You have one week before Portland self-destructs. Time’s ticking so here’s a week’s worth of venues to check out and check off your bucket list. (Plus a bonus option for Sunday if you're seeking something that's not entirely musical but nonetheless devilish.)
Monday at Al's Den
This intimate, underground lair doesn’t just feel like a speakeasy, it was the actual turf of Portland’s gambling kingpin Al Winter in the 1940s. Today’s scene features free music every night starting at 7pm—that’s stripped-down, week-long residencies with local and national talent, both known for inviting a selection of new special guests each night along the way. With a typical McMenamins’ flair for interior decoration, concert posters even cover the bathroom walls and, if you’re of a certain gender, don’t miss the massive, turn-of-the-century porcelain urinals.
Check these off your list:
▶ Enter the subterranean digs through the triangular Ringlers Annex entrance on West Burnside.
▶ Belly up to the bar and order a Big Al’s Old Fashioned (made with Edgefield’s single malt Hogshead Whiskey, homemade vanilla-bean syrup and cherry bark-vanilla bitters, served over one large ice cube) and anything off the menu of the Zeus Café upstairs before making your way into the dim, cozy confines of the den.
▶ Hitting a show at the Crystal Ballroom later? It’s just a block away and your receipt earns you early entry before the doors open.
▶ Feeling tipsy post show? Get a room in the Crystal Hotel back where you started—which'll also gain you access to the adjacent soaking pool.
Tuesday at Doug Fir Lounge
A perennial favorite with musicians and fans, this log cabin bunker with an exceptionally touted sound system packs a punch of up-and-comers alongside revered acts—from locals to international legends—almost every night of the week. The minimalist but efficient downstairs venue is complemented by an additional bar and restaurant upstairs that aesthetically straddle the line between Twin Peaks and a cosmopolitan truck stop diner, full of Northwest woodwork and mid-century modern design.
Check these off your list:
▶ Once you’re in, the entire space is your playground with bars upstairs and down and plenty of nooks and crannies indoors and out, including a picnic-tabled patio with firepit.
▶ Order a drink at the first bar you bump into, but if you’re looking for something you can’t get anywhere else, try the Old Forester (a single-barrel bourbon that the DF hand-picked at the distillery in Kentucky) on the rocks with a Doug Fir Logger beer back, which was created exclusively for the venue by Breakside Brewery.
▶ Gotta go? If you use the venue’s bathroom, you may very well bump into the night’s headliner since there’s no can backstage. But if that’s crowded and you decide to hop upstairs, don’t get turned around in the cramped quarters of the mirror-filled, funhouse-esque space. Then again, don’t be too embarrassed if you do because the bar staff is already familiar with the “spectacular thuds” that emanate from within.
▶ Show’s over and you’re starving? The restaurant stays open late (and opens early—it’s actually open 20 hours a day) so grab a Fir Burger with candied bacon. And order your fries extra crispy.
Wednesday at Mississippi Studios
From a Baptist church to a recording studio to a live music venue created for musicians by musicians, the lovingly crafted, sonically superior, intimate room recently saw a remodel that efficiently reconfigured the in-venue bar and streamlined the space. Located in the heart of Historic Mississippi Avenue’s commercial corridor, the venue hosts two- and three-band bills just about every night, each backed by illuminated bass drums emblazoned with the marks of other local, musician-owned boutiques like instrument specialists Revival Drum Shop and Black Book Guitars.
Check these off your list:
▶ Chairs are only available on high so arrive early if you want the bird’s-eye view from the seated balcony.
▶ But if you show really early, plunk down in the adjoining Bar Bar or on its massive patio and start with a $5 daytime drink special—margarita or Bloody Mary. Although that ends at 4pm, it's precisely when happy hour starts.
▶ Seeing as it’s a burger lounge, the rotating Burger of the Month is a requisite. Pair with fries or onion rings, but if you insist, you could get something healthy on the side like a kale salad.
▶ Take your drink inside the venue, bask in the dim glow of the orbed chandeliers between acts, and when all the dancing is done, head back to the patio and settle in next to an open flame or find an isolated corner in the secret garden.
Thursday Evening at Mississippi Pizza
Whether you’re seeking a slice or a full pie, let it be known that Mississippi Pizza is not a parlor. There is the typical dining area with the glass case displaying cheesy concoctions that you’d find in any pizza place, but then there’s a door that leads into a separate, spacious music venue with a back-corner bar, the Atlantis Lounge. The calendar’s always full of local talent, and early shows are donation only while later 21-and-over concerts—featuring everything from three-band bills of indie rockers to hip-hop to plenty of bluegrass, blues, swing, jazz and singer-songwriters—often have a cover of no more than $5-10. Plus, international flavors are represented by Balkan and Middle Eastern music as well as two nights a month of salsa dancing with a live band.
Check these off your list:
▶ Most nights see multiple acts (or events like Bingo and Bourbon with Brian Perez on Mondays, Baby Ketten Karaoke every Tuesday, trivia, or DJ nights) take the venue’s intimate stage and evenings often start with family-friendly performances by the likes of kids' music mainstays Red Yarn (Thursdays), Mr. Ben (Tuesdays) and others.
▶ Parents or those coming for later shows can order fresh-squeezed juice cocktails (like the ever-popular margarita) or glasses of wine and pints of beer from one of the eight rotating taps.
▶ Showed up hungry or worked up an appetite? The pizza is worth your time, and it comes sauced with reds, whites or pestos and topped with countless options that are meat- and veggie-filled as well as vegan and gluten-free
Thursday Night at The Secret Society [CLOSED]
If it's Thursday night, head to Jumptown—that’s hot jazz swing dancing in Portland’s most secretive ballroom with a storied history. Built by the Woodmen of the World in 1907 and home to Portland's African-American Freemasons for nearly 50 years, today the ballroom hosts a proudly eclectic lineup of intimate live music and events. Decked out in velvety blood reds and dark wood, the former members-only fraternal organization now features a female-only women’s lounge as the entry to the washroom and a full-service recording studio directly below the ballroom, which is even equipped to capture live performances happening upstairs.
Check these off your list:
▶ As you head up the stairs to the second-story suite, check out the black-and-white photos remembering the space’s former inhabitants.
▶ Poke your head into the snug, street-facing, lumberjack-walled lounge and order one of the many craft cocktails that makes this place a destination. Moscow Mules are of course served in coveted copper cups, Manhattans and Old Fashioneds are ever-popular, and it’s one of the only places in town to offer a full range of absinthe served in traditional French fountains.
▶ Snacks or dessert—why not both? There’s certainly a full menu but finger foods are more fun: Get popped-to-order popcorn with olive oil, black pepper and parmesan, or let your eyes stray to the after-dinner offerings and try something akin to a vintage Jell-O shot—cocktail jellies in classic varieties like Manhattan, Negroni or Kübler Absinthe, each paired with dessert sauces.
Friday at Holocene
Yet another mid-sized Portland venue known for booking an artistically diverse offering, this converted warehouse with sweeping white walls and 25-foot ceilings definitely caters to a dancier demographic with regular DJ nights every weekend supplemented by indie rock, electronic music, art installations, storytelling, film screenings, modern dance, and other events throughout the week.
Check these off your list:
▶ If you show early before the crowds and noise, there's plenty of loungeable space for you to catch up with friends and make a memento in the photo booth before things get hazy.
▶ Need a pick-me-up to make it through the night? Order a No Naps: hot Stumptown coffee, Lemon Hart 151 rum, Averna liqueur and soft cream with an orange twist. Plus, load up on European-sounding "comestibles," which taste as good as they sound especially if famished by dance.
▶ Can’t stand the heat? If the bodies have turned the space into a sweatbox, step outside for a breath of fresh air—just be careful not to be lured away from your party inside and across the street by the glowing marquee of an equally beloved institution: Sassy’s strip club.
Saturday at Star Theater
A historic silent film house turned burlesque theater that’s been elegantly remodeled (yet still reportedly haunted by the ghosts of pasties past), the Star Theater was reopened in 2011 in time for its 100th birthday. With its booths, bar areas and an isolated balcony, the room feels strangely put together but has a feng shui that works and sounds great—plus offers all-ages shows to boot.
Check these off your list:
▶ Arrive early so you can explore the place uninhibitedly or claim the booth beside the soundboard.
▶ Go for the gyro: Stuffed with lamb, feta and tzatziki sauce (and splashed with sriracha if you want), the Mediterranean cuisine comes courtesy of the revered food cart Zaalook.
▶ Crowded inside? Step outside, enjoy the sweeping patio, and huddle around the firepit if you’re feeling frigid.
Sunday at Rontoms
Devout Portland music scenesters and aficionados flock to their indoor-outdoor (depending on the season) house of worship for impeccably curated, free Sunday Sessions in SE Portland. The man behind the scenes is Theo Craig, the sole booker responsible for bringing all sorts of rising local and touring talent to “the city's biggest intimate music venue—Portland music is made here,” he says.
Check these off your list:
▶ If it’s wintery, there’s plenty of space on the palatial patio—room enough for Ping-Pong—but if it’s summery, the patio’ll be packed.
▶ So what does the talent buyer drink? Kamadeva's Bow: Laird's Applejack brandy, Bärenjäger, fresh lemon and orange, hot water.
▶ If your tummy starts to rumble, power through a burger or “go for that beet salad if you're ‘trying to be good,’” Craig suggests.
▶ A word from the wise: “The bartenders can totally hear how that Tinder first date is going and they know how much you tip. Keep that in mind and tip appropriately,” Craig advises.
Sunday (Part II) at Dante's
If shoegazing feels too tame for a Sunday night and you’d prefer to dance with the devil at Portland’s quintessential rock and roll club, why not tempt yourself with the longest-running burlesque show on the West Coast? Fifteen years and counting, Sinferno—snakes, ecdysiast acrobatics, fire dancers—is synonymous with the Sabbath in Old Town.
Check these off your list:
▶ Sunday night also means that it’s the service industry’s turn to be served, a fact Sinferno welcomes with open arms (and legs).
▶ While Voodoo Doughnut across the street is notorious for its harebrained concoctions, Lonesome's Pizza (which provides the pies for your sinful trysts) stuffs both its crusts and boxes with original combinations of ingredients and art, respectively.
▶ Take heed of the words of the famous Florentine written above the door: Lasciate ogni speranza, voi ch'entrate. Which these days likely means something like: Go big or go home.
