Pinwheels and Checkerboards

Total Time

Prep: 30 min. + chilling Bake: 10 min./batch

Makes

6 dozen pinwheel and 4 dozen checkerboard cookies

Updated: Dec. 25, 2023
My mom used to make these cookies every Christmas, and I still love them. They are so colorful...and you can get two kinds of cookies from one dough! They're perfect for including in gift boxes.—Jill Heatwole, Pittsville, Maryland
Pinwheels and Checkerboards Recipe photo by Taste of Home

Ingredients

  • 1-1/4 cups butter, softened
  • 1 cup packed brown sugar
  • 1/2 cup sugar
  • 2 large eggs
  • 1/4 teaspoon vanilla extract
  • 4 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1 teaspoon salt
  • 1/4 teaspoon baking soda
  • Red and green gel food coloring
  • 1 ounce unsweetened chocolate, melted and cooled

Directions

  1. In a large bowl, cream butter and sugars until light and fluffy. Beat in eggs and vanilla. In another bowl, whisk flour, baking powder, salt and baking soda; gradually beat into creamed mixture.
  2. Divide dough into four portions. Tint one portion red and one portion green. Stir chocolate into another portion. Wrap chocolate and plain portions in plastic; refrigerate 1 hour or until easy to handle.
  3. For pinwheel cookies, divide red and green portions in half. Roll out each portion between waxed paper into a 9x6-in. rectangle. Refrigerate 30 minutes.
  4. Remove waxed paper. Place one green rectangle over a red rectangle. Roll up tightly jelly-roll style, starting with a long side; wrap in plastic. Repeat. Refrigerate 2 hours or until firm.
  5. For checkerboard cookies, divide plain and chocolate portions in half. Roll out each portion between waxed paper into a 6 4-in. rectangle. Cut each rectangle lengthwise into eight 1/2-in. strips.
  6. Stack the strips in groups of four, alternating plain and chocolate strips and forming eight separate stacks. Form a four-stack block by alternating chocolate-topped and plain-topped stacks. Repeat. Press together gently. Wrap in plastic. Refrigerate at least 2 hours.
  7. Preheat oven to 375°. Unwrap and cut pinwheel and checkerboard dough into 1/4-in. slices. Place 1 in. apart on ungreased baking sheets. Bake 9-11 minutes or until set. Remove to wire racks to cool.

Nutrition Facts

1 cookie: 45 calories, 2g fat (1g saturated fat), 8mg cholesterol, 43mg sodium, 6g carbohydrate (3g sugars, 0 fiber), 1g protein.