Founded in 1936 in Springfield, Illinois by Kathryn Winstead (with the help of her sister Nellie), Winstead’s was one of the first drive-in restaurants in the United States. Customers would back into a stall, flash their lights, and a car hop would come out, take their order, and deliver their food.
It all started halfway through the Great Depression when Kathryn Winstead lost her job at a bank, and her sister, Nellie, borrowed money from her boss to start a root beer stand. While summer sales were good, the upcoming winter had them concerned. So, they asked their butcher to experiment with meat blends. The result was to become the Winstead’s steakburger.
Originally from Smithton, Missouri, the Winstead family wanted to return to its Missouri roots. With the help of another sister, Fannie Winstead Garst of Sedalia, Missouri, Kathryn and Nellie opened Garst’s Drive-In in Sedalia in July 1937—the first drive-in restaurant west of the Mississippi River.
Soon after, Kathryn, with Nellie and her husband Gordon Montgomery, decided to open a Winstead’s in Kansas City, Missouri. They found an ideal location near 47th and Main Streets, just east of the Country Club Plaza. Under the watchful eyes of political boss Tom Pendergast and real estate developer, J.C. Nichols, Kathryn and Nellie opened their new Streamline Moderne-styled store in 1940, accommodating both car-hop service and inside dining.
Said Montgomery, “People made fun of us poor country kids trying to sell 10-cent burgers when other places sold six for a quarter. We made enough money the first year to buy the place.”
Struggling through the beef rationing of World War II, the restaurant flourished in the years following the war. It also expanded, adding locations in Lee’s Summit and Independence, Missouri.
Kathryn Winstead retired from the restaurant in 1952. Nellie and Gordon Montgomery continued, adding French fries and milkshakes to the menu in 1957. Kathryn died in 1967, and two years later, the Montgomery’s sold Winstead’s to brothers Morris and Victor Lerner, who owned Kansas City’s King Louie International. The Lerner’s opened two new Winstead’s locations – one in Kansas City North and the other in Overland Park, Kansas.
In 1982, the Lerner family sold King Louie International to an investment group. Today, a local restaurateur, Nabil Haddad, a franchisee and major stockholder in the McDonald’s corporation, oversees all remaining greater Kansas City Winstead’s locations.
LUMI’s Winstead’s sign is from the now-shuttered location at 6260 N.W. Barry Road. The wall-mounted wordmark was designed to complement the original 1940 deco influence. The Barry Road location closed in 2018 after 27 years in business.
Famous for its steakburgers and skyscraper milkshakes, Winstead’s earned Food Network Magazine’s recognition as the “Best Hamburger in Kansas.” Yale food critic Calvin Trillin named it the “world’s best cheeseburger.”