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DINING
Des Moines Register
Address: 108 E. Monroe St., Pleasantville
Phone: (515) 848-3742
Website: checkerboardrestaurant.net
What started out as a joke between friends about starting a pizza restaurant has become an anchor in Pleasantville for more than four decades.
After the laughs subsided, Ron and Karen Fee decided that maybe opening a pizza place in their small town of Pleasantville wasn’t as crazy as it sounded. With the help of friends and family, including their daughter Rhonda (who was 12 years old at the time), the Fees opened the Checkerboard Pizza Shack in 1975.
“The name came about from the red-and-white checkered tablecloths and curtains,” said Rhonda, who is now Rhonda Zimmerman after getting married and is also the current owner of the restaurant since 2010.
In the beginning, the Fee family operated the business in a rented building and focused on pizza and arcade games. (It was, after all, the 1970s.) At first, Ron tried working his day job and then working the restaurant at night, but it wasn’t long before he had to run the business full-time as it quickly took off.
“We relied on family and friends in the beginning because we couldn’t afford to hire people,” said Zimmerman. “We were fortunate that our family and friends worked for food.”
A year after opening, the family had the opportunity to purchase two buildings across the street from their current location. They shut down operations for six weeks, and Ron remodeled the old building into the current restaurant.
“As our business grew, we expanded the menu and decided that we were going to change our name to Checkerboard Restaurant,” said Zimmerman.
The Western theme can be seen everywhere from the decor, including wagon-wheel lights and Karen’s antiques like Roy Rogers memorabilia, to the names of the food they now serve, from the “Trail Starters,” which include their famous homemade onion rings, to Ronnie’s Wild West Dinners to their pizzas, which have been rebranded as “Corral Pies.”
To say the Checkerboard is a family affair is putting it mildly. Even though Zimmerman purchased the business, her parents still continue to work there. You can usually find Ron in the back making pizzas and Karen at the cash register.
“This is a business that wouldn’t have been successful without the help of family,” said Zimmerman.
Ron and Karen’s parents, siblings, children, grandchildren and great-grandchildren have all helped out at the restaurant at some point. And Rhonda actually met her husband Marty Zimmerman at the restaurant, which also provided the perfect venue to exchange vows. Yes, they got married in the restaurant.
Zimmerman admits that things haven’t been easy the past few years. Like many small businesses, they are struggling with supply shortages, rising costs and keeping staff. However, she remains optimistic. “We hope to make it to our 50th (anniversary), which will be in July of 2025.”
Distance from Downtown Des Moines: 27 miles
Hours: 4-9 p.m. Thursday-Sunday.
Kids: Look for the “For the Little Cowpokes” section on the menu. Grandson Noah recommends the chicken fingers, while Ethan suggests the mini corn dogs.
Stoplight: The Fees like to brag that the very first stoplight in Pleasantville was installed outside the Checkerboard on Oct. 27, 1984. The light is actually used to show whether or not there is a wait to be seated, although the menu admits, “So far no tickets have been issued for walking thru a red light.”
Memories: Mike Fee, Ron and Karen's son, was a part of the restaurant until his death at age 27 in a car accident. The family continues to keep his memory alive with his photo and memorabilia at the restaurant.
While You’re There: You may not realize that the very first Smokey Row Coffee Co. was in Pleasantville – and it’s still there. Head downtown and you can’t miss it. Grab your favorite coffee drink or lunch and a treat at the old-fashioned soda fountain before heading to the Checkerboard for dinner. You could also visit the Grape Escape Vineyard & Winery for a tasting in their tank room or under the gazebo.