Goodbye, Skyscrapers: Northland loses a Winstead’s diner after nearly 27 years

Homegrown Winstead’s diner once had more than a dozen locations throughout the metro.

But in recent years it has been closing restaurants rather than expanding.

Now a location at 6260 N.W. Barry Road has shuttered after nearly 27 years.

David Haddad, president of Haddad Restaurant Group, owners of Winstead’s, said the lease expired and his landlord wants to redevelop the property.

According to the Kansas City Star archives, Winstead’s has its roots in the Depression.

Kathryn Winstead had lost her job at a bank and her sister, Nelle, borrowed funds from her boss to start a root beer stand. Summer sales were good but the sisters worried with winter coming on. So they had their butcher experiment with meat blends for a new steak burger mix. Could this have been the real start of the “better burger movement?”

Nelle later married Gordon Montgomery and the couple traveled around, looking for a place to open Winstead’s. While the sisters were afraid of political boss Tom Pendergast, they choose Kansas City for Winstead’s new home and leased space near the Plaza.

Gordon Montgomery once said: “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.”

They added french fries in 1957. Until then, customers picked them up at other restaurants and brought them along.

Inside, it only had seating at 10 booths and two counters. The real action was in the parking lot, where the servers tried to get to the cars before the cars even stopped.

It once was more of a regional chain with locations in Sedalia, Illinois and Indiana. By 1988, when it was purchased by Haddad, there were 13 locations. It also was popular for its breakfast and Skyscraper sodas and milkshakes serving two to four people.

But locations closed, including two in 2017 — at 8036 Metcalf Ave. in Overland Park and at 8817 Shawnee Mission Parkway in Merriam. It now has locations east of the Country Club Plaza, Blue Springs, Leawood, Lenexa and Overland Park.

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