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checkerboard sandwich cookie

Checkerboard Sandwich Cookies

  • Author: Glenda Embree
  • Prep Time: 150 minutes
  • Cook Time: 8 minutes
  • Total Time: 2 hours 38 minutes
  • Yield: 18 sandwich cookies or 36 individual cookies 1x



For the Cookies:

  • 1 cup butter
  • 2 cups sugar
  • 2 eggs
  • 1 Tablespoon vanilla
  • 3 ½ cups flour
  • 1 teaspoon salt
  • 1 teaspoon baking soda
  • ½ teaspoon baking powder
  • ½ cup cocoa powder

For the Buttercream Icing:

  • 3/4 cup butter
  • 1 Tablespoon vanilla
  • 1 Tablespoon milk
  • 6 cups powdered sugar


  1. Cream together butter and sugar in a large mixing bowl.
  2. Beat in the eggs and vanilla.
  3. Add the dry ingredients and continue to mix until you have incorporated all the ingredients into a
  4. consistent dough.  The dough will be a little shaggy, but completely mixed.
  5. Turn the dough out onto a silicone work surface (mat) or a piece of parchment paper.  You don’t
  6. want to work any more flour into the dough, so don’t flour your countertop.  Even wax paper may
  7. work.
  8. Knead the dough for about 15  to 30 seconds to get it into a smooth ball.
  9. Divide the dough in half and set one half aside.
  10. On your kneading surface, add the cocoa powder and work to knead it into one of the dough halves. 
  11. It will take 1 or 2 minutes to get it completely incorporated so you have a smooth, glossy chocolate ball.
  12. On a clean sheet of parchment, or on a silicone baking mat, press the chocolate dough half into a rectangle ½ inch thick and about 10 ½ inches x 5 inches.  Lift the mat (or parchment onto a baking sheet and set aside.
  13. On a second sheet of parchment, or on a silicone baking mat, press the plain dough half into a rectangle ½ inch thick and about 10 ½ inches x 5 inches.  Lift the mat (or parchment onto a baking sheet.
  14. Place both baking sheets in the freezer for 15 minutes or in the refrigerator for 30 minutes.
    Once the dough is chilled and easy to work with, remove it from the freezer or fridge and begin to form the checkerboard pattern.
  15. Start by laying one slab of dough on top of the other.  It doesn’t matter which is on top, only that the colors are alternating.
  16. Slice the stack of dough down the middle lengthwise, dividing it into two equal halves.
    Now, cut through the entire stack, lengthwise, dividing that into thirds.  (I would say EQUAL thirds, because that is the goal.  But, seriously, be as precise as you can without sweating it.  These are for your family and friends and they are going to swoon at your creativity and how wonderful these taste.  If you were making them to sell, then I’d say, “You bet, measure everything down to the millimeter and have it exact.”  That, however is not what we’re doing, today. )
  17. There will be three long strips of stacked dough, now.  Pull the one from the center, flip it completely upside down and set it right back in the center.
  18. Gently put pressure on the outside layers to begin forming them into one solid block.  Flip the block a quarter turn and do the same thing.  You want all the layers to begin to meld together.
  19. Place the log back in the freezer for 15 minutes (or fridge for 30).  NOTE: I have never removed the dough from the silicone mat this entire time.  If you are using parchment and it is ripped or torn from the slicing, you may want to put the block onto a clean sheet before sticking in the freezer.
  20. After the correct amount of chilling time, remove the checkerboard block from the freezer and slice off cookies and bake.
  21. Cut the cookie log into ¼ inch slices.  Put 12 cookies to a cookie sheet. (The recipe typically makes 3 dozen for me, so I fill 3 sheets at once, putting 2 back in the fridge or freezer until time for them to go in the oven.)
  22. Bake at 350° for 8-11 minutes, depending on your oven and whether you want the cookies soft or crunchy.  We opt for soft.
  23. Remove from the oven and place the cookie sheet on a cooling rack for 2-3 minutes to allow the cookies to finish setting up.  Then transfer them to the rack to finish cooling.
  24. To make frosting, beat all icing ingredients together with a hand mixer or in a stand mixer, until a thick creamy frosting has formed.
  25. To make the sandwich cookies, spread the bottoms of 18 completely cooled cookies with ¼ inch of buttercream frosting.  (You could color the frosting or flavor it, if desired.) Top with a second cookie.
  26. Optional: I crushed 2 candy canes and pressed the sides of each cookie into the crushed candy cane dust to decorate the outsides.
  • Category: Desserts, Cookies
  • Cuisine: American