Winstead’s has been a noteworthy restaurant my entire life. I remember going with my dad, sisters and grandma after my brother was born. I grew up getting a Winstead’s chocolate shake every time I got a shot at the doctor. It became a common hang out spot for my friends and me in highschool and my siblings and I would usually go for a last day of school lunch. My parents and grandparents even grew up going there, too. Winstead’s has literally been with me through every step and phase of my life.
Located on the Plaza in Kansas City, Missouri, Winstead’s has been a KC classic since 1940. Specializing in steakburgers and shakes and malts, Winstead’s certainly has an old-American feel. The inside of the restaurant looks just like a 1940s diner with bar stool seating, a mint green and light pink color scheme, neon lights and even a working jukebox.
Besides the nostalgia, Winstead’s has some of my favorite food. My order is a double Winstead with cheese, mustard, pickle and onion. I get a 50/50 on the side with extra crispy fries and onion rings. And of course, a small chocolate shake. Winstead’s named their traditional steakburger after themself, so you can order a single, double or triple Winstead. This burger is exactly what you would expect if you know an old-fashioned steakburger, the patty is extremely thin and so very delicious. The 50/50 is a fun way to switch up the traditional burger and fries. The 50/50 lets you mix and match any of their sides so you can have half and half of fries, onion rings or tater tots.
Their shakes are one of the more popular menu items and very well-made in my opinion. They use real ice cream and mix in the flavoring of your choice. I am a chocolate girl, but I’ve also tried vanilla, strawberry, butterscotch and banana—all delicious depending on my mood. They also make malts, the perfect ode to their old-fashioned ambiance.
To make things even more interesting, Winstead’s has a menu item called the skyscraper. This is perfect for a group to share as it’s a 12-inch-tall vase full of the shake or malt of your choosing. On their menu it reads, “Enough for 2, 3 or 4,” and I would say it’s enough for even more. Everyone gets a straw, and you share! They sing a song and rattle a tambourine as they bring it to your table as well… “Skyscraper, Skyscraper coming your way *clap clap* we’re having fun the Winstead’s way.” And seriously the whole staff sings as they bring this indulgent treat to your table. They even have renditions of this song for Christmas. While this was absolutely mortifying to me as a child, I have come to love this tradition and the fact that I’ve grown up with it.
The cherry limeade is to die for, and I grew up on their grilled cheese dipped in ketchup. It’s diner food, but it’s pretty much all good. As the restaurant ages, it has some rips in the seats and some stains on the carpet but despite that, it will always feel like home to me. There’s no doubt that a Winstead’s meal can cheer me up, help me celebrate, bring connection to my friends and me and of course be the perfect late-night snack as their drive-through is open 24/7.
If you’ve been to Kansas City and haven’t tried Winstead’s, I think you need to go back. Like their menu says, they “grind U.S. Choice Steak daily for the sandwich. Authentic soda fountain treats, and table service are still a part of the tradition. And so is the fun!” I couldn’t agree more.
Ruthie's Writings. 