Ring of Rum..and Fire! Brave Hale Pele's Volcano Bowl
Ring of Rum..and Fire! Brave Hale Pele's Volcano Bowl

Hale Pele: TIKI-LANDIA

Come for: The Disneyland-blitzed-on-Sailor-Jerry décor
Come back for: The Jet Pilot’s flaming, head-swirling mix of three aged rums, citrus, falernum, and a heap of cinnamon

There are tiki bars, and then there Tiki Bars. Hale Pele is the latter. Enter from a relatively dead block of NE Broadway, cross a small bridge next to a trickling waterfall, and you will find yourself within a thatched hut that feels tricked out by someone on a strong form of aboriginal acid, where psychedelic lights, bamboo, and giant Polynesian masks all clamor for attention alongside nearly 40 frothy, boozy tropical concoctions. Pretention is banished here—Hale Pele’s cheesiness is central to its charm. Spiky puffer-fish lamps overhead? Check. “Thunderstorms” blowing through the sound system on the hour? Check. A volcano that spews smoke? Triple-check! Conversations flow easily (and increasingly loudly) between strangers at neighboring tables, fueled by nibbles of addictive, sesame oil–slicked edamame and sips from the epic, rum-centric cocktail menu. The sugary classics are here (the Painkiller), but plunge deeper into the menu for a taste of the spicy side of the tropics (the Navy Grog). Just pay close attention to the menu’s “potency scale” and come with a couple of hours to spare—service tends to run on “island time,” natch. 2733 NE Broadway

The Tannery: THE SOPHISTICATED FRONTIERSMAN

Come for: Exactingly composed drinks, old (the Toronto) and new (the Namaste—with chai-infused vodka)
Come back for: Low-key, under-the-radar DJ nights on the two turntables in the back

Something funny about the Tannery: people seem to bring their parents. On a recent visit, several tables in this cozy, off-kilter-elegant shotgun shack featured 30-somethings and their forebears. Maybe Portland transplants are eager to show off a tiny gem that distills the city’s modern mood to its essence. After all, this place isn’t much more than a cinder-block shed on a once-desolate stretch of Burnside. Owner Caleb McBee refined the unpromising structure into a snug, considered
epitome of that post-Deadwood, neo-steampunk, Craftsman Industrial design aesthetic that Portland loves. Behind the bar, archival drinks like the Toronto croon dark melodies of rye and fernet, while strange new wonders take shape—the Lucille 2, for example, mingles ferocious Dutch gin, a red wine reduction, and sparkling cava. The tiny kitchen works a rich vein of Euro-Oregonian pub fare, turning out a Monte Cristo spiked with marionberries and steak frites sourced from St. Helens. It’s almost a little much, but when the needle hits some old vinyl and the booze hits the big ice cube, the Tannery serves Portland indie culture in its most refreshing form.
5425 E Burnside St

The Fireside: THE DEN OF FIRE

Come for: Backyard Grillin’ (tequila, mescal, rhubarb amaro, lemon, orange bitters)
Come back for: The opportunity to drink that cocktail (and many more) beside one of two fireplaces

We lamented the demise of the iconic Music Millennium on Northwest 23rd Avenue as much as anyone. But after six long years of vacancy, what’s risen from its ashes is a small triumph: an enticingly homey neighborhood joint with a fireplace-to-space ratio that we heartily approve. Yes, the Fireside is inspired by (you guessed it!) all things fire, from its ax door handle to its floor-to-ceiling smokestack fireplace. The outdoorsy food menu includes a hearty elk chili and plenty of grilled things, from flatbread pizza to lettuces and brick chicken, while a wallet-friendly spread of cocktails (just $6 apiece during happy hour) offers fiery, smoky mescal- and scotch-fueled concoctions. Partitioned nooks and booths, all bedecked in buttery leather and fiercely grained wood, give you plenty of options for tucking into the scene: hole up in a dark booth with a group; sidle up to the bar in a tufted, swiveling seat; ogle Nob Hill shoppers at a window seat beside the open fire pit; or kick back with strangers at the front fireplace. Bonus challenge: see if you can find the “speakeasy bathroom.” 801 NW 23rd Ave

Free House: THE HOLE-IN-THE-WALL

Come for: Brawny house creations like the Maine Coon (rye whiskey, sweet vermouth, maple syrup, and salt) or Calcutta (black rum, lime, Campari, bitters, sparkling cider)
Come back for: The pˆaté bahn mi—a high draft choice in Portland’s bar-bites fantasy league

If you want to see the humble neighborhood tavern raised to an art form, come here. Crammed almost invisibly between a tattoo shop and an Irish pub, Free House feels like an off-the-radar discovery every time you walk in. Amid clean-lined but cozy décor, a connection to artisan meat empire Olympic Provisions (the two share a co-owner) elevates a tightly edited menu of charcuterie, snacks, and “sandos” to heights few publicans would dream of. Behind the bar, a cheeky sense of invention reigns: an old stalwart of the house list, the Dagobah System combines a geeky reference to Star Wars, evocative sense memories of Coca-Cola, and the best cough syrup flavor imaginable. On the other hand, the Blazers are on and the laid-back but all-pro barkeeps will crack you a cheap Old German if that’s more your speed. If all holes-in-the-wall were like this, there would be more holes in more walls. For now, let us revel in Free House. 1325 NE Fremont St

Higgins Bar: THE URBAN IDLER

Come for: A beautiful manhattan (that’s right, it’s just a manhattan)
Come back for: The Higgins Burger—the one that inspired all the other fancy burgers in town

Every city needs places like this, and Portland has too few. There’s a door off a downtown side street. (It’s connected to a white-tablecloth restaurant—Greg Higgins’s pioneering farm-to-table stronghold—but that’s not what you’re here for, not tonight.) Inside, the walls are wood, the ceiling pressed tin, the décor unchanged for at least 10 years. The staff wear ties. The room is buzzing, but not beholden to some concept of cool or any particular subculture—anyone could be anyone. You’re there before a show, or after work, or neither. The house classics on the cocktail list date back at least 31 years. The person making your drink did not invent it, s/he just knows how to make it right. The guy next to you orders a fresh Stoli on ice by pointing wordlessly at his empty glass. You drink your martini, or your sazerac, or your manhattan, and you remember what a city bar is actually for: a neutral, civilized, well-tended place to savor that little piece of time between one thing and the next. Higgins masters the almost-lost art of being that place. 1239 SW Broadway

Red Letter: Spot-on pours at Richmond Bar
Red Letter: Spot-on pours at Richmond Bar

The Richmond Bar: THE CLASSY NEW NEIGHBOR

Come for: A tumbler of sassafras-spiked mescal and some fetching wallpaper 
Come back for: Epic white cheddar–and–caramelized onion mac and cheese

Restaurateur Nate Tildenhas made his mark in town by knowing exactly what Portlanders crave, from cured meats (Olympic Provisions) to Jeffrey Morgenthaler (Clyde Common). With Richmond Bar, he bestows upon Southeast Portland a compact greatest-hits collection in the former Matchbox Lounge’s Lilliputian space. Gangs of clever women and bearded men crowd the black-leather banquettes, while neighbors meet over pints of 10 Barrel and a righteous chopped salad sprinkled with meaty OP goods at a tall communal table that commands the center of the room. Co-owner and Clyde Common alum Nick Gusikoff brings a smart parade of well-balanced cocktails to the convivial party that skip from light and fizzy (the Clear Creek pear brandy and Chartreuse-laced Park Life) to silky-smooth (bourbon-backed Honey Suckle). Our favorite new SE Division Street resident? The Sassafras. With a smoky mescal burn and a bittersweet, brawny one-two punch of cynar and root-beery liquor, it’s sexier than most men in this town. 3203 SE Division St