The Skyscraper shake—a towering monument to mid-century indulgence—helped solidify this Kansas City institution after it arrived on the scene in 1940. While founder Kathryn Winstead opened her very first drive-in years prior in Springfield, Illinois, she built her brand’s lasting legacy right here on thin, griddle-seared steakburgers. This iconic Country Club Plaza outpost was the first in the chain to feature the striking Streamline Moderne curves that still turn heads today. Order yours with a side of crinkle-cut fries, and settle into an aqua booth where the vintage nostalgia gleams and the milkshake machine never stops.
winsteadssteakburger.comPart of: Old Time Eatery Guide