Old Portland is alive and well in this corner of downtown Portland—and that includes a 50-plus-year-old strip club, stiff martinis, and one sprawling book mecca. Sure, the city’s outlying neighborhoods have Paul Bunyan statues and Japanese gardens, but the West End boasts a handful of the most iconic Portland spots of all. 

Powell’s Books

A veritable Portland landmark, Powell’s City of Books is known far and wide as the largest independent new and used bookstore in the nation. It takes up a full city block and is four stories tall, comprising approximately 1.6 acres of retail floor space. It’s basically the city’s wood-pulpy, secular, color-coded church—flocks of faithful communing in their chosen areas, from the sci-fi and fantasy-packed Gold Room and Blue Room fiction and poetry sprawl to the Purple Room’s cerebral histories and philosophies and Pearl Room’s art bounty. Amen. 

Benson Hotel Palm Court

Should Portland’s casual airs make you long for a touch of social grace, slip into the lobby of the Benson Hotel and head straight to the bar. If the Palm Court’s 30-foot-tall molded ceilings and multistory chandelier dripping with crystal don’t instantly elevate your station, then give the red-and-gold leopard-spotted banquette a little stroke. Call over the most attractive bartender, the one with pomade in his hair, and order a manhattan. Have two while pondering the huge stone urn in the corner and the wall of bottles behind the bar, or that ritzy-looking man with the tan suitcase in the corner. At the Benson, opulence, thank heaven, is not a thing of the past. 

Cacao

A sweet example of Portland’s yen for loving on a product until it forms a cult, Cacao stocks otherworldly chocolate offerings, the kind that, once you’ve tasted them, there’s no going back to those chalky bars that lurk near checkout counters. The expertly curated spot offers a mix of decadent treats culled worldwide. The menu includes a dizzying array of bars and seasonal handmade confections, from fig-and-fennel chocolates to sea salt–tinged caramels. Behind the counter, three constantly churning machines keep Cacao’s heady drinking chocolate in a warm, liquid state. And because the very notion of a “Parmigiano-Reggiano chocolate” piques curiosity, sampling is encouraged. 

Mary’s Club

Back in 1965, owner Roy Keller turned Mary’s Club topless, making it the first Portland skin joint of its kind. More than a half-century later, it’s still there. And it still feels like Old Portland: ladies choose their own songs from the jukebox on the postage stamp–size stage, bartenders pour stiff well drinks, and a tide of tired regulars, tourists, and gawkers washes in and out of its cramped seating area—the family operation still run by Keller’s daughter, granddaughters, and a great-granddaughter. Sure, plenty of patrons come for the flesh parade, but many more come to ogle Portland history, from the stage where Courtney Love and Viva Las Vegas once stripped to La Monte Montyne’s fascinating black-lit mural of paradise islands and merchant seamen that stretches across the back wall. Pink Martini bandleader Thomas Lauderdale hails it as a local landmark on par with Darcelle’s: “[Visiting Mary’s] is a rite of passage in Portland urban life,” he says. “I take all my out-of-town friends here ... especially the ones from New York.”

Rich’s Cigar Store & Magazines

One of the West Coast’s best selections of magazines (plus tobacco and pipes, if you’re into that) hides behind this relatively nondescript, beige-green façade. Stock up on Le Monde Diplomatique, Smith Journal, Der Spiegel, FourFourTwo, and any number of ultra-obscure fashion mags, ask for some U.K. Dunhill pipe tobacco, and declare temporary independence from the tyranny of digital media. It’s a treasure.*

* “If it ever closes I will burn Portland to the ground,” says Portland Monthly editor in chief Zach Dundas.