How to Visit Portland Like a Celebrity
No place can beat L.A. or New York for celebrity sightings (except maybe Indio during Coachella or Park City during Sundance). But Portland has more than its fair share. Here, the six spots where you can follow in the footsteps of the city's most famous residents, past and present.
1. Stay at the Sentinel Hotel
Director Gus Van Sant filmed three movies in and around Portland. Portions of one of them, My Own Private Idaho, were shot in a then-vacant building that once housed the Seward Hotel, which later became the Governor Hotel and then a carpet store. Reopened as the Sentinel in 2012, the 100-room National Historic Landmark now has a rooftop hive and pints of Salt & Straw on the room service menu. For another hit of Van Sant, scope out the Lovejoy Columns, which make an appearance in Drugstore Cowboy.
2. Drink at Dot's Cafe
Good Will Hunting was nominated for nine Academy Awards, including one for best song, by Elliot Smith. Before he died in 2003, Smith lived much of his life in Portland, and one of his favorite haunts was Dot's, a divey local institution with $2 beers on tap and velvet paintings on the walls. The original owners sold it in 2012, but it reopened largely intact that same year. Still on the menu: jalapeño cheese fries.
3. Eat at Oba Restaurant
Oba was the setting for one of the best sketches from Season 3 of Portlandia. (Refresher: the Emmy-nominated show stars and was co-created by local Carrie Brownstein, who has a small role in Carol). In it, an epic birthday party culminates with tapas at this Pearl District hotspot. In keeping with Portland's obliging vibe, the Nuevo Latino menu has gluten- and dairy-free subcategories.
4. Linger at Broadway Books
Powell's is the city's most famous independent bookstore, but its size can be overwhelming. This smaller-scale indie sells signed copies of Portland writer Cheryl Strayed's Wild, the book that became a Reese Witherspoon movie, as well as Strayed's newest, Brave Enough. They also carry staff picks, host a monthly reading series—and are conveniently located across the street from the nearly 100-year-old Helen Bernhard Bakery, another Strayed fave.
5. See a Show at the Aladdin Theater
John Waters of Hairspray fame has performed his annual X-rated Christmas monologue at this onetime vaudeville house. Comedians David Cross (last seen wearing silk pajamas in Pitch Perfect 2) and Adam Sandler have done standup here. Some of the players behind your favorite soundtracks have rocked out on the stage. On any given month, you can see folk singers, cellists—even a live podcast taping.
6. Shop at Wildfang
Portland isn't known for its fashion scene. But Ellen Page, Kata Mara (look for her in The Martian), and Evan Rachel Wood are all fans of this boutique, which has a tomboy aesthetic that translates into suits, blazers, and—of course, because it's Portland—flannel shirts. Pick up exclusives from the eponymous line as well as Herschel, Redwing, and Native Youth at either the original Fort Wildfang location in the Southeast neighborhood or the newest one in Southwest.