Peppermint Checkerboard Cookies

Voice of local TV newscaster… “Are the ingredients you use in holiday cookies, KILLING YOU? We’ll find out… but first, a snow leopard in Chicago gave birth to three cubs today, aren’t they cute? And now over to Jim in the weather center… Jim… it looks like there’s rain on the way.

Gosh, it's already day four of my Five Days of Cookies posts and since I grew up in a predominantly Italian family, you might think I should be posting about some true Italian classics like anise cookies or pizzelles. Anise cookies which are shaped like little wreaths and pizzelles which look like flattened waffle cones with an intricate design pressed into them. Both are made by the dozens and dozens each Christmas, a tradition passed from my grandmother to my mother. This tradition will most likely end with me. Eh, some traditions are overrated! If that is what you are expecting I am super sad to disappoint you. First off, I really don't like the taste of anise (think black licorice) so the anise cookies are off my "favorites list" right off the bat. As for pizzelles, well, you need a pizzelle iron to make those, and while I could borrow my mothers that really wouldn't help you in any way, would it? Plus, to be honest; I just don't have the patience to make pizzelles. With today's electric pizzelle irons you can make up to four cookies at a time but even at that rate pumping out five dozen cookies is too much work for me. My grandmothers pizzelle iron was the old fashioned kind, where you pressed the dough between two long handled, cast iron plates then held it over the stove, constantly flipping the iron over to keep each side hot until both sides of the cookie were cooked. Nope… that is not for me! My grandmother flavored her pizzelles with anise as well, so that's a second strike against them in my book. My grandfather must have really liked anise and that must be why my grandmother passed down these strongly anise-flavored recipes to my mother. He would also drink anisette shots too, sometimes after lighting them on fire. That also is a long held Italian tradition I don't have any desire to continue on my own. I suppose if you really like pizzelles you can message me and I'll send you my grandmothers recipe.

So... For today's cookie… A long time ago, I saw in my Christmas cookies cookbook, a peppermint candy cane cookie (which is where you intertwine one red rope of dough with one white rope of dough and shape into candy cane shapes). Instead of the candy cane shape though, which seemed like a lot of rolling and twisting, I decided I wanted to make a classic checkerboard pattern instead. It’s really not that hard, and you can make the dough and shape the cookie well in advance then just slice and bake them when you’re ready. Now mind you, I have nothing against candy canes or candy cane shaped cookies, I just wanted to do something different. I do think the checkerboard is a nice pattern for a cookie and they look good on a plate. I know the instructions seem long, but they are actually quite easy. Be prepared with a ruler as you’ll need it, and I used my stand mixer with the paddle attachment to make these but a regular hand held mixer and a large bowl will do just as well.


  • 1 cup unsalted butter, room temperature

  • 1 cup powdered sugar, sifted

  • ½ cup granulated sugar

  • 1 egg yolk

  • 1 egg

  • 1 teaspoon vanilla extract

  • ½ teaspoon peppermint extract

  • 2½ cups all-purpose flour

  • ½ teaspoon salt

  • ½ teaspoon red food coloring


In the bowl of your stand mixer beat the butter, powdered sugar, and granulated sugar on medium low speed until the butter is smooth, about 30 to 45 seconds or so, using the paddle attachment.

Add the egg yolk to the bowl and set the mixer on medium speed.

When the egg yolk has been incorporated add the whole egg with the mixer running and beat until fully incorporated.

Add the vanilla extract and mix to combine.

Add the flour and salt and with the mixer on low speed beat until the dough starts to come together in large clumps.

Remove ½ of the dough from the bowl (the easiest way is to remove all of the dough, weigh it, divide it in half and return one of the halves to the bowl). Be as accurate as you can be... it does matter.

Add the peppermint extract and the red food coloring to the bowl with the dough and beat on low or medium low speed to mix it together uniformly.

Shape each piece of dough into a rectangular shape, wrap in plastic wrap and refrigerate for at least 1 hour to firm up (preferable 2).

Now for the fun part:

First, note that this dough can become very sticky as it gets warm, so if it starts to warm up as your rolling or shaping, put it back in the fridge to get firm again.

Again, accuracy counts in the final look so grab a ruler you’re going to need it.

Cut each dough piece in half so you have two vanilla and two peppermint pieces (again, use your scale if you have one). When you are not working with a specific piece of dough return it to the refrigerator until you need it.

Now, take one piece of vanilla dough and roll it between two pieces of parchment paper into a 4½ by 4½ inch square. Make the sides as straight as possible and the corners as sharp as possible.  The dough will be about ½ inch thick. Return the dough to the refrigerator to firm up for at least 30 minutes.

Repeat with one portion of the peppermint dough.

When both pieces of rolled dough have firmed back up, again working with one piece at a time and using your ruler to measure, cut the two squares into ½ inch strips. In the end, you will have 9 white and 9 red strips measuring 4½ inches long and ½ inch wide.

Place three strips, alternating colors next to each other gently pressing them together. If the dough does not stick to itself you can brush a little bit of water between the pieces to help “glue” them together.

For the second row alternate the colors so that red is on white and white is on red, then do the same for the third row. Press the layers together gently so as not to change the shape but to be sure they adhere to each other. Replace the block in the refrigerator for at least 1 hour to chill.

Make the second block the same way noting that you’ll start the first row of your second block opposite of the way you started the first block.

While the blocks are getting firm again:

Take out one of the remaining dough pieces and roll the dough between two pieces of parchment paper into a rectangle that is at least 4½ inches wide and at least 7 inches long. The dough will be about a little more than ⅛ inch thick. Return the dough to the refrigerator and repeat with the remaining piece of dough.

When everything is thoroughly chilled wrap each block with the flat dough in a single layer trimming off the ends and extra dough as needed. Again, brush the dough with a little water to help stick the pieces together… but just a little ok?

Tip: It is easier to make your seam on the flat part of the block rather than the corner.

Once again… and I promise this is the last time. Wrap the completed blocks of dough in plastic wrap and return to the refrigerator and chill at least 30 minutes (the colder the dough is when they bake, the less they will spread).

Preheat the oven to 350°F with the rack in the center position.

Take out one cookie block and using a sharp knife, slice the block into ¼ inch squares.

Arrange on a parchment lined baking sheet spacing at least ½ inch apart.

Bake for 12 minutes to 13 minutes or until the edges just barely start to turn golden.

Cool on a wire rack and then store in an airtight container.


I really like these cookies, I hope you like them as well. And remember that if you don't want to take the time to measure and stack and slice these, you can always revert to the candy cane shape and simply roll two different colored balls of dough into 5 inch ropes then twist them together.