Best Checkered Flag Cookies Recipes

CHECKERBOARD COOKIES

Steps:

• Whisk to combine the flour, baking powder, and salt. Set aside.
• In a stand mixer bowl fitted with the paddle attachment, beat the butter to spread around the bowl. With the mixer running, stream in the sugar. Review my creaming article if you have forgotten how to do this properly. Add the egg and vanilla, and mix until combined.
• Slowly add the flour mixture to the stand mixer bowl until combined.
• Remove half of the dough, wrap in plastic and put into the fridge.
• Add the espresso powder, chocolate, and cocoa powder to the remaining dough, and mix to combine.
• Remove the coffee dough from the mixer and shape into a squared off block, about 2 inches tall and wide, and 6 inches long. Do the same with the vanilla dough.
• Refrigerate both doughs on a sheet pan for 1 hour.
• Cut each block into desired size for checkering. I cut the block into thirds, then into thirds again (see blog photos).
• Start alternating the pieces with chocolate and vanilla, then square it off and press together. Refrigerate the dough for 30 minutes.
• Preheat the oven to 350 degrees F. Cut the dough into 1/4 inch thick slices and place on a parchment paper lined sheet pan.
• Bake for 10 minutes, then cool on a wire rack. Enjoy!

CHECKERBOARD COOKIES

Steps:

• In the bowl of your stand mixer fitted with the paddle attachment mix together the butter and sugar for 2 minutes.
• Add in the egg, the yolk, vanilla, baking powder, and salt and mix for 1 minute until smooth, scraping the sides of the bowl as necessary.
• Turn the mixer to low and add in the flour, mixing until just combined.
• Divide the dough in half, removing half from the mixing bowl.
• Add in the cocoa powder to the remaining dough in the mixing bowl and mix until incorporated.
• Form each dough into a squared off log, 2- inches tall and 6- inches long. Make sure both are the same size.
• Place dough on a baking sheet and cover with cling wrap. Place dough into the refrigerator to chill for at least 1 hour.
• Using a sharp knife slice the dough into thirds, longwise. Then turn the dough one turn and cut into thirds again. You will have 9 strips. Repeat the process with the other dough. You will have 18 strips total.
• Lay 1 piece of vanilla dough, one piece of chocolate, and another piece of vanilla on a flat surface next to each other. Top the 3 strips with alternating colors. Repeat this once more, so you have a square log. Press the dough strips together tightly, keeping the square shape. Repeat this with the remaining dough.
• Refrigerate again for at least 30 minutes.
• Preheat the oven to 350°F. Line a baking sheet with Reynolds Kitchens® Parchment Paper.
• Remove the dough from the refrigerator and slice into 1/4- inch pieces.
• Place the pieces on the prepared baking sheet.
• Bake for 9-10 minutes, or until set. Transfer to a wire rack to cool completely.

RED AND WHITE CHECKERBOARD COOKIES

Steps:

• Put the white chocolate in a microwave-safe bowl and microwave in 30-second intervals, stirring, until melted. Let cool slightly.
• Beat the butter, granulated sugar and salt in a large bowl with a mixer on medium speed until creamy, 2 to 3 minutes. Beat in the egg and vanilla, then mix in the melted white chocolate. Reduce the speed to low and mix in the flour in two batches until just combined.
• Remove half of the dough; beat the orange zest and food coloring into the remaining dough. Wrap the plain dough and red dough separately in plastic wrap, flatten each into a rectangle and chill until firm, at least 1 hour.
• Working on 2 separate sheets of floured parchment, roll out each piece of dough into a rough 5-by-10-inch rectangle (about 3/8 inch thick), then trim each piece to form a 4 1/2-by-9 1/2-inch rectangle. Using a sharp knife, cut each rectangle lengthwise into nine 1/2-inch-wide strips. (If the dough gets too soft, refrigerate until firm.)
• Lay 3 alternating color strips together (white-red-white). Using a wet finger, moisten the sides and tops so the strips adhere without gaps, pressing to seal. Top with 3 strips in the opposite pattern (red-white-red). Top with 3 more strips, repeating the first pattern. Repeat to build another log, starting with a red-white-red pattern. Wrap the logs and chill for 2 hours.
• Position racks in the upper and lower thirds of the oven and preheat to 350˚ F. Line 3 baking sheets with parchment. Unwrap the dough. Lightly brush the logs with water, then firmly press the sides in the sanding sugar. Using a sharp knife, trim the ends of the logs, then slice into 1/3- to 1/2-inch-thick cookies, about 24 per log.
• Arrange the cookies 1 1/2 inches apart on the baking sheets. Bake 2 of the pans (refrigerate the other), switching positions halfway through, until the cookies are just set but not browned, 12 to 15 minutes. Let cool 5 minutes on the pans, then remove to a rack to cool completely. Repeat with the remaining baking sheet.

CHECKERBOARD COOKIES

Steps:

• Cream butter and sugar. Add vanilla. Add flour and salt and blend well. Divide dough in half. Add cocoa to 1/2 of dough. Let rest. Roll 1/4 inch cylinders of chocolate and plain vanilla dough about 12 inches long. Arrange in checkerboard by alternating 6 cylinders of chocolate and vanilla dough, contrasting each time to six layers total. Press tightly. Wrap in plastic wrap and chill at least 1/2 hour.
• Preheat oven to 350 degrees. With a sharp knife, slice the dough into rounds about 1/3-inch thick. Place 1 inch apart on a parchment covered baking sheet. Bake for about 10 minutes or until lightly golden.

CHOCOLATE AND VANILLA CHECKERED FLAG CAKE

Steps:

• For the vanilla and chocolate cakes: Preheat the oven to 350 degrees F. Prepare four 9-inch cake pans with the nonstick cooking spray and dust with flour.
• In a stand mixer fitted with a whisk attachment, add the granulated sugar and butter and cream together until combined, about 2 minutes. Add the eggs one at a time, beating to incorporate them. Add the baking powder, salt and 1 cup of the flour and continue to beat. Add the milk and remaining 2 cups flour, alternating back and forth. And the vanilla extract and beat for 1 more minute. Pour half of the batter into 2 of the prepared cake pans, reserving half to make into chocolate cake batter.
• To make the chocolate batter, add the cocoa and hot water to a small bowl and mix to make a paste. Combine the chocolate paste with the remaining cake batter and mix until evenly combined. Pour the chocolate cake batter into the remaining 2 cake pans.
• Place all 4 cake pans in the oven and bake until a toothpick inserted in the center of each comes out clean, 30 to 35 minutes. Let cool on a wire baking rack for 30 minutes.
• For the vanilla frosting: In the bowl of a stand mixer fitted with a whisk attachment, add the confectioners' sugar and butter and mix on low speed for 1 minute until combined, then increase the speed to medium and beat until fluffy, another 3 minutes. Add the heavy cream and vanilla bean seeds and continue to beat for 1 more minute. Set aside.
• To assemble checkerboard cake: To each cake, using a 5.5-inch round cookie cutter, cut out 1 ring, place a 2.5-inch round cookie cutter on the inside of the 5.5-inch ring to cut out a 2nd round. Repeat with the other 3 cakes. (This will give you 2 rings and 1 round per cake)
• For the first layer: Place the largest yellow cake ring on your desired cake plate, place the second largest chocolate cake ring inside of the yellow cake ring, then place the smallest yellow cake round inside of the chocolate cake ring. Spread an even layer of vanilla frosting on top.
• For the second layer: Place the largest chocolate cake ring on top of the first frosted layer of cake, place the second largest yellow cake ring inside of the of the chocolate ring, then place the smallest chocolate round inside of the yellow cake ring. Spread an even layer of vanilla frosting on top.
• For the third and fourth layers, repeat the steps for the first 2 layers. Finish the top of the cake with an even layer of frosting, leaving the sides of the cake untouched.

CHECKERBOARD COOKIES

Steps:

• In the bowl of an electric mixer fitted with the paddle attachment, cream butter and sugar until well blended, 1 to 2 minutes. Add vanilla extract, lemon extract, and salt. With mixer on low speed, gradually add flour, scraping down sides of bowl.
• Turn dough out onto a clean work surface; it will be loose and crumbly. Knead dough by pushing small amounts away from you with the heel of your hand for 1 to 2 minutes. Divide dough in half. Sprinkle cocoa powder over one of the halves. Knead until cocoa has been fully incorporated.
• Place each half of the kneaded dough between 2 sheets of plastic. Using a rolling pin, shape dough into two 7-inch squares, about 3/8 inch thick. Using a sharp knife and a ruler, slice each square into nine 3/4-inch-wide strips.
• Whisk together the egg and 1 tablespoon water. Cover work surface with plastic wrap. Place 3 strips of dough on plastic, alternating white and chocolate strips. Brush tops and in between the strips with egg wash. Gently press strips together. Repeat, forming second and third layers, alternating colors to create a checkerboard effect. Wrap assembled log in plastic. Repeat process for second log, reversing color pattern. Refrigerate 30 minutes, or freeze 15 minutes.
• Preheat oven to 350 degrees. Line a baking sheet with a Silpat baking mat or parchment paper. Slice each log into 1/4-inch-thick slices; place on baking sheet. Bake until done, 10 to 12 minutes. Remove baking sheet from oven, and let cookies cool 2 minutes. Transfer cookies to a wire rack to cool completely.

SUGAR STAR & FLAG COOKIES

Steps:

• In a large bowl, cream the butter, cream cheese and sugar until light and fluffy. Beat in eggs and extracts. Combine the flour, baking powder and salt; gradually add to creamed mixture and mix well. Cover and refrigerate for 2 hours or until easy to handle., On a lightly floured surface, roll out dough to 1/4-in. thickness. Cut with floured 2- to 3-in. cookie cutters. Place 1 in. apart on ungreased baking sheets. Sprinkle with colored sugars as desired., Bake at 350° for 9-11 minutes or until set. Cool for 2 minutes before removing from pans to wire racks to cool completely. Decorate with icing and additional sugars if desired.