Settling into a plush booth at Sayler’s Old Country Kitchen, I was snacking on the little veggie spread, of carrots and mini corn, that has come with every dinner there since time immemorial, when I couldn’t help overhearing the conversation at the next table over.
It was a father and his grown daughter telling the waitress that Sayler’s, famous for its iconic T-bone steak sign hovering above Southeast Stark and 105th, had been their spot since she was a little girl. The waitress, in turn, shared she had been working there for decades, and that all her children, save one, had also worked at Sayler’s.
With that, dad and daughter set down their steak-shaped menus, and ordered the same ribeyes with all the fixins they always had.
Steakhouses are quintessential and timeless—a comfort of meat, potatoes, and high-backed leather seating. For many of us, anniversaries, birthdays, and holidays call for a thick-cut slice of prime rib and a cloud of mashed potatoes. In a world, and a city like Portland in particular, where chasing the hottest dining trends is the rage, it is steakhouses that endure.
Steakhouses are our culinary time capsules. In Portland, our big three are all well past the age of collecting a social security check: Ringside Steakhouse has been open since 1944, Sayler’s since 1946, and Clyde’s Prime Rib celebrates its 70th birthday this year, opening originally in 1955.
“Personally, I love an old school steakhouse for the vibe,” says Ox chef and co-owner Gabrielle Quiñónez Denton. “The music from another era, the ambience, and the comfort of the familiar menu. They all provide a feeling of nostalgia that reconnects me to my long gone grandparents and others of that generation, and that makes me happy.”
Ringside, which is pushing 81-years-old on West Burnside, is Quiñónez Denton’s favorite old school steakhouse. She says she and her husband / Ox co-owner Greg Denton always start with a house martini, prawn cocktail, Ringside’s iconic onion rings, and a Caesar and a wedge salad. Then she gets the filet mignon with sliced raw onion, tomato, and a side of sauce hollandaise, while he gets the ribeye with baked potato.
At Ringside, General Manager Geoffrey Rich says the menu items may stay largely the same, but for that reason, quality control remains critical. The team conducts prawn tastings three to four times a year, making sure they’ve got the fattest and most firmly textured shellfish, which they poach in house with herbs and aromatics, before serving with housemade cocktail sauce. Ringside’s onion rings were given a stamp of approval by James Beard decades ago—nothing is going to change their sweet, flaky, oversized ‘O’ of perfection now.

“To a certain extent, everyone wants a certain security and consistency,” Rich said. “Knowing what you’re getting is an important thing, and nowhere delivers that more consistency than a steak and potatoes place.”
I am low-key obsessed with the down-hominess of Sayler’s—a more moderately priced option, where your New York strip dinner comes with a salad, crudités, bread and individually-wrapped butter pats, and a little scoop of ice cream at the end. A wooden plaque on the wall counts the over 1,000 people who have attempted their long-running challenge to eat a full 72-ounce steak with all those fixins in one hour. The Sayler family still owns the restaurant.
Ringside is so lovely: It originally opened as an Italian restaurant before being converted to its steakhouse format in the early 1950s. The fireplace was built by the original owners, Wes and Bev Peterson, in that decade. (“If you come into our restaurant and look around and something looks old, it probably is old,” Rich says.) Their 34-ounce dry aged bone-in ribeye for two (your typical cut is 12-16 ounces so this bad boy is huge) is a feat of master steakery, a testament to the 100-200 steaks the kitchen puts out each night.
My heart also belongs to Clyde’s Prime Rib, in the castle-shaped building on Northeast Sandy and 54th Avenue. There’s a suit of armor in the lobby, good jazz and blues in the bar, and a top-notch slice of rare prime rib with my name on it. Our friend group tradition was to drink copious vodka martinis (shaken or stirred, we don’t care), eat prime rib and shrimp cocktails, then go see the latest James Bond release at the now-departed Roseway Theater.
Even some of the longest-lasting restaurants of Portland’s food revival in the late '00s and early 2010s are steakhouses. Laurelhurst Market, which boasts an ethical farm-to-table approach, has been open since 2009, while so many other ventures from that era have fallen away.
Ox, an homage to the wood-fired meats of Argentina, opened in 2012, and has stayed packed ever since. The skirt steak and ribeye tie for the most ordered dish, but their famous bone marrow clam chowder, served with a beef marrow bone protruding like a ship’s mast from the bowl, is a close second, Quiñónez Denton says.
“We’ve always strived to be the place that is just as satisfying to the person who just wants your standard steak and potatoes as it is to someone who’s excited to try something a little different, such as sweetbreads or blood sausage or beef tongue or tripe,” she says.
Rich, the general manager for Ringside, says that it was a relief for the restaurant to make it through the difficult COVID closures and rebounding reservation numbers. He says there’s no plans for Ringside to go anywhere anytime soon.
“We saw the fragmentation or disintegration of being in shared spaces with friends, family, and other people,” he says. “We didn’t realize how important that was until we lost it for a significant period of time. I’m not going to take that for granted anymore.”