Chess Squares – Easy and Irrestible

Chess Squares are an easy variation of Chess Pie, with a buttery shortbread crust and a sweet chess pie filling. They’re made from just a few simple ingredients, so they’re easy to make and taste divine!


Here’s the thing about Chess Pie, which leads to this recipe for Chess Squares. The recipe comes from simple ingredients that you would typically have in your home—butter, eggs, flour, sugar, and the unique twist on Chess Pie: cornmeal and vinegar.

Chess Squares are an easy variation of Chess Pie, with a buttery shortbread crust and a sweet chess pie filling.

Many years ago, folks didn’t just up and run to the grocery store every time they were out of something or wanted to try a new recipe. They had to make do with what they had on hand. Even when I was growing up, actually going to town was an event because we lived about ten miles outside of town.

Chess pie bars in a sheet pan.

Yes, of course I went to town every day to go to school, but that was just school and back. Shopping was a whole ‘nother story. We would usually only go to the grocery store on Saturdays, and maybe visit a couple of the small clothing shops.

But big shopping trips—well, that only happened a couple of times a year. We’d load up the car with my Granny, my two great-grandmothers, my mother, sister, and me, and we’d all go to either Columbus or Albany.

Chess squares with powdered sugar on a stand.

The trip was always planned weeks in advance because you had to get your green stamps in order. I loved lickin’ and stickin’ the green stamps in the books and Mama and Granny always promised I could get something at the store if I helped with the stamps. Maybe they didn’t love doing it so much!

Chess pie bars on platter.

Shopping at the S&H Green Stamp store was like shopping with free money. Even though they had received the stamps as reward for purchasing groceries, it still felt like you were getting something for free, and they always picked out things they would never otherwise purchase.

After spending all our green stamps, we’d head to the mall, just to go to Sear’s and JC Penney’s, not for shopping in the whole mall. I don’t remember going to any other stores because everything you needed could be found in one of those.

Chess squares without powdered sugar on platter.

My favorite part of those long shopping days was lunch, which was always at the same place: Shoney’s Big Boy Restaurant. Oh, this was such a treat!

Chess squares with chess pie filling and buttery shortbread crust on cake stand.

My eyes were always way bigger than my stomach and I wanted everything—hamburger and fries, Coke, salad from that amazing salad bar, strawberry pie, and hot fudge cake! Of course, my Mama never let me order all of that but those were all my favorite things and I pretty much never deviated. I ALWAYS ordered a burger and fries when we went out. I was a little bit of a picky eater back in the day and I just liked what I liked and not much else.

I did love Chess Pie though, so I’m sure I would have liked a chess bar or chess squares, whatever you want to call them. And now I love these Chess Squares!

Buttery shortbread crust with chess pie filling.

Chess Squares Recipe

A lot of people use buttermilk in Chess Pie but I never have. I use an old recipe that just calls for melted butter, sugar—which I changed to brown sugar, and eggs. Then you add just a tablespoon each of flour, cornmeal, vinegar, and vanilla, along with a pinch of salt. Rather than a pie shell, the filling is poured over a buttery shortbread crust, giving these Chess Squares just the right texture for a great hand-held snack.

Chess Squares are an easy variation of Chess Pie, with a buttery shortbread crust and a sweet chess pie filling.
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Chess Squares
Prep Time
30 mins
Cook Time
50 mins
Total Time
1 hrs 20 mins
 

Chess Squares are an easy variation of Chess Pie, with a buttery shortbread crust and a sweet chess pie filling. 

Course: Dessert
Cuisine: American
Yield: 16 squares
Calories: 320 kcal
Author: Lucy
Ingredients
Filling
  • 1 stick unsalted butter melted
  • 1 cup light brown sugar
  • 3 eggs
  • 1 tablespoon cornmeal
  • 1 tablespoon white vinegar
  • 1 tablespoon all-purpose flour
  • 1 tablespoon vanilla extract
  • ½ teaspoon salt
Shortbread Crust
  • 2 sticks unsalted butter, softened and diced into chunks
  • 2 1/2 cups all-purpose flour
  • 1/2 cup brown sugar
  • 1/2 teaspoon salt
  • 1 vanilla bean
Instructions
Crust Instructions
  1. Preheat oven to 350. Line a 9x13 inch pan with foil, allowing the foil to hang over the sides, and lightly grease the foil.
  2. Whisk flour, sugar, and salt in a large bowl. Scrape in seeds from vanilla bean and mix into flour. Work in butter. Press into prepared pan. Bake 20-25 minutes until lightly browned. Allow to cool for 10 minutes.
Filling Instructions
  1. While shortbread is baking, make the filling. Add brown sugar to melted butter and whisk until smooth. 

  2. Add the rest of the ingredients to the brown sugar and whisk until smooth.

Putting It Together
  1. Allow crust to cool for 10-15 minutes, then gently and slowly pour the filling over the warm shortbread crust. Bake for another 20-25 minutes until top is lightly browned and filling is not jiggly. Remove from oven and cool pan on a wire rack for one hour before removing foil. Then gently pull out the foil and slice the pie into squares.

 

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