There’s no doubt about it. Portland is a drinking town.

In a city where wet-brain dives and high-end cocktail bars proliferate in equal abundance, the options are myriad. You can have it all here: Jello shots or locally distilled brandy. A glass of smoked ice or a basket of deep-fried clam strips. A meat-market or a bar with its own butcher case.

With so many places to choose from, how do you narrow it down? How do you separate the dives from the hidden gems, the trendy from the transcendent?

In the interest of saving you time and effort (that you could be putting into drinking), we had a great idea: Why not ask the experts themselves what makes a great watering hole?

We asked some of Portland’s best-known bartenders to share what they look for when they go out for a drink and give us the low-down on some truly great bars. In the interest of quality journalism, we visited a handful of their favorite spots to get the scoop on the places where service industry insiders go to drink.


“Stiff, Cheap, Mellow.”

Bartender Kara Yoshida says, “service industry people appreciate the fact that we get to know them and learn their drink orders." Photo: Natalie St John

Partially obscured by the large sign of its rowdier neighbor, Scooter’s, Cassidy’s Restaurant and Bar has been quietly holding its own on the corner of SW 13th and Washington since Mork & Mindy was on prime time.

The bar tends to fill up after downtown restaurants close, when authorities like Clyde Common bar manager Jeffrey Morganthaler head over to take advantage of their excellent and very affordable late-night happy hour menu.

An anonymous line cook enjoying an after-work drink summarized the appeal of Cassidy’s thusly: “Stiff, cheap, mellow.”

In addition to serving great food in a no-fuss setting, Cassidy’s has earned a reputation for catering to those who work late. The staffs from Jake’s, Pazzo, Teardrop Lounge and the Driftwood Room are frequent customers.

According to Cassidy’s bartender Kara Yoshida, “service industry people appreciate the fact that we get to know them and learn their drink orders. And if someone came in at 2:25, and they could get it done by 2:30, we’d serve them. Last call is at 2:29.”

“The bartenders are fast and friendly,” says Morganthaler. “They always hold down a solid crowd, pour a stiff shot and a full pint, and know what they're doing behind the stick.”

Cassidy’s Restaurant and Bar, 1331 SW Washington St., 503.223.0054


“She and Her Staff Take the Time to Get to Know You.”

Bar owner Melanie Brandy keeps a well-stocked liquor shelf, and enough PBR to keep the hipsters happy too.
Bar owner Melanie Brandy keeps a well-stocked liquor shelf, and enough PBR to keep the hipsters happy, too. Photo: Natalie St John

Justin Atkins, the owner-bartender of Vintage Cocktail Lounge, extols the virtues of supporting bartender-owned bars.

“That's when you know the person behind the stick really does care,” he explains. “I just can't support places that employ geeked-out cocktail nerds that spend their whole shift in the corner playing mad scientist. They make impeccable cocktails, but can't come say ‘hi’ and have a conversation.”

Atkins has found the perfect antidote to sterile cocktail nerdistry in his former employee Melanie Brandy’s new bar, The Foggy Notion. After setting out on her own last year, Brandy bought and remodeled the former Blue Parrot on Lombard. “I told Justin I couldn’t do it. I was only on chapter six of How to Open a Bar for Dummies!” she laughs.

The Foggy Notion is a unicorn of a bar—that rare place where true cocktail aficionados can find all of the top-shelf liquor and perfectly mixed drinks they crave in a completely pretension-free atmosphere. Inside the bar, patrons will find a row of pinball machines, a stage that regularly hosts punk and rock bands, an affordable menu of made-to order food with vegan options, and a welcoming, laid-back staff.

“Melanie Brandy has the personality that keeps me and others coming back,” says Atkins. “So that's why I love her place.”

The Foggy Notion, 3416 N Lombard St., 503.240.0249


“He Makes a Fine Cocktail.”

Alex Manning mixes prohibition-era cocktail behind the nickey-plated bar inside St. Jack
Alex Manning mixes prohibition-era cocktail behind the nickel-plated
bar inside St. Jack. Photo: Natalie St John

“The food is cheap, and the beer is cold. Those are our only requirements,” says Tommy Klus, the bartender at Kask, who has also mixed drinks at Bluehour, Teardrop and Central.

But when the urge hits for an expertly crafted cocktail, he might head over to St. Jack, where bar manager Kyle Webster has created a menu of thoughtfully updated takes on classic cocktails.

“When I make a drink, my rule of thumb is, ‘would you order three of them?’” explains Webster. This emphasis on quality and balance is evidenced in cocktails such as the delicious ‘last word,’ a formerly sugary Prohibition-era gin drink altered slightly for the more discerning palates of modern-day drinkers.

Webster and the other staff of St. Jack have put apparent effort into creating an atmosphere of “artful clutter” that is both romantic and welcoming, and a cocktail menu that is both food-friendly and accessible. Says Webster, “I want every drink to be accessible to a 22 year-old sorority girl or a 40 year-old cocktail blogger.”

St. Jack, 2039 SE Clinton St., 503.360.1281

“I Want to Be Able to Sit and Talk.”

Secret Society bartender Chelsea McAlister mixes up a round of Moscow Mules
Secret Society bartender Chelsea McAlister mixes up a
round of Moscow mules. Photo: Natalie St John

In nearly every conversation, the bartenders with whom we spoke emphasized their love for low-key bars that make it possible to relax and talk. When Mike Robertson, bartender at the Driftwood Room, is out for a drink, he likes Secret Society for just this reason.

“At Secret Society, they make a well-crafted cocktail, and Jordan [one of Secret’s friendly bartenders] is always ready with the right suggestion and a willing ear. We like the nice, relaxed vibe of the place and the small, intimate room,” he says.

The appropriately-named Secret Society occupies a hidden spot at the top of a flight of stairs above Toro Bravo, in the former meeting hall of the Woodmen of the World. On nights when local musicians perform in a corner of the wood-paneled main room, the tiny bar has the feeling of a 1920s speakeasy. When the bands aren’t there, it’s the perfect place to choose from the broad menu of classic cocktails, order a basket of fresh, hot popcorn, and talk late into the night.

The Secret Society, 116 NE Russell St., 503.493.3600

“It Just Feels the Way a Bar Should Feel.”

Patrons at Leipzig Tavern inside Gino's Restaurant can enjoy classic cocktails and italian food at the vintage wooden bar.
Patrons at Leipzig Tavern inside Gino's Restaurant can enjoy classic cocktails and Italian food at the vintage wooden bar. Photo: Natalie St John

The Leipzig Tavern in Sellwood wears the mantle of history well. It’s the kind of place where your grandfather might have gone to drink, in a good way.

Back when Sellwood was a boomtown, the bar, which has operated since the 1930s, used to cater to fishermen who would clean their catch in the back. Leipzig was incorporated into Gino’s about fifteen years ago, with the caveat that the original sign remain in place.

Contemporary drinkers will appreciate the beautiful salvaged-wood bar, excellent wine list, and friendly, knowledgeable staff that specializes in making straightforward versions of classic cocktails, and may find the smell of Gino’s steamed mussels as intoxicating as the drinks themselves.

In addition to attracting a neighborhood clientele, Leipzig is a favorite of local service industry workers and is patronized by staff from the Secret Society, Laurelhurst Market, Stumptown, and Nostrana, among others. Mike Sellers, bartender of Secret Society, loves Leipzig for its classic ambience. “It just feels the way a bar should feel.”

Leipzig Tavern, 8051 SE 13th Ave., 503.233.4613