Chocolate Orange Pinwheels and Checkerboard Cookies

  • Post category:Christmas / Sweets
  • Post author:
  • Post last modified:January 30, 2023

Christmas baking has begun and I love this time of year! It’s a time to start making those special baked goods everyone enjoys each year to create memories with love ones. I started with the Chocolate Pinwheels and Checkerboard cookies, one of my favorites!!  

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This recipe requires some time and effort, but it is well worth it once you have it as part of your cookie collection. They really stand out on a cookie tray visually and the flavours are decadent. By adding the orange zest with the chocolate makes these cookies absolutely delicious. Simple add orange zest to half of the dough.  

When making these cookies

Melting the chocolate can be done by using a double boiler or placing a stainless steel bowl over a pot with water added and these methods will avoid the chocolate from burning. If you melt the chocolate in a microwave, set it at 30-40 seconds, but keep checking every 10 seconds and stir the chocolate until it is melted. 

Best way to divide the dough equally is by using a scale and weigh each portion. 

Avoid overmixing the dough, remember these are cookies. Refrigerate for 45-60 minutes for easier handling when making the pinwheels and checkerboard designs. 

Once the pinwheels and checkerboard designs are rolled and created,  wrap and refrigerate for one hour. 

Recipe ingredients:

  • flour: I used organic all-purpose flour, however it isn’t necessary
  • baking powder
  • satl
  • dark chocolate
  • unsalted butter
  • sugar; my preference is raw fine sugar
  • pure vanilla extract
  • cocoa powder
  • orange zest 
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Chocolate Orange Pinwheels and Checkerboards

Rose
Chocolate and vanilla flavour combination makes these cookies irresistible. These cookies are a perfect Christmas cookie, slightly dense with some crunch.
4 from 1 vote
Prep Time 10 minutes
Refrigeration time 1 hour 45 minutes
Total Time 2 hours 5 minutes
Course Dessert
Servings 50 cookies
Calories 72 kcal

Equipment

  • Baking sheet
  • double boiler
  • stand mixer or hand-held mixer

Ingredients
  

  • 2 cups organic all-purpose flour
  • 1/2 tsp baking powder
  • 1/4 tsp salt
  • 2 oz dark chocolate/semisweet chocolate
  • 1 cup unsalted butter, room temperature
  • 3/4 cup raw fine sugar
  • 2 eggs, separated
  • 2 tsp pure vanilla extract
  • 1 tbsp cocoa powder
  • 2 tsp grated orange zest

Instructions
 

  • In a medium bowl, sift together the flour, baking powder and salt. Set aside.
  • Place chocolate in the top of a double boiler over steaming water. Stir until the chocolate has melted and set aside to cool.
  • In a large bowl, beat with stand mixer or hand held mixer butter and sugar at medium speed until smooth, about 3 minutes. Add the two egg yolks and vanilla, beat at low speed just until blended.
  • Add the dry ingredients and mix just until incorporated and dough is smooth. The longer you beat the dough, the softer it gets and becomes more difficult to handle.
  • Divide the dough in half. Put one-half of the dough in a separate bowl and stir in the orange zest. The dough remaining in the mixing bowl, add the melted chocolate and cocoa powder. Mix with a wooden spoon or low-speed just until the chocolate has blended completely into the dough.
  • Form each dough into a disc and wrap separately in plastic wrap or wax paper and refrigerate for about 45-60 minutes.
  • Two options: pinwheels or checkerboards or both.

Pinwheel cookies:

  • Remove dough from refrigerator. Take each dough disc and place between two sheets of wax paper and roll out into a rectangle to about 1/8 inch thickness.
  • Remove the top piece of wax paper from each rectangle. Carefully, take the chocolate rectangle and flip onto the other dough rectangle. Trim the edges evenly and roll lengthwise. Gently press in the ends and trim evenly. The roll should be approximately 9 inches long.
    Wrap in plastic wrap and refrigerator for 1 hour or overnight.

Checkerboard cookies:

  • Remove dough from refrigerator and cut each disc into 6 equal portions. Take each strip/portion and begin to roll in your hand and then continue on the counter with a little
    bit of flour to prevent dough from sticking. Roll out each approximately 9 inches long.
  • Begin forming the checkerboard by placing each roll alternating each dough. At this time, slightly beat the egg white and lightly brush the top of each layer with your finger with the egg white. This will help each layer to glue together. Gently press the layers closely together to create a checkerboard pattern.
  • Trim the end evenly. Wrap in plastic wrap and refrigerator for 1 hour or overnight
  • Preheat oven to 350 °F. Line baking sheets with parchment paper.
  • Using a sharp knife, cut either pinwheel or checkerboard log crosswise into 3/8 inch slices. Place 1-2 inch apart on the prepared baking sheets.
  • Bake cookies about 8-12 minutes or just until the edges begin to turn lightly golden.
  • Allow cookies to cool on wire racks. Store in an air tight container or freezer up to 2 months.

Nutrition

Calories: 72kcalCarbohydrates: 7gProtein: 1gFat: 4gSaturated Fat: 3gTrans Fat: 1gCholesterol: 16mgSodium: 19mgPotassium: 19mgFiber: 1gSugar: 3gVitamin A: 124IUCalcium: 6mgIron: 1mg
Tried this recipe?Let us know how it was!

How to make Pinwheel cookies

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Once you mix the ingredients together, divide the dough in half and add the chocolate, wrap each dough separately and refrigerate. Once they have been in the refrigerator for 45-60 minutes, and if you are making pinwheels and checkerboard cookies, divide the each dough in half. Roll out half of each dough to create the pinwheels. 

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Carefully lay the chocolate over the regular vanilla dough and trim edges evenly and begin to roll in a jellyroll fashion. Tuck in the ends and make sure the roll is tight enough that is doesn’t come apart. 

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Cut the roll approximately 3/8 inch thickness. That thickness will create a little more a thicker cookie, rather then a thin cookie. Place the cookies about 2 inches apart on the lined baking sheet with parchment paper. 

How to make Checkerboard cookies

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Divide each dough into 6 sections to create 12 rolls in total. Add a small amount of flour to your hand or counter to avoid the dough sticking and start rolling each section. When placing the rolls next to each other, alternate the chocolate with the vanilla, and add a little bit of egg white to seal the rolls together and make sure you place them close enough together so they will bake into each other.   

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Cut the roll into 3/8 inch wide pieces. Important to note: once the dough sits out at room temperature, the dough begins to warm, and will bake faster than the first batch, probably at least 5 minutes sooner. That’s way you may notice my checkerboard cookies are a little more toasty than the pinwheels. 🙂

Enjoy these decorative cookies during the holiday season. They sure decorate a plater of cookies and they will definitely impress your family and guests. 

This Post Has 2 Comments

  1. Janine

    4 stars
    Great cookies, but I didn’t know when to put the orange zest in. In addition, I didn’t know if only one egg was divided or both. Please specify.

    1. admin

      Hi Janine,
      They really are great cookies! I apologize, the 2 egg yolks are added at the same time with the vanilla once the butter and sugar are beaten until smooth. Once the dough is divided, the orange zest is added to the one-half of the dough and the other half the melted chocolate and cocoa powder is added.
      Hope this helps…if you have any questions, please feel free to email me.

4 from 1 vote

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