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Word Game and Checkers Cookies

These board-game-themed sugar cookies are the perfect dessert for your next game night. For the "word game" pieces, we cut out fifty-two squares from plain cookie dough and two of each letter from chocolate dough. For checkers, we cut both doughs into rounds.

  • Yield: Makes 52 word-game squares and about 3 dozen checkers

Photography: Unknown

Source: Martha Stewart Living, January 2003


  • 1 cup (2 sticks) unsalted butter, softened
  • 2 cups sugar
  • 2 large eggs
  • 2 teaspoons pure vanilla extract
  • 4 cups sifted all-purpose flour, plus more for work surface and cookie cutters
  • 1 teaspoon baking powder
  • 1/2 teaspoon salt
  • 1/4 cup unsweetened cocoa powder


  1. In the bowl of an electric mixer fitted with the paddle attachment, cream butter and sugar until light and fluffy, about 2 minutes. Add eggs and vanilla; beat until thoroughly combined. Beat in 2 cups flour, baking powder, and salt.

  2. Divide dough in half; transfer one half to another bowl. To the remaining half in mixer bowl, add 1 1/4 cups flour; beat until combined. Transfer to a piece of plastic wrap. Return other dough half to mixer bowl; add cocoa powder and remaining 3/4 cup flour. Beat until combined. Transfer to another piece of plastic wrap. Flatten both halves into disks, and wrap well. Chill at least 30 minutes or overnight.

  3. Turn out plain dough onto a lightly floured surface; divide in half. Roll out one half about 1/8 inch thick. Using a paring knife or cookie cutter, cut dough into 1 1/2-inch squares; arrange on a parchment-lined baking sheet. Roll out other dough half; cut just enough additional squares to total 52. Place on baking sheet; chill until firm, at least 20 minutes.

  4. Meanwhile, using a 1 1/4-inch cookie cutter, cut out rounds from remaining plain dough. Place on a parchment-lined baking sheet; chill until firm.

  5. Remove chocolate dough from the refrigerator, and divide in half. Roll out one half about 1/8 inch thick. Using cookie cutters, cut out 2 of each letter (for a total of 52 letters), and place on a parchment-lined baking sheet; dip the cookie cutters in flour before each cut, then gently tap the side of the cutter against the counter or your hand to remove the letter.

  6. Using the same cookie cutter, cut out additional rounds from remaining chocolate dough; place on baking sheet with plain rounds. Chill until firm.

  7. Preheat oven to 350 degrees. Remove squares and letters from refrigerator. Using a pastry brush or your fingertip, dampen the top of each square with water; center a letter on top of each square. Bake until just starting to brown, 9 to 10 minutes, rotating baking sheets halfway through cooking time. Transfer cookies to wire racks to cool completely.

  8. Remove rounds from refrigerator, and bake until just starting to brown and turn crisp, 9 to 10 minutes. Transfer cookies to wire racks to cool. Cookies can be stored in airtight containers at room temperature up to 5 days.


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