Portland is a city with one foot in modern hipsterdom and the other planted back in a century of small frontier towns battered by rain and, well, more rain, with local taverns often holding the communities together. Even today, most neighborhoods still have a beer-and-a-shot watering hole frequented by folks of every age and type. These dive bars play host to just about anything, from punk bands and pool tables to armchairs and pancake brunches, and unlike some of our classiest restaurants, these $10 joints have never gone out of style. So, if you are a newcomer to this city, or you just turned 21, make sure you take the time to visit one of these icons of Rose City culture.
Billy Ray’s Dive
There are few sights more noticeable on the Eliot stretch of MLK than the glowing red neon sign of Billy Ray’s, which simply reads “TAVERN.” This long, cramped two-story bar with shiny red leather bar stools and booths seems to whisper “Americana” to the eclectic bunch of neighborhood locals and road-trip tourists just in to watch a Blazer game or play some pinball. While other dives in Portland have moved to cater to a wealthier crowd looking for a tapas menu and a selection of IPAs, Billy Ray’s remains the cash only, hotdog serving, $2-for-a-Rainer joint it was sixty years ago. Come in after a lover’s quarrel or getting laid off, and wax nostalgic with a bartender who is only half-listening, and half-watching for a fight breaking outside the front door. Despite its humble exterior, Billy Ray’s comes with a fairly classy backyard, a Ping-Pong table, and a cozy upstairs where you can play a game of pool, enjoy the funky wall art, and head-bang to the punk music.
Only a few blocks from the hustle of the industrial Central East Side’s club and brewery scene, this low-key dive covered in ivy, feels like it is out in the boonies. Picnic benches, a fire pit and corrugated tin overhangs turn the front patio into a village scene of drinkers and diners enjoying Roadside’s upper-end pub grub, which includes an $11 New York Steak and a kebab sampler.
Step inside and you will find a “Big Trouble In Little China” vibe with a free jukebox, mood lighting and a solid billiards table in a near-private room filled with the former stock of an antique store. In keeping with dive bar aesthetics, Roadside is cash only, but any inconvenience is worth sitting by an outdoor fire pit and listening as the summer rain tap-dances on the tin roof.
The Ship Tavern
While it isn’t always easy to get your Portland friends to cross over the West Hills into deep Southwest Portland, mentioning this 100-year-old tavern might do it. With 20+ local and domestic beers on tap, clean surfaces and a welcoming vibe, this bar seems intent on remaining the social soul of far-flung Multnomah. While the pool table is almost always taken with a dozen more quarters lined up on the felt, the Ship’s most popular form of entertainment are its sandwiches. The French Dips, meatballs subs and hot dogs will match any appetite and sit well with a hummus platter or artichoke dip. Right at the crossing of Capitol Highway and Multnomah Boulevard, The Ship draws folks from all over Southwest and serves as a way station for sports fans and storytellers alike.
Holman’s Bar & Grill
Open at 8AM and with a backyard big enough to fit all of Portland’s remaining smokers, Holman’s has long been a crowd pleaser. Located a block away from Burnside on 28th Ave, this dive is almost dead center on the Portland map. This makes it the perfect meeting place for the beginning or end of a long night, when you are most in need of their pulled pork sandwich or peanut butter bacon burger (eat at the bar for faster service). They also make a mean spicy Bloody Mary. Holman’s has been a hotspot since before my mom started exploring Portland’s bar scene, and with this stability comes a deeply felt love from its patrons, who would sooner smash the windows of their car than break one of its pool cues. Feeling that adulation as a newcomer makes a visit to this well-kept granddaddy of dives worth any effort.
While the exterior looks like something you would blow right past on your way to Vegas, the interior of this triangle-shaped bar has received such a glorious retouch that you might question placing it on any “dive” list. Yet the cozy booths, fried food, cheap drinks ($8 cocktails) and storied bar ensures that, while it might be the cream of the crop, it is at its core a neighborhood dive bar. Good for occasional live jams and even better for some karaoke, the Sandy never feels dead, even when you are the only one rocking out on the dance floor. Thanks to its recent updates, the Sandy Hut is probably the best dive in the city for a first date. Thanks to its uber-cheesy mac, it is also a fantastic lunch spot to drown your sorrows in, if last night’s date didn’t end so well.
Thanks to a unique lighting scheme, this is the only dive in Portland where Christmas lasts 365 days a year. While the Slammer used to sit by its lonesome on a corner in the heart of the East Side’s industrial district, it now serves as the last-chance bar to all the clubbers and rockers looking for a nightcap and someone to go home with. One of the smallest dives on this list, the Slammer chose to go with tabletop Pac-man and a classic skee-ball machine instead of a billiards table, making it even easier to flirt with a stranger by showing your hand-eye coordination. While the Slammer has got to have the bare minimum of food menu items required to sell booze in this state (you can build your own sandwich, however), it makes up for it with some of the best late-night playlists in town. Get ready to sing your heart out to some Elton John.
Nestled on a rundown block downtown, Kelly’s brings a little bit of glitz and glam to the dive bar formula. Looking like a biker’s bar on the outside, the inside of Kelly’s is an over-saturated canvas of color and old-timey signage. Classic motorbikes hang over the heads of a wild bunch of punks, college kids, suits, and leather-clad Harley-heads. Like any great Portland dive, the menu offers your classic chicken wings baskets, scrambled egg dishes and sammies — only Kelly’s goes even further by serving fried mac-n-cheese balls. While the music can be all over the place, from rock to K-pop, the beer is always cheap and making conversation about your bar neighbor’s snake tattoos easy.
Behind what has to be the most inconspicuous front door on a quiet cobblestone-street, is one of the most nary-a-care, true-blue garbage heap of a bar in the state — possibly the region. With foul language scrawled and scratched on virtually every surface, crowded tables, poor lighting and a toilet that looks like the one Ewan McGregor crawled into in Trainspotting – opinions about the ol’ Yamhill are split. Seriously, visit its Yelp page and almost all of the 100 reviews are 1-stars or 5-stars. Yeah, it is a bit beat down, and the bartenders have a knack for orneriness, but every true lover of The Dive knows that to be a great dive bar, first you must not give a damn about nothing.
As Portland keeps growing at breakneck speed, more and more of our favorite century-old establishments are getting torn down just as the third or even fourth generation of Oregonians start to enjoy them. Going into a truly excellent Portland dive is stepping back to a time when the towns of the Oregon Country were defined mainly by their post offices and weathered taverns, where a traveler could enjoy a glass of bourbon, chow on some smoked fish and catch up on what’s going down in their community. While the need for a post office feels more distant than ever, Portlanders will tell you that these places of brew-worship are still essential.