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8031 NW Skyline Blvd., 503-286-4788, skytav.com. Noon-midnight daily.
Established: 1923
Luckily, nothing much has changed since this watering hole high atop Forest Park, amid hardworking scumbags and the richest people in Portland, won WW's Bar of the Year in 2016. The rickety-looking tavern high above the city is still one of the best places to escape for a quick scenic drive and a beer with a side of fresh air. The expansive, parklike patio can't be beat on a sunny day, especially if you're into activities like horseshoes, pingpong or day drinking and smoking cigarettes. Bring your own dogs or burgers, and you can cook them on the backyard grill like it's a '50s cookout.
But if you're some sort of heathen who doesn't like drinking beers outside, you can sit in the cozy, cabinlike bar and look out the window while listening to the die-hard locals complain about the death of Old Portland. The menu offers a few sandwiches and snacks and there's no hard liquor—probably a good idea since you'll have to get down the mountain at some point—but the beer list has a good mix of styles from local breweries, including Rosenstadt alt and Breakside Wanderlust IPA. If you're feelin' really outdoorsy, plan a hike that ends at the bar. Just make sure you plan ahead how to get back home.
Bar story: There's some interesting stuff going on around the patio, and I'm not talking about the people. It's called art, and it's one of the reasons the Skyline still exists. The bar helps support owner Scott Becker's nonprofit, Black Dog Art Ensemble, a project that he created to help explore environment and social issues. Have questions about the installations? The details are next to the back door.
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