The history of Winstead’s in Kansas City

There’s more to Winstead’s than burger and milkshakes — there’s stories to be told, too. Dive into the history of this diner franchise and see where it stands in our city today.

Winstead's Sign KCtoday

Warning: Prepare to become hungry.

Photo by KCtoday

Table of Contents

Skyscraper milkshakes, french fries, and burgers — that’s what most people think of when they drive by Winstead’s. Today, we’re shifting that focus to what those four walls have heard and seen through the decades + where Winstead’s stands today.

Where it all began

The diner was originally a drive-in style eatery — one of the first in the US. Founded in Springfield, Illinois in 1936 by Kathryn Winstead, the restaurant biz quickly became a family affair. Kathryn’s brother, Jack, opened a second spot in Jacksonville, Illinois. Then Nellie, their sister, brought up a new idea to Kathryn.

Winsteads KCtoday

Winstead’s circa 1980s. Can you spot any differences?

Photo via Kansas City Public Library

Welcome to KC

Sometime between 1938 and 1940, Nellie and her husband, Gordon, suggested a restaurant near the Country Club Plaza in Kansas City. While Kathryn was hesitant at first, she eventually agreed to bring Winstead’s to the neighborhood in 1940. This KC spot would be the first Winstead’s designed in the Streamline Moderne style — plus, it would serve customers inside and outside via carhop.

Across the region

The Country Club Plaza was just the start of their KC legacy. A location in Lee’s Summit opened in the 1940s, followed by one in Independence in 1946. Years later, Winstead’s could be found in North Kansas City, Lenexa, and Overland Park. While today there are only three standing, the legacy of the restaurant can still be found around the metro area.

Is there an iconic Kansas City eatery, landmark, building, or era that you want us to dig up? We’ll put our detective hat on — just let us know where to start.

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