Checkerboard & Pinwheel Cookies

Servings : 8 dozen

These pretty cookies would impress young and old! They are beautiful in appearance and incredibly delicious too!

Recipe source: Checkerboard Cookies


  • 5 1/3 cups all-purpose flour
  • 1 tsp. baking powder
  • 1 tsp. salt
  • 1 lb unsalted butter, at room temperature (2 cups or 4 sticks)
  • 2 cups granulated sugar
  • 1 tbsp. pure vanilla extract
  • 2 large eggs, at room temperature
  • 1/2 cup unsweetened cocoa powder


Sift together the flour, baking powder, and salt. Set aside.

In a large bowl, using an electric mixer beat the butter and sugar together until light and fluffy. Beat in the eggs, one at a time, then vanilla extract. Add the flour mixture and mix to combine. Finish the mixing with your hands or a wooden spoon.

Divide the dough in half. Knead ½ cup of cocoa into one portion of the dough.

Divide the chocolate and vanilla dough in half. Form each of total four portions into a rectangle, wrap individually in plastic, and refrigerate for at least 2 hours and up to a day.

Before proceeding, take one portion of the chocolate and one portion of the vanilla dough and let them sit on the counter for about 15-20 minutes to soften slightly.

On parchment paper (preferred) or a lightly floured surface, using a floured rolling pin, roll one portion of the vanilla and one portion of the chocolate dough (separately, of course) into ½ -inch thick rectangles, with the sides about 12 x 5 inches long. Using a pizza wheel (such a wonderful tool for this job) cut out total of 9 ½ -inch wide strips from the each dough. Handling the strips delicately, form two checkerboard logs alternating the chocolate and vanilla strips (see the photo of the finished cookies). I never use an egg white or water to adhere the strips one to another. If you don’t use a lot of flour during the dough rolling it’s not necessary, everything stays together without any problem. Cover with plastic wrap or parchment paper and refrigerate until firm, at least for 2 hours.

When ready to continue, on the parchment paper roll the remaining chocolate (or vanilla) dough into a rectangle about 1/3-inch thick and measuring 12 x 6 inches. Place the firmed checkerboard log into the center, long sides parallel, and with the aid of parchment, wrap the dough around the checkerboard log pressing firmly to adhere. Roll the finished log from side to side to form sharp corners. Wrap in the parchment and/or plastic and refrigerate well. The best would be to leave the formed cookie log in the refrigerator overnight. Don’t rush if you are after the uniform shape of the cookies. Repeat with the rest of the dough and the second chilled checkerboard log to form another, opposite in colors, cookie log. Wrap, place in the fridge. As I mentioned, you can freeze the logs. Thaw them overnight in the refrigerator before using.

When ready to bake, center an oven rack and preheat the oven to 350F. Cover a large baking sheet with parchment or a silicone mat. Using a very sharp knife, slice the cookie-dough log into ¼-inch thick slices. Place on the prepared baking sheet leaving about 1 inch all way around them. Bake the cookies, in batches, for about 12 minutes until firm and golden brown on the bottom. Don’t let them bake for too long, or the color contrast between the chocolate and vanilla dough will be lost. Cool on the baking sheet on a rack for 15 minutes. Then transfer the cookies to the rack and cool completely.

Pinwheel cookies

This is a variation in the preparation of the above recipe. Using half the measurements of the same recipe, make the dough and then divide it into two equal portions. Add the cocoa into one of the portions. Refrigerate for at least 2 hours.

Roll out first the dark and then the vanilla dough (preferably on parchment) into rectangles of about 9”x14”. Place one rolled out sheet very carefully on top of the other and then roll starting with the longer side into a cylindrical log, similar to a swiss-roll. Smoothen it by rolling the log using the palm of your hand on the counter.

Cover tightly in plastic and refrigerate until firm (over-night). Slice and bake!

22 thoughts on “Checkerboard & Pinwheel Cookies
22 Replies

Leave a Reply