BTW: Maurice opens at 10 a.m. for light pastry service but does not serve the savory menu until 11 a.m.
Maurice, 921 S.W. Oak St. Portland, Ore. 97205
Nong’s Khao Man Gai
Nong Poonsukwattana has the ultimate food-cart success story: She spent most of her savings to open Nong’s Khao Man Gai in 2009, a cart where she cooked one thing: khao man gai, a Thai chicken-and-rice dish. This simple entree propelled her into the national limelight, including a winning appearance on “Chopped.” Poonsukwattana recently shuttered her original cart but has thankfully opened two brick-and-mortar counter-service restaurants, most recently downtown. And don’t worry: She’s kept the same hype-deserving item on the menu.
BTW: If it’s time for happy hour (4-6 p.m. daily), head to Nong’s eastside outpost, which pours discounted beer and wine as well as a menu of fruity cocktails.
Nong’s Khao Man Gai, 609 S.E. Ankeny St., Suite C. Portland, Ore. 97214
Kachka
Russian is the third-most-spoken language in Oregon. Thankfully, you only need to master one term at the newly expanded Kachka: zakuski, which loosely translates to “snacks to eat with vodka.” This Moscow-meets-Portland love affair is set in the Central Eastside, where Chef Bonnie Morales puts a refined spin on small plates and entrees from Russia. Morales has earned praise for dishes like Siberian pelmeni dumplings and a layered salad known as “herring under a fur coat.” The expansive list of 50-plus vodkas helps, too.
BTW: If the spirits menu seems a little intimidating, pick one of the curated flights to try the chef’s favorite vodkas, which are mostly sourced from throughout the Slavic world.
Kachka, 960 S.E. 11th Ave. Portland, Ore. 97214
Kayo’s Ramen Bar
Portland is especially gifted when it comes to ramen, with dozens of noodle shops and several outposts from celebrated Japanese chains. Kayo’s Ramen Bar commands a dedicated following in the Boise-Eliot neighborhood for its lighter, brighter, assari-style broth. The expansive menu includes a half-dozen traditional styles, but the showstoppers are Osaka native Kayoko Kaye’s fiery and inventive signature bowls. Try ordering the spicy curry or wasabi smoked salmon bowl along with the pork and kale pot stickers, and cool your tingling tongue with the matcha panna cotta for dessert.
BTW: Kayo’s stocks a notable imported sake assortment that is curated to complement the ramen menu.
Kayo’s Ramen Bar, 3808 N. Williams Ave. No. 124. Portland, Ore. 97227
Departure Restaurant + Lounge
For most of the year, there’s no avoiding the overcast skies and intermittent drizzle. But that only intensifies the local enthusiasm for summer, when the evening air tends to remain balmy and the outdoor lounge at Departure is the go-to spot for al fresco drinks. Crowning the 15th floor of the posh Nines hotel, Departure’s panoramic views are the obvious draw. The sleeper hit, however, is the pan-Asian menu, helmed by revered chef Gregory Gourdet, who grows produce for the kitchen in his rooftop garden. The indoor dining room has a garish, futuristic decor reminiscent of a nightclub — fitting since Gourdet keeps the party going until midnight on Friday and Saturday.
BTW: After 10 p.m. (11 p.m. Fridays and Saturdays), the kitchen serves a late-night menu of greatest hits.
Departure Restaurant + Lounge, 525 S.W. Morrison St. Portland, Ore. 97204
LOCALS THINK YOU SHOULD KNOW
- It’s overcast for several months out of the year. From fall through spring, come prepared for gray clouds and persistent — some say refreshing — drizzle. Thankfully, summer brings blue-sky bliss.
- Vendors from the city’s homeless population sell the award-winning Street Roots newspaper and directly receive 75 percent of the profits. Buy yourself a copy.
- Portland has a rising hip-hop scene. Pick up an alt-weekly — the Portland Mercury or Willamette Week — for a venue directory and showtimes.
Do
Alphabet District
If you have only an afternoon to spend wandering aimlessly, head to the Alphabet District, a dense checkerboard of vintage brick apartments and regal Victorians, many converted into shops and restaurants. The designated historic area, platted in the mid-19th century, centers on two avenues: Lined with twinkly lighted trees, NW 23rd has the city’s greatest concentration of boutiques. NW 21st has a village-like vibe, with cafes, a stellar bakery, karaoke clubs and dive bars. True to the neighborhood’s name, the narrow east-west streets are in alphabetical order.
BTW: NW 21st comes to life during happy hour; squeeze into M Bar for a glass of vino in what’s arguably one of the tiniest wine-and-beer lounges in the West.
From NW 17th to 24th avenues and W. Burnside to NW Marshall streets
Forest Park
Most metro areas contain pretty parks, but few have a pristine rain-forest paradise within city limits. Sprawling out over 5,156 lush acres, Forest Park ranks among the largest urban forest preserves in America. A maze of 70-plus miles of trails lures hikers, runners and equestrians. A vital habitat for many animals, including dozens of mammals and more than 100 bird species, the park makes it easy to forget that you’re still in the center of Portland.
BTW: The moderate hike up to Pittock Mansion is the most popular for its skyline views at the top. Start at Lower Macleay Park for the five-mile round-trip trek.
Lower Macleay Park, Portland, OR 97210
Portland Mercado
This hub of Latin American culture in the southeast corner of the city feels like a year-round festival, complete with a plaza lined with food carts and a casual cantina pouring regional wine, beer and sangria. Devised by the nonprofit Hacienda CDC as an incubator for Latinx-owned small businesses, Portland Mercado supports more than a dozen culinary entrepreneurs. Stop in for a survey of street foods from Mexico and Cuba to Colombia and Peru, and peruse the indoor food court, with a juice bar, Nicaraguan coffee shop, meat counter and market purveying imported and hard-to-find goods.
BTW: Check the Mercado’s calendar for seasonal events such as winter farmers markets and a makers fair marking Cinco de Mayo.
Portland Mercado, 7238 S.E. Foster Rd. Portland, Ore. 97206
House of Vintage
The caricature of Portland’s modern-day bohemia isn’t too far off the mark on Southeast Hawthorne Boulevard, which has bookstores, vintage boutiques and even the occasional sidewalk vendor selling crystals. A sprawling highlight is House of Vintage, perhaps best described as a thrift store on steroids, where wardrobe stylists for TV shows like “Portlandia” and “Grimm” have shopped for costumes and props. In the 13,000-square-foot space, more than 50 vendors line racks with styles spanning the past century, especially looks from the ’80s and ’90s.
BTW: Continue your secondhand treasure hunt at two nearby standouts: Jackpot Records and Red Light Clothing Exchange.
House of Vintage, 3315 S.E. Hawthorne Blvd. Portland, Ore. 97214
Freeland Spirits
Portland’s breweries tend to hog the booze spotlight, but its craft-spirits scene has also grown in the past decade, a trend driven by the sheer number of new cocktail bars that have cropped up. Freeland Spirits, founded by a former agricultural educator, is both the state’s first all-women-run operation and one of its most innovative: To produce its signature gin, it uses traditional methods as well as a cold distillation technique that preserves the flavors of the locally sourced botanicals.
BTW: Tours are scheduled Wednesday through Sunday at 3 p.m. The $20 fee includes a guided tasting.
Freeland Spirits, 2671 N.W. Vaughn St. Portland, Ore. 97210
Holocene
The warehouse parties never end at Holocene, a music and art club with an avant-garde bent. Inspired by the minimal techno scene in Berlin, the bi-level venue in the Central Eastside hosts an eclectic range of independent DJs and genre-blurring musicians, although most lineups tend to focus on up-and-coming sounds in electronic, R&B and hip-hop. Among concert halls in Portland, Holocene presents the most timely survey of the local scene. And with a calendar full of themed dance nights — such as the queer- and BIPOC-focused Slay — there’s something going on nearly every night of the week.
BTW: Book advance tickets online. Lines can wrap around the block for rising acts and recurring events.
Holocene, 1001 S.E. Morrison St. Portland, Ore. 97214
JD Shadel
A blue-crab-loving Marylander, JD packed a suitcase full of Old Bay Seasoning and began reporting from Portland’s many cafes in 2013. Turns out, the Pacific Northwest’s signature Dungeness crab tastes great with Old Bay, too.
Leah Nash
Leah is an editorial and commercial photographer based in Portland, Ore., and half of the photo duo NashCO Photo. She is proud to be from a place that is known for its parks, bridges, bike paths, liberal attitudes and eco-friendly vibes. Plus, you’ve got to cheer for any town that claims to have among the most coffee shops, microbreweries and strip clubs per capita in the United States.