There are many valid reasons to visit Oregon, but this is not an account of the piney coast, not a guide to connecting to the natural world. This is a weekend bender for advanced deviants, an urban adventure demanding total allegiance to indulgence. To partake of Portland’s quirky traditions, to imbibe by the customs of its citizens, to flirt with excess without becoming excessive: This is the oath by which we stand, until we can stand no more.
But first, we must orient ourselves. PDX splits neatly into four quadrants, using the Willamette River and Burnside Bridge as its vertical and horizontal axes, respectively. The southwestern quarter holds downtown— and your home base. The Ace Hotel introduces but one problem: You won’t want to leave its cool comfort. The boutique lodgings recall childhood fort dreams materialized and matured, offering luxury in beautifully simple details: ample natural woods, pillows that swallow your head, hooded terrycloth robes and, for the ladies or forward-thinking men, a black washcloth to clean those heavily lined eyes. Daily European-style breakfasts tempt with house-pickled vegetables, cured meats and cheeses, fluffy breads and spreads, shards of bitter dark chocolate and French-pressed coffee from revered local roaster Stumptown.
You might people-watch in the Ace’s inviting communal workspaces, but don’t linger too long. It’s time for a pre-binge cleanse at Prasad, three blocks from base camp—for the surest palate is a clean one. At first glance, it looks like an unassuming cafe, but the medicinal properties therein cannot be underestimated. Order a coconut cider, a frothy, spiced concoction of fresh apple-ginger juice steamed with coconut milk that both warms and tempers. Then raise your fork to the chipotle chili bowl, crisp with a quinoa bite that cuts smoky chili, greens and avocado smothered in peppery cream sauces. Cap it with your first shot of the trip: two ounces of ginger-lemon juice spiked with cayenne and echinacea, chased with an apple slice.
Use the early afternoon to get a lay of the land and its artisanal craftings. Across from the Ace, the Union Way hallway leads to Danner, Portland’s premier purveyor of hide. The rugged footwear shop even smells like the great outdoors, thanks to Danner’s living wall, stacked floor to ceiling with succulents and grass. You might recognize the boots on display as those worn by Reese Witherspoon in her recent turn in Wild, based on the memoir by Portland local Cheryl Strayed, who trekked 1,100 miles along the Pacific Crest Trail.
Your trek to the Dump Truck food cart is only a few blocks. Stock up on chewy, delicate dumplings with unique fillings and sauces, all served over a tangy slaw, and carry them to Blue Star, where it takes 18 hours to turn brioche dough into donuts with high-brow twists, like a classic glaze spiked with horchata. Bring your goods around the corner to Bailey’s Taproom and spread them across the bar while sipping your choice of more than 20 craft brews. The options rotate frequently but heavily feature Oregon taps (the Boneyard IPA is a must if available). Bailey’s also offers 4- to 10-ounce pours of everything for around $3, which means you can sample all the local purveyors—or fall off your stool trying.
Take a beer nap back at the Ace and freshen up before heading out for the night. To lay a solid base buzz, visit the Multnomah Whisk(e)y Library and sit among more than 1,600 brown spirits, which line the ceiling-high shelves so vastly that bartenders use a classic wheel ladder to retrieve the ordered bottles. There’s no pressure to know your browns, so unless you do, don’t mess with the book list—opt instead for the Old-Fashioned. Anyone can make the classic cocktail, but only a master can make it worth ordering at a bar known for its whiskey selection. Order at least two in preparation for your next destination.
Strip clubs—dozens of them—dot the streets of Portland, which boasts more skin parlors per capita than any other U.S. city. But these aren’t all just divey, dark holes. In Portland’s outskirts, there’s the all-vegan, all-nude Casa Diablo, where they serve surprisingly enjoyable plant-based grub—so long as you can get past eating a burrito just feet away from wobbly bits of bare flesh and the occasional glimmer of a
sparkle-ended butt plug. The downside: The ATM and bar distribute only $2 bills, and recent allegations suggest that the ownership may hold animals in higher regard than its dancers. Closer to downtown, options for a tamer experience abound, including Portland’s oldest topless joint, Mary’s Club, where rocker Courtney Love highlights the alumni list.
Wakey, wakey, hungover and cranky! But not for long. Skip the Ace breakfast today in favor of Juniors, a locals’ secret just across the river. Here, it’s all about the strong coffee (keep it comin’!) and the migas: Heat from jalapenos, green chilies and chorizo stops your hangover cold, while tortilla chips soak up scrambled eggs or savory tofu, zesty salsa, creamy cotija and sour cream. Add spinach to round out the dish with a velvety bite, and a pint-sized bloody mary to lull you into a relaxed stupor all the way to the airport.
-Skip the taxis—get unlimited rides for $5 a day on PDX’s public transportation, with a rail that goes from the airport and throughout the city.
-Visit Powell’s City of Books, the world’s largest new-and-used bookstore, which takes up a city block and offers a map for navigation.
Ace Hotel 1022 SW Stark St., Portland, Oregon (503-228-2277) acehotel.com/Portland
Bailey’s Taproom 213 SW Broadway (503-295-1004) baileystaproom.com
Blue Star Donuts 1237 SW Washington St. (503-265-8410) bluestardonuts.com
Casa Diablo 2839 NW Saint Helens Road (503-222-6600) casadiablo.org
Danner 1022 W Burnside St. (503-262-0331) danner.com
The Dump Truck SW Alder St. between 10th and 11th, dumptruckpdx.com
Juniors Cafe 1742 SE 12th Ave. (503-467-4971) juniorscafepdx.com
Mary’s Club 129 SW Broadway (503-227-3023) marysclub.com
Powell’s City of Books 1005 W Burnside St. (503-228-4651) powells.com
Prasad 925 NW Davis St. (503-224-3993) prasadcuisine.com