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Pinwheels and Checkerboards

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
  • Total Time
    Prep: 30 min. + chilling Bake: 10 min./batch
  • Makes
    6 dozen pinwheel and 4 dozen checkerboard cookies

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

  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
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Reviews

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Average Rating:
  • Marianne
    Nov 25, 2019

    These were the most tasteless cookies I ever baked. Had various people taste them and they all stated they had no flavor. Can't understand how they won an award for these. Maybe because they look good. Don't waste your time making these.

  • Amanda
    Dec 20, 2017

    They're very cute cookies, but neither have very much flavor. I don't know if I'd add peppermint in the spirals like someone suggested, but that's because not everyone likes peppermint. I put these, along with snickerdoodles, in a tin as a Christmas gift for a coworker. I'm pleased with the way they look, but that's about all.

  • 2124arizona
    Jun 21, 2017

    The checkerboards are awesome, but the pinwheels are rather bland.

  • ms11145
    Nov 29, 2015

    I, too, have been making these cookies since I first saw the recipe. In fact, I HAVE to make these every Christmas. It's now a tradition. I failed at the checkerboards, so I just make the spirals. I also add mint flavoring (daughter's request). I have also made these for wedding showers using the bride's colors. Really pretty and I decorate by using colored sugar.

  • Kimberly Hines
    Aug 26, 2015

    These are so pretty and taste great. They really brighten up a cookie table or gift assortment. Sometimes I skip the chocolate checkered ones and make them all green and red because they take extra time to put together.

  • lvarner
    Sep 1, 2014

    These cookies do take some time to make, but they are so pretty for holiday parties and cookie exchanges. My grandmother used to make cookies similar to this, and I so loved them! The cookies have a nice, buttery flavor. I don't make them often but when I do make them, they really do make a special addition to the cookie tray or gift box!

  • dodit
    Dec 6, 2013

    i made these cookies several years ago. They are a special cookie to make at Christmas. just to comment on a few post i read. I liked the one about adding flavoring, since this is basically just a sugar cookie, and this is a time consuming recipe, especially the checkerboard one, but if you take your time, cut out the exact strips and line it all out right, they turn out really pretty. I got satisfaction in making these cookies. May try again this year. i had this copy of the magazine and lost it. it had a great homemade coconut creme pie recipe as well in it that i made at christmastime

  • aicenhour
    Jul 14, 2013

    We loved the way these turned out! They are so beautiful! I did use cake decorating color instead of the gel food coloring and they did fine. I didn't rate it 5 stars because we had a hard time with them. Difficulty level is pretty high to me. And the checkerboards were near impossible. All in all, we will make the pinwheels again, and perfect them :)

  • tahoeblue08
    Nov 29, 2012

    I have made these every year since first seeing the recipe. They are fun to make, look beautiful, and taste good, too!

  • NancyHanks
    Dec 10, 2011

    I've been making these for years. They are very time consuming, but worth doing just once a year (or twice... I did do a red, white and blue checkerboard version for the 4th).I think they taste great, too. I flavor some of the dough with almond extract and that way have 3 different tastes from one dough.I make one roll of the pinwheels with the green on the outside to get another look.