Deep Dive: Our Guide to Southwest Portland’s Dive Bars

Despite downtown disturbances, a fire in Multnomah Village, and rapid development, Southwest Portland’s remaining dives refuse to die.


Cheerful Bullpen

1730 SW Taylor St., 503-222-3063, 9 am-9 pm daily; open later after Portland Timbers and Thorns matches.

Established: 1948

Since opening 75 years ago, Cheerful Bullpen has been a neighborhood bar in every sense of the word. And as the neighborhood around it has changed—with the Timbers and Thorns taking their respective leagues by storm, and high-rise apartment buildings now surrounding the pub—so has the Bullpen. In the earliest days of the COVID-19 pandemic, that meant converting the front of the bar into a convenience store with refrigerators full of soda and Labatt Blue (the latter a preferred beer of Buffalo Bills fans who pack the bar for every game). More recently, adaptations have included advertising to students at nearby Lincoln High School—yes, minors are welcome—with promises of short wait times for burgers and other pub grub, loyalty punch cards, and an in-house espresso machine. When school’s not in session, you’ll drink with pregaming soccer supporters (Providence Park stands almost directly across the street), passionate football fans (Bills merch covers the walls), and laid-back locals enjoying daily specials—like $5 pints of craft beer on Mondays and $10 patty melts on Wednesdays. Savor it all on the spacious back patio or at one of the picnic tables out front. MATT WASTRADOWSKI.

Cheerful Tortoise

1939 SW 6th Ave., 503-224-3377, 9 am-2:30 am daily.

Established: 1951

Surrounded on all sides by Portland State University buildings, Cheerful Tortoise checks all the boxes required of a classic college dive bar without ever feeling formulaic. As finals approach, you’ll see college students studying next to the window—the brightest spot in the bar—while noshing on wings and sipping regional craft beer or cider. When school’s out, the bar livens up with bustling karaoke nights on Wednesdays, Fridays, Saturdays and Sundays. There’s also a well-worn shuffleboard table, occasionally intense rounds of Big Buck Hunter Reloaded, and daily drink specials that range from $7 bloody marys every Sunday to $5 glasses of wine each Thursday. Despite the bar’s close proximity to PSU, it’s not all college kids. Depending on the time of day, you might rub elbows with nearby office workers, travelers looking for downtown nightlife, and servers fresh from the night shift. MATT WASTRADOWSKI.

Goose Hollow Inn

1927 SW Jefferson St., 503-228-7010, 11 am-10 pm Sunday-Tuesday, 11 am-11 pm Wednesday-Saturday.

Established: 1967

The Goose Hollow Inn is a staple of the cozy Goose Hollow neighborhood, and the warm, down-to-earth pub is perhaps best known for its longtime owner: late beloved Portland Mayor Bud Clark, who opened the tavern in 1967. (His daughter, Rachel, still runs the joint.) Little has changed since father handed the operation to daughter; the inn offers the best of what nostalgic Portlanders call “Old Portland,” thanks to its cluttered yet charming décor, strong drinks, one helluva Reuben sandwich as well as servers and bartenders who are nice but not too nice. The hot buttered rum is to die for, especially on a rainy afternoon, but you really shouldn’t overlook the pub grub—from the garlic bread to the pizza with a generous amount of toppings to the potato salad. But we’re all about the classic Reuben ($15.50, but worth it) and the hearty crab melt if you’re looking for a meal. The inn doesn’t skimp on the cheese or the protein. SOPHIE PEEL.

Goose Hollow Inn (Aaron Lee)
Goose Hollow Inn (Aaron Lee)
Goose Hollow Inn (Aaron Lee)

Kelly’s Olympian

426 SW Washington St., 503-228-3669, 5 pm-2 am Monday-Friday, 1 pm-2 am Saturday-Sunday.

Established: 1902

Kelly’s Olympian has been a downtown institution for as long as anyone can remember, and it looks the part. Newspaper clippings documenting the bar’s long history and its impressive list of regulars are on display, and vintage motorcycles hang from the ceiling. But if the décor inside hasn’t changed, the environs outside certainly have. The vacant office complex across the street became a haven for fentanyl users and their dealers during the pandemic, and the bar has felt the strain. It’s hanging on “by a string,” owner Ben Stutz told WW earlier this year. Kelly’s had to remove its COVID patio out front after someone built a bonfire on it, one of the bartenders says. True to form, staff tore it down and replaced it with motorcycle parking. Still, the bar’s central location and long history make it a favorite spot for out-of-town gawkers, and the prices reflect it. Fortunately, that hasn’t kept away regulars, who say it’s still the best place to drink downtown. On a recent Friday afternoon, some of those longtime customers were smoking on the new benches out front and meting out advice: Liquor up for cheap at the Jockey Club around the corner, and then come to Kelly’s to take in a punk show or nurse a beer with friends. LUCAS MANFIELD.

Kelly's (Brian Burk)
Kelly's Olympian (Brian Burk)

Leaky Roof Gastropub

1538 SW Jefferson St., 503-222-3745, 10 am-9 pm Wednesday-Friday, 9 am-9 pm Saturday, 9 am-3 pm Sunday.

Established: 1947

The names of two Goose Hollow bars apparently fool newbies: I’ve overheard multiple phone calls at Goose Hollow Inn involving people looking for a room, while a bartender at the Leaky Roof says some customers walk in expecting to be led to a rooftop patio. (I guess no one assumes pitchers are warming up at the nearby Cheerful Bullpen.) What also might be confusing is Leaky Roof’s inclusion in this guide. After all, it doesn’t look like a traditional dive. There’s ample lighting from both fixtures and unobstructed windows; the walls are free of graffiti, TV sets and framed hodgepodges of memorabilia; and you never leave craving a shower to rinse off a layer of grime and regret acquired at some of the seediest joints. However, the deeply scuffed hardwood floors, dark-grain booths and split pea soup-green walls adequately dial down the brightness, making this shoebox-sized space suitable for silent, moody day drinking—a prerequisite for any dive. However, it’s just as good for rowdy socializing with the regulars, who will unashamedly celebrate the Oregon Ducks’ beatdown of Portland State University on the gridiron, shit talk Goose Hollow Inn (“you don’t have to be an octogenarian to come here!”), and declare their love for the staff, even if the cook did recently 86 a favorite menu item. In fact, the true sign of a dive is a blurred line between customers and staff. When one barfly ends up hosting a Christmas party at his nearby condo and the whole Leaky Roof crew shows up, you know that the division of roles is beyond blurry—it’s downright opaque. “We know each other’s days,” my bartender said of the patronage. “This is your home,” added a regular. “This is your living room.” ANDI PREWITT.

Renner’s Grill

7819 SW Capitol Highway, 503-246-9097. 9 am-2:30 am Monday-Friday, 7 am-2:30 am Saturday-Sunday.

Established: 1939

A 2018 kitchen fire could have easily ended what was then Renner’s nearly 80-year run. The collective neighborhood wailing was almost immediate. But rather than deal the area another blow by closing (nearby 84-year-old O’Connor’s pub shuttered that same year), the owners pushed ahead with a rebuild and remodel. Word of the latter prompted neighborhood grumbling, but not much has changed inside the best bar in Multnomah Village. Much of what was inside was salvaged, including artifacts documenting the bar’s history: a bank ledger, branded pens and matchbooks, an old menu advertising top sirloin, liver and onions, and sardines with potato salad. And while change is usually never good in Old Portland, the renovation swapped out Renner’s drab interior façade and oppressively dark wooden trim for blond beams that brought some much-needed warmth to the space without looking conspicuously new. Besides, you still have a reliable cast of old-timers who add their own layer of authenticity whenever they walk through the door. They’re likely drinking tallboys of PBR—”ice cold”—and looking to chat up a fresh face or another regular about anything from the demise of Andy and Bax to their garden harvest. Also expect a wide variety of locals (it really is Multnomah Village’s finest drinking establishment), which on my visit included a couple glued to the U.S. Open, young roommates downing Bauman’s Cider on the patio and an aspiring mountaineer sipping Ablis CBD. Rumor has it that you’re also drinking among ghosts. Bartenders have reported strange sightings (a longtime employee died of a heart attack here while changing a keg of Pabst), but any supposed paranormal activity typically happens late at night. If you’re here and need to temper your buzz, order the Juicy Lucy. There’s not a finer specimen of the Minneapolis-famous, molten-cheese-in-the-patty burger in Portland, which nears Matt’s Bar perfection. ANDI PREWITT.

Renners (Henry Cromett)

Rialto Poolroom

529 SW 4th Ave, 503-228-7605, 11 am-2:30 am daily.

Established: 1918, 1987

A pool hall, right near the city’s river, the Rialto has somehow soldiered along for decades as quite literally all else changed around the grande dame of downtown recreational pursuits. Hailing from the halcyon days of the early 1900s, when hustlers slinging eight balls meant rather more manageable troubles, the expansive lounge resembles a luxe sports bar and, apart from the tables available for hourly rental, hosts nightly poker games while the former card room next door takes bets on horse racing across the country and a subterranean venue books jazz and burlesque shows. The cavalcade of 19th century vices may sound unfathomably quaint, but the Rialto never feels dated. This incarnation, built beneath the former Jack London Hotel in 1987—more than three decades after the original closed—has seen continual small renovations. Moreover, ever since nightlife impresario Frank Faillace (Dante’s, Star Theater, Kit Kat Club) purchased the space seven years ago, its focus has been far less concerned with exploiting an amorphous history than subtly honoring emblems of Old Portland. Legendary jazz and soul drummer Mel Brown has a well-attended weekly revue here. Under the aegis of Epoxies guitarist Brian Kozenek, the “Electric Burgerland” menu has been streamlined: fresh-cut fries, hand-dipped corn dogs, and cheeseburgers half the size of most bars’ sloppy monstrosities at a third their price—indulgences that should cater to most appetites, which really shouldn’t seem like an old-fashioned idea. JAY HORTON.

Rialto (Rialto Facebook)
ralto-facebook (Rialto Facebook)

The Ship Tavern

7827 SW 35th Ave., 503-244-7345. 11 am-midnight Sunday-Thursday, 11 am-2 am Friday-Saturday.

Established: 1944

Some Renner’s snobs sneer at The Ship, which is just around the corner. Other regulars will quietly shuffle down the hill to the nautical-themed bar for a change of scenery. While it does lack Renner’s historical flair, The Ship offers, well, something for somebody. For starters, there is a surprisingly large draft beer selection—24 handles—along with a televised keg menu that also displays a lower-third ticker of Untappd check-ins, just like a respectable taproom. However, you’re still more likely to see regulars drinking Pabst and Rainier out of cans nestled in koozies they brought from home. There’s also plenty to look at. Given the varying quality of the skeleton pirates, decorative schooners and oars on the walls, it’s as if a tsunami deposited a Goodwill’s stock of seafaring-themed tchotchkes on the bar’s doorstep and the owners ran with it out of sheer convenience. Absent the marine motif, The Ship would just be a large, grayish box with a pool table, so at least it’s found an identity. A Renner’s drinker warned me not to order food here, and during my visit, all observed caloric intake was in liquid form, so I followed the lead of folks who’d spent far more time at this bar than I had. Perhaps that’s why BridgePort Brewing’s annual holiday Ebenezer Pub Crawl always ended at The Ship—by stop five, everyone would’ve been too sloshed to care what the food tasted like. ANDI PREWITT.

Virginia Cafe

820 SW 10th Ave., 503-227-0033, Noon-10 pm daily.

Established: 1914

That official birthdate feels a little misleading. As the initial effort of the Greek restaurateur family behind the original Jolly Roger and Spaghetti Factory chain, the first iteration of the Virginia Cafe was little more than a glorified food cart serving coffee and sammies in Portland’s West End. However, in 1922, ownership expanded the business by opening another VC on Southwest Park Avenue, which turned out to be its longtime digs. Every bar to pass the century mark has lived many lives; habitues of each era claim theirs to be uniquely golden, but the press clippings and memorabilia papering the bar’s walls imply a ‘70s-to-’80s heyday fueled by patrons who were dressed to impress. Alas, when an incoming high-rise forced the Virginia Cafe to relocate in 2008, the Last Regiment of Syncopated Drummers-led parade of patrons carrying their barstools to the new Southwest 10th Avenue location capped a precise transplant of staff and furnishings, though it never has felt quite the same. Much like the nearby Central Library branch, most of us blithely ignore the Virginia for years until we suddenly require its services. Need a downtown hideaway to catch the end of a game, or drink through a blind date, or wolf down a more than decent burger-shot combo for minimal expense? You’re damned glad the VC’s still there, you’d mourn its passing, but you still sorta hope you’ll never need to return. JAY HORTON.

Ship Tavern (Aaron Lee)
Ship Tavern (Aaron Lee)
Ship Tavern (Aaron Lee)

Yamhill Pub

223 SW Yamhill St., 503-295-6613. 10 am-11 pm Monday-Friday, 2-11 pm Saturday-Sunday.

Established: 1939

Over the past quarter-century’s upheaval of downtown—from the construction of new high-rises to the war zone status of the Southwest shopping district—what dives remained suffered midlife crises of sorts, prompting everything from the installation of a motorcycle collection on the ceiling at one to basements being overtaken by jazz elsewhere. The only constant is Yamhill Pub, which has stayed the same except more so, somehow. The interior is still enveloped by overlapping graffiti so thick that borders disappear and, like that immersive van Gogh exhibit, the tags themselves are a technicolor swirl of proclaimed identities all at once and forever. Bar conversations aren’t much different. Bartenders advise newcomers to avoid both the food and the restrooms, and the usual aroma would imply most agreed. We’re not sure where consumption ranks these days, but at the height of Oregon’s Blue Ribbon period, the saloon served more Pabst than any other bar in the state and, back when it ran through 26 kegs a week, it sometimes led the nation. TouchTunes and flat-screens aside, the pub looks just as remembered, but ever since management erected a smokers’ shed out front as a desperate COVID-era stratagem, the place has had a different feel—friendlier, happier, infinitely more inviting. Against all odds, the Yamhill crawled through a river of shit and came out clean on the other side. JAY HORTON.


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