Let’s Review Winstead’s!

Let’s revisit Winstead’s!

Winstead’s is a regional burger chain that was founded in Springfield, Illinois in 1936. After filing for bankruptcy in 2020, the chain is now down to two locations in Kansas City, MO and Overland Park, KS.

The chain sells steakburgers, breakfast, sandwiches, salads and milkshakes.

Over the years, Winstead’s has gained much publicity. The Food Network hailed the steakburgers as the best burger in Kansas. Food critic and The New Yorker writer, Calvin Trillin, went as far as to call Winstead’s as the best hamburger in the world.

Those were big claims from big names. So my family and friends had to find out for ourselves.


We arrived at the restaurant with big crowds, plenty of staff, and long lines in the drive through. We opted to dine in instead of waiting in the car.

Many of the benches and chairs in Winstead’s have probably seen better times. One booth was closed as there was a hole that, I believe, was a portal to another dimension where (spoiler alert) people consider Winstead’s to be the best burger.

Let’s get down to business. I ordered the double Winstead and asked for “everything” which was mustard, ketchup, pickle, and onion. I also asked for most of the extras, including lettuce, tomato, bacon, mayo and grilled onion.

In fact, everybody ordered a Winstead and not a single person was all that impressed with it. The burger was bland, dry, and all the extras ordered were probably a saving grace in pushing me through to finish it. Many comments around our table centered on how Freddy’s just blew Winstead’s out of the water.

My daughter had the grilled cheese with fries. No lie, Winstead’s may have the worst fries in the world.

The tater tots, though, were great and extra crispy.

One thing that caught my eye on the menu was the Skyscraper Shake, which we were told was big enough to feed 2, 3, or 4 people. I went ahead and ordered one with chocolate and strawberry.

The staff brings out the Skyscraper Shakes by walking it down the aisle and singing a jingle, making a spectacle of it. When it arrived, it was easily one of the largest shakes I’ve ever seen and felt like it was bigger than a baby.

This was, no doubt, the best thing we had at Winstead’s. Everybody grabbed a spoon, a straw, even hands were an option, as we did our best to finish the Skyscraper Shake.

While the burger was bad, the service may have been worse.

When we walked in, the average age of the diner appeared to be roughly in the 60s. With how slow everything was, I felt Winstead’s aged me into the 60s. We saw servers talking and chatting while food was on the counters to be delivered to customers. It took nearly an hour for a burger, with our server not even checking on us until right before the food came out.

That or our original order disappeared into the other dimension in the bench with the hole and had to be remade.

Either way, we can’t agree with The Food Network or Calvin Trillin.

Here’s their menu:

Happy Dining,

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