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All things are impermanent. Bars and taverns are organic, living creatures, and no matter how good they are, sometimes they change hands and go bad. Cluelessly sanitized and genericized. Or, occasionally, they’re bad to begin with and instead get much better. Here are three examples of that kind.
The Checkered Flag II
You know a joint had a bad reputation when it officially changes its name to “the new” or adds the Roman numeral II. The Checkered Flag wanted such a fresh start it did both, depending on whether you read the name online or IRL.
Before 2019, the Checkered Flag at Southeast 82nd Avenue and Flavel Street was a Pacific Northwest Bukowski wet dream. Cheap motel-style apartments shared a parking lot with the most lowdown bar in Portland, its mailboxes literally bolted alongside the tavern door. For week-to-week or hour-to-hour, the cinematically named Del Rancho Motel and Dar-Ron Motel sit catty-corner. The scene at the old Checkered Flag was what you’d expect. I loved to drop in when erranding down that way for the raggedy pool table and a beer. It wasn’t merely a scuzzy bar—there’s plenty of those on 82nd—but a scuzzy bar with character.
Here in 2025, many a Thursday evening finds me driving 20 minutes directly to The Checkered Flag II because its socials post the week’s menu by resident bartender and cuisinologist Lizzy on Facebook. Always a genius construct of Instant Pot, smoker, air fryer and Crock-Pot goodness, the kind that gets better with time. Example: three pieces of chicken, brined overnight, smoked six hours, then air-fried and served with mac and cheese, collard greens, ham hocks, smoked and baked beans, and cornbread. Price tag? Twenty bucks. On Mondays, bartender-cuisinologist and karaoke host Bryce serves up his own giant pot of soup, stew, chowder and/or gumbo…consistently real, substantial meals at a fair price that put any other dive bar’s mini-corndog bullshit to shame.
The wraparound enclosed patio creates a clean and secure feeling, not to mention a dank tiki vibe (occasionally with the aforementioned meats smoking or Crock-Pots stewing). Appropriately, the roof is decked in flags, specifically: Old Glory, BLM, and rainbow—which seems like “uniting, not dividing” to me. Anyone who disrespects those three concepts of unity gets permanently 86’d, no matter how regular or how new.
The beauty of it all is, the New Checkered Flag lost no character, destroyed no artifacts, removed nothing but dust and grease and urine stains while preserving the accumulated personality of a neighborhood bar. Even plenty of regulars remain, or the nice ones anyway… 7483 SE 82nd Ave., 503-771-1994, facebook.com/checkeredflag.pdx. 11–2:30 am daily.
O’Dear Bar & Grill
The neon white-on-black art deco sign for O’Dear Bar & Grill is so reminiscent of Ciro’s nightclub on 1930s Hollywood Boulevard that it’s almost too classy for Sandy. But it sits across the street from the Dollar Tree and Grocery Outlet, and a few times a year someone gets shot in that general neighborhood, which keeps things real.
Before closing in 2015, the space was called Winners Motorsports Bar, and not only had a full racecar body perched on its marquee, but a full racecar body hanging on the wall inside. It also had two maroon felt pool tables straight from Rick James’ garage sale, accented on each corner pocket by large brass lion heads. In 2018, serial bar operator Vince Culp (2nd Street Bar in Gresham and Whiskey Tango in Hood River) took over and heavily renovated it with his sons, rechristening it the O’Dear. The cars and funky pool tables are gone and, instead, there are three (free) Diamond pool tables, a separate music room, and a cool upstairs balcony loft that’s available for private parties. Like I said, classy stuff.
Today, walking into O’Dear is like entering a Disneyland ride. It somehow feels bigger inside than outside. What’s not an illusion is the bar’s signature shrimp and grits. You know other places where the bowl is a foot in diameter but only a half-inch deep? Here it’s an actual real-life large bowl. The shrimp are huge, the andouille sausage is generous, and I wish I could buy the spicy-smoky red sauce in bottles to spread on everything at home.
Downside of the O’Dear? The bar relies on Spotify streaming for the tunes so patrons can’t adjust the vibe, and when staff is busy it can drift into a sludgy algorithm. A jukebox vendor would clean up there. 10810 NE Sandy Blvd., 503-477-8182, odearbar.com. 11:30–1 am daily.
Covert Café
The perfectly named Covert Café is what happens when your cool neighbors start a bar in their backyard that just keeps expanding. Watch it unfurl on Google Street View from 2018 to 2025, when a hidden, kitchenless nook called Growler’s Taproom started growing decks and walls and food carts and a kitchen addition and a name change. Or skim Covert Café’s socials with many nights of Star Trek trivia, D&D, music and comedy.
And now, bubbles.
That’s what happened when I found myself at the recent Portland Adult Soapbox Derby afterparty (the bar’s fourth year entering) and met owners Joe Rodgers, Joe Mishkin and Cody Scoggins. We made giant soap bubbles with fishing rods and cotton rope, solution and the summer breeze. We agreed that for humans, creating and watching bubbles is not too different from creating and watching a campfire with the mesmerizing color flashing, the environmental airflow-balancing skills, and the primal-nerve-stimulating brain stuff…and also agreed that no other bar in Portland offers free bubbles. Since everyone fucking loves bubbles, it’s a no-brainer; this is now the first bubble bar.
Even without bubbles, there are stacks of games everywhere, and metal tavern puzzles and oh-so-much Star Trek memorabilia. The bar even serves a Star Trek hazy IPA, Deep Haze 9, custom-brewed by StormBreaker, available only here. And for the love of Spock, be sure to order the signature bacon jam. The lush and velvety concentration of bacon and onions takes 16 hours to make, comes with slices of sourdough toast, and costs $6. 803 SE 82nd Ave., 503-254-8277, thecovertcafe.com. 4 pm–midnight Monday–Friday, 11 am–midnight Saturday–Sunday.
