For some reason, I always make these cookies when I am stressed out. I made them in advance of my SAT so I would have something to snack on during breaks. I make them before I travel, so I always have something to munch on in my hotel room. They are just so comforting, not too sweet, and despite their intimidating appearance, they are not too difficult to form into perfect little checkerboard squares. Nonetheless, they are a very impressive and pretty cookie that will no doubt be welcome in your holiday cookie tins!

Checkerboard or Swirl Cookies

Adapted from Cookies from the Culinary Institute of America

Serves: about 3 dozen Checkerboard cookies or even more swirl cookies

Ingredients for Vanilla Dough: 

• ½ lb. butter, room temperature
• 1 cup confectioners’ sugar
• 1/3 cup granulated sugar
• 1 teaspoon salt
• 2 teaspoons vanilla extract
• 1 egg
• 2½ cups all-purpose flour

Ingredients for Chocolate Dough:

• ½ lb. butter, room temperature
• 1 cup confectioners’ sugar
• ½ cup granulated sugar
• 1 teaspoon salt
• 2 teaspoons vanilla extract
• 1 egg
• 2 cups all-purpose flour
• ½ cup cocoa powder

Directions:

1. Preheat oven to 350 degrees. In the bowl of a stand mixer, combine the butter and sugars on med-high speed until light and fluffy, about 4 minutes. Add salt, extract, and egg and mix until fully incorporated, stopping the mixer and scraping the sides as needed. Add the flour and mix until just combined. 
   1. For Checkerboard Cookies: Turn out dough onto a lightly floured surface and roll out the dough into a 6-inch square, about ½ inch high. Refrigerate while making the chocolate dough.
2. Second verse, same as the first. In the bowl of a stand mixer, combine the butter and sugars on med-high speed until light and fluffy, about 4 minutes. Add salt, extract, and egg and mix until fully incorporated, stopping the mixer and scraping the sides as needed. Whisk the flour and cocoa powder together in a small bowl. Add to the stand mixer and mix on low speed until just combined. 
   1. For Checkerboard Cookies: Pour dough out onto a lightly floured surface and roll out the dough into a 6-inch square, about ½ inch high. Refrigerate 30 minutes.
3. Checkerboard Cookies: Fill a small bowl with water and search around the kitchen cabinets for a pastry brush. Place the square of vanilla dough on a clean work surface. Brush with water. Top vanilla dough with the square of chocolate dough. Cut the dough squares in half to form two rectangles. Stack the rectangles on top of one another. You should have alternating layers of vanilla, chocolate, vanilla, chocolate. 
   1. Using a serrated knife, cut the dough into ½ inch thick slices. Assemble the blocks by stacking 4 slices, brushing with water between layers and alternating the colors to form a checkerboard pattern. At this point, refrigerate the dough for about 30 minutes. 
   1. You should have long blocks that look like a checkerboard. Slice the blocks ¼ inch thick and carefully place the sliced cookies on a parchment-lined baking sheet. 
   1. Bake 10-12 minutes, until very lightly golden brown. 
4. Swirl Cookies: Alternatively, divide the vanilla and the chocolate dough each into three equal pieces. Roll each piece into a rope. Place a chocolate rope on top of a vanilla rope and twist the two pieces together. Roll the dough into a log. Be careful, you still want to see a distinction between the vanilla and chocolate doughs.
   1. Fold the dough over on top of itself and roll into a log. Chill the dough until firm. Using a serrated knife, slice ¼ inch thick round cookies. 
   1. Repeat with other two vanilla and chocolate ropes. Bake cookies 8-10 minutes, until very lightly golden brown. 

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