36 Hours in Portland, Oregon

There is no place in the country better known as a bastion of good living, leisure and happy inebriation than Oregon’s largest little city, the low-lying mini-metropolis of Portland. Bisected by a river and surrounded by peaks, Portland is nothing if not a very pretty and almost preternaturally pleasant town. But much of its appeal comes from being, for better or worse, one of our national capitals of cool. The city’s sensibility — its stylized aesthetic, its thoroughly hyped food culture, its taste for irony — is celebrated, imitated and satirized. Portland is at its best, though, when you step back from its overwrought reputation and appreciate its appetite for simple pleasures: beer and bike riding, day trips to the Columbia River or Sauvie Island’s farm stands, movies in vintage theaters and cocktails in ornate lounges.
Friday
4 p.m.
Five O’Clock Somewhere
For a no-reservations-necessary seat at ultra-trendy Kachka, where kitschy “It’s a Small World” Russia meets the Pacific Northwest, arrive early for happy hour. Specials include vodkas infused with matsutake mushroom, rosemary and horseradish ($9) and Russian drinking snacks, like onion-laced Siberian dumplings of veal, pork and beef ($9). Then revisit your youth at Ground Kontrol, an arcade-bar (21-and-over after 5 p.m.), where retro games — vintage pinball machines, Street Fighter and Ms. Pac-Man — are equipped with adult beverage holders. Or take your youthful enthusiasm to Pips & Bounce, an all-ages Ping-Pong bar. Walk-in tables rent for $10 per half-hour.
7:30 p.m.
Go for the Garden
In a city noted for its casual dining culture, Ava Gene’s feels like an occasion. If possible, sit at the chef’s counter, where the kitchen provides a beautifully orchestrated show to accompany your meal. Resist the urge to order a main course and instead focus on the “Giardini” menu. Though each is described only by its eclectic ingredients (“citrus, avocado, fennel, bottarga, pistachios,” for example, or “chicories, olives, egg, Meyer lemon, anchovy”), these vegetable-centric dishes ($11 to $13 each) are exceptional.
10 p.m.
Late Night Life
On a gentrified stretch of Mississippi Avenue, Mississippi Studios offers everything from Italian indie folk to Puerto Rican garage rock and Gulf Coast soul (tickets from $5 to $20). Between sets, seek out the “secret garden” patio behind Bar Bar. For cocktails, try the Alberta Arts District’s Expatriate, a sexy little spot that feels like a cinematic take on a Thai brothel, albeit one with a big-name chef whose specialty is meat-centric, multicourse communal affairs: Naomi Pomeroy, 2014 James Beard winner for Best Chef Northwest. At Expatriate, the food is Asian-influenced “drinking snacks” ($6 to $17) and the drinks are showstoppers, like the mint green Hollygrove (Pierre Ferrand 1840 Cognac, yellow chartreuse, lemon, foreign palm sugar, fresh orgeat and blue Curaçao, $14).
Saturday
8 a.m.
Keep It Simple
Pip’s Original does two things — tiny doughnuts and chai — and does them well. Pair the simplest doughnuts ($2.95 for four) like the cinnamon sugar or raw honey and sea salt with an exotic chai (from $3.50), like the Ginger Rogers (ginger, nutmeg, Thai chile). Or, for a breakfast revelation, HA & VL serves fragrant bowls of Vietnamese noodle soup. Each day, the menu lists two varieties — Saturday is spicy beef tenderloin, sliced pork, meatloaf and vermicelli in lemongrass beef broth and “peppery pork ball” with fish balls in pork broth ($9.50) — and typically sells out by midday.
10 a.m.
Designed to Delight
Hit the West End, the downtown neighborhood best known as home to Powell’s bookstore. Flit from the funky women’s boutique Radish Underground — which focuses on independent designers, largely local, selling colorful, organic cotton underwear from New Zealand (a.k.a. “thundies”) and the like — to the nearly century-old hat shop John Helmer Haberdasher, where one can get fitted for everything from berets to straw hats. North of West sells the work (textiles, ceramics, jewelry and more) of some 30 local designers. For an immaculate meal of anisette and chocolate brioche rolls, polenta clafoutis with poached farm egg or Nora’s lefse with tarragon and grapefruit-kissed gravlax ($20 to $30 per person, including pastries, small plates, tea and wine), get to the precious and popular luncheonette Maurice the moment it opens its “le menu” service at 11 a.m.
12:30 p.m.
Keep Portland Weird
Step right up to the Freakybuttrue Peculiarium (free), an oddities museum, gallery and ice cream parlor founded in 1967, where you’ll find novelties, gag gifts, insect candies, macabre art and more. It’s creepy and strange and kids will love it. In the Sellwood neighborhood, not far from America’s oldest continually operating amusement park, another joyously offbeat option is Ping Pong’s Pint Size Puppet Museum (free). The tiny museum, workshop and puppet performance space, which opens at 2 p.m., reflect the passion of two veteran puppeteers, who live in an adjoining home.
1:30 p.m.
Bean to Bar
Woodblock Chocolate is a family-run manufactory and shop, where you can watch the chocolate-making process, gorge on samples and buy sesame, salted nib or single origin bars. Down the street, Cyril’s at Clay Pigeon is not as well-known as the rightfully famous Cheese Bar, headed by the master fromagier Steve Jones. But the unpretentious winery and cheese bar — started by a pair of Brooklyn transplants who have worked at some of New York’s most beloved cheese shops and on the wine program at the Hudson Valley restaurant Blue Hill at Stone Barns, respectively — is a no-pressure place to nibble on a cheeseboard, sample Clay Pigeon reds ($12 for a flight of three) and play pétanque, a cross between horseshoes and bocce.
4 p.m.
New Brews
In this vaunted beer city, seek out recent arrivals on the small-scale brewery scene. Ex Novo Brewing serves Moonstriker, an exceptional Baltic Porter made with local Moonstruck chocolate and habanero chiles. Base Camp Brewing has a canoe mounted on the ceiling, flights served on a “taster log” ($10 for six) and s’more kits ($3.50). The sophisticate’s choice is the Commons Brewery, expanded from a seven barrel “European-inspired” nano-brewery to a 15 barrel brewhouse with a 13-tap tasting room. The Commons’ Urban Farmhouse Ale won the Bronze Medal at the World Beer Cup in 2012.
7 p.m.
International Night
Soak up that beer with Schweinshaxen (brined and roasted pork shank with spaetzle and red cabbage, $22), or Forelle (riesling-braised trout with butternut squash, brandied cherries and hazelnuts, $16) at the new German pub Stammtisch. But if there’s one meal to have in Portland right now, it’s the multicourse, prix fixe ($70 per person), eight-seatings-per-week dinner at Lang Baan. In the back of an ordinary-looking Thai restaurant, Lang Baan offers a monthly menu of elaborate dishes — say, Ora king salmon with pomegranate, watercress, heart of palm, lemongrass, cured ikura and crispy peanut candy — that beautifully balance sweet and salty, sour and spicy and always come with a story.
9:30 p.m.
Wonderfully Retro
Line up beneath the neon lights at Laurelhurst Theater, a 1923 Art Deco movie theater that plays cult classics like “Harold and Maude,” along with blockbusters, foreign films and art house flicks. Admission is an unbeatable $4. Then cross the street and find a stool at Angel Face, where there’s a horseshoe shaped bar lit with tea lights and walls of hand-painted wallpaper.
9 a.m.
Line Up
Brunch in Portland is not so much a meal as an endurance event: The city’s beloved spots require rising early and waiting for your hung-over brethren to mosey on. At the Southern restaurant Screen Door, the fried oyster Benedict comes with Cheddar grits ($11.95) and the buttermilk-battered chicken rests on sweet potato waffles ($14.75). The wait at the nine-table Sweedeedee, where specials are written on butcher paper, can be more daunting, but the honey cake with fruit and cream ($5) alone is worth it. Mississippi Records next door has an impressive selection of R&B, soul, reggae, ska, punk and modern.
1 p.m.
Park It
Pick up a picnic basket at Woodlawn’s P’s & Q’s Market. With a $15 deposit, you’ll get a loaner basket filled with your choice of sandwich, salads and beverages. Then head to Cathedral Park on the Willamette River. Sit on the lawn or grab a picnic table beneath the majestic St. Johns Bridge. Stop into Occidental Brewing Company for crisp Cologne-style Kölsch. Afterward, sweat out your vacation decadence at Löyly, a Scandinavian-inspired communal cedar sauna and spa ($23 for two hours). Expect nudity, and call for gender-specific hours.
Lodging
For $145 per night, rent an entire tiny house — complete with kitchen, living space, bedroom and bath — at the Alberta Art District’s Caravan (5009 NE 11th Avenue; 503-288-5225; tinyhousehotel.com).
One of Portland’s oldest hotels, Sentinel (614 SW 11th Avenue; 503-224-3400; sentinelhotel.com) is the newest incarnation of former Governor Hotel, the National Historic Landmark where Gus Van Sant filmed “My Own Private Idaho.” Remodeled and reopened in 2014, the 100 guestrooms start at $249.
Distributed by The New Times Syndicate