Checkered Flag Cookies Recipes

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.

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.

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!

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.

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:

• Make dough in a food processor: Combine the sugars, salt, and 1 1/2 cups (195 grams) of the flour in the work bowl. Add cold, diced butter and mix or pulse until it disappears, then keep running the machine until it just begins to clump. Add egg yolk (save the egg white for later) and vanilla and pulse until combined, then keep running the machine until one large or a few smaller smooth masses form. Make dough in a stand mixer or with a hand mixer: Combine butter, sugars, and salt in the bowl of your stand mixer and beat until creamy. If you began with cold butter in a stand mixer, this will take a couple minutes and require you to scrape down the bowl a few times. Once mixture is thoroughly combined, add egg yolk (save the egg white for later) and vanilla and beat until combined. Add 1 1/2 cups (195 grams) of the flour and beat until it disappears into a smooth dough. Both methods: Divide dough in half. [Each half will weigh 270 to 275 grams.] Leave one half in the mixing bowl or food processor. Add 1/4 cup (35 grams) remaining flour to it and pulse/mix until just combined. Scrape out the mixing bowl or food processor and scoop out this vanilla dough, setting it aside. Add the second half of the dough to the mixing bowl or food process and add the cocoa powder. Mix until evenly combined. This is now your chocolate dough. Heat oven: To 350°F (176°C) To checkerboard the doughs:Place each dough half between two pieces of parchment paper and roll each into (approximately) 4 to 5×10-inch (10 to 13×25-cm) rectangles that are 1/4-inch (6mm) thick. Slide both slabs of dough onto a cutting board or tray and freeze for 10 to 15 minutes, until firm like cold butter but not quite frozen solid.Remove the top piece of parchment from each slab (you can use these to line your baking sheet) and stack the chocolate and vanilla dough layers, pressing them gently together. Cut the slab in half the long way (i.e. forming two approximately 2×10-inch rectangles) and stack the halves, forming one long, striped slab. Press the layers gently, to adhere them, and return this to the freezer for another 10 to 15 minutes, or until it's very firm but not fully frozen.Remove this long slab from the freezer and, using your sharpest knife and steadiest hand, cut it the long way into eight 1/4-inch-wide slices. Arrange the first four into a checkerboarded log, flipping two of the slices over so the opposite flavor is on top. Repeat with second four into a second checkerboarded log. Wrap each in a piece of parchment paper and press it firmly into a long, squared-off log, adhering the layers. Return to the freezer for one last 10-minute stint, until solid to the touch. To finish cookies: Line a large baking sheet with parchment paper, or discarded parchment from your cookie slabs. Beat reserved egg white until just loosened. Gather your sanding sugar(s). Unwrap first checkerboarded log. Brush log with a thin coat of egg white and roll or sprinkle in sanding sugar. [Normal people choose one color per log. I cut each log into quarters and did each quarter in a different color.] Slice sugar-coated log into 1/4-inch-thick cookies, and arrange on prepared baking sheet with 1-inch space between them (they expand slightly). Repeat with second log, creating more cookies. Bake cookies: For 10 to 12 minutes, or until golden brown underneath. Let cookies rest on tray for 5 minutes, so they firm up a little, before transfer to a cooling rack to finish cooling and crisping up. Do ahead: Baked, cooled cookies keep for 3 weeks in a tin at room temperature. To spiral the doughs: Roll your chocolate and vanilla dough slabs each to 1/8-inch thick and stack them, patting them gently together. Chill in the freezer for just 5 to 10 minutes, until cold but not hard. Divide dough into two long, equal widths. With the vanilla dough underneath/forming the outer ring, roll each half of dough into a tight spiral. [I forgot and did the opposite, but always think it looks better with vanilla on the outside.] Wrap each spiral in parchment, pressing the dough into a firm log. Chill in freezer for 15 minutes, until solid but not frozen hard. Continue from "To finish cookies:" instructions above. To marble the doughs: Roll your chocolate and vanilla dough slabs each to 1/8-inch thick and stack them, patting them gently together. Cut into two stacked sections and squeeze each into a rough log, fold it over, and mash the log, kneading it once or twice. Press kneaded mounds together and form them back into a long log shape. Wrap tightly with parchment, pressing the dough into a firm log. Chill in freezer for 15 minutes, until solid but not frozen hard. Continue from "To finish cookies:" instructions above.