When Kyle Linden Webster  is not fashioning Dead Romans and Kangaroos—two of his signature cocktails at Expatriate, the Northeast Portland boîte he co-owns with wife Naomi Pomeroy—he spends some of his downtime at two of the city’s best-loved wine bars. Why? “I think the wine service in town is better than the cocktail service these days,” he says.

Webster name-checks NE Alberta Street basement gem Les Caves, “a bar that doesn’t try to be anything other than itself.” It’s a place he dubs “completely idiosyncratic,” its subterranean locale lending a “secret hideaway” vibe to a personal, curated experience.

Then there’s Davenport, the East Burnside food-nerd mecca from chef Kevin Gibson and wine guru Kurt Heilemann. “I think it’s the best restaurant in Portland, and I’ve thought that for a long time,” says Webster. But it’s the wine program that has Webster waxing lyrical. “Kurt is a completely, beautifully insane man,” he says matter-of-factly. “If you go into Davenport and you look behind the bar, it looks like a bomb went off. There are bottles everywhere in no discernable arrangement—boxes and crates. You feel like you’ve wandered in while someone’s in the midst of spring cleaning, but he’s always able to pull out the
perfect thing.”

An avid record collector and DJ, Webster often forages for vinyl at NE Alberta’s Musique Plastique, or can be found walking the record stalls at Hollywood’s Antique Alley and Montavilla’s Monticello Antiques. But his go-to spot? “No. 1, always and forever, is Beacon Sound on Mississippi,” he says. “It’s not a huge shop, but it has a point of view. Beacon Sound is one person’s taste in a room, and Andrew [Neerman, proprietor] has incredible taste.”

Webster, 37, says his record shopping habits have changed since his more leisurely 20s. “I don’t have time to dig and find everything in the way that youth allows for, so it’s fantastic to be able to walk in and toss out a style and say, ‘What am I missing right now?’ You walk out with a beautiful pile of brand-new sounds.”