Chocolate Peppermint Pinwheel Cookies

  3.8 – 138 reviews  • Christmas Cookie
Level: Intermediate
Total: 2 hr 58 min
Prep: 45 min
Inactive: 2 hr
Cook: 13 min
Yield: 3 dozen cookies

Ingredients

  1. 1 batch Sugar Cookies, recipe follows
  2. 3 ounces unsweetened chocolate, melted
  3. 1 teaspoon vanilla extract
  4. 1 egg yolk
  5. 1 teaspoon peppermint extract
  6. 1/2 cup crushed candy canes or peppermint candies

Instructions

  1. Divide the dough in half and add chocolate and vanilla to 1 half and incorporate with hands. Add egg yolk, peppermint extract, and crushed candy to other half of dough and incorporate with hands. Cover both with plastic and chill for approximately 5 minutes. Roll out doughs separately to approximately 1/4-inch thickness. Place peppermint dough on top of chocolate and press together around the edges. Using waxed paper or flexible cutting board underneath, roll dough into log. Wrap in waxed paper and refrigerate for 2 hours.
  2. Preheat oven to 375 degrees F.
  3. Remove dough from the refrigerator and cut into 1/2-inch slices. Place cookies 1-inch apart on greased baking sheet, parchment, or silicone baking mat and bake for 12 to 13 minutes, rotating the pan halfway through cooking time. Remove from oven and let sit on baking sheet for 2 minutes, then move to a wire rack to cool completely. Store in an airtight container for up to 1 week.
  4. 3 cups all-purpose flour
  5. 3/4 teaspoon baking powder
  6. 1/4 teaspoon salt
  7. 1 cup unsalted butter, softened
  8. 1 cup sugar
  9. 1 egg, beaten
  10. 1 tablespoon milk
  11. Powdered sugar, for rolling out dough
  12. Sift together flour, baking powder, and salt. Set aside. Place butter and sugar in large bowl of electric stand mixer and beat until light in color. Add egg and milk and beat to combine. Put mixer on low speed, gradually add flour, and beat until mixture pulls away from the side of the bowl. Divide the dough in half, wrap in waxed paper, and refrigerate for 2 hours.

Nutrition Facts

Serving Size 1 of 36 servings
Calories 28
Total Fat 2 g
Saturated Fat 1 g
Carbohydrates 2 g
Dietary Fiber 1 g
Sugar 1 g
Protein 0 g
Cholesterol 4 mg
Sodium 1 mg

Reviews

Steven Russell
These were not worth the time and effort. I should’ve read the comments before I made them. I agree the chocolate part is a little dry and I did use 3 ounces of chocolate. More than that though is I’m a little disappointed in the lack of peppermint flavor I expected them to be much more flavorful.
Adam Jones
I’ve had this recipe saved for years and finally decided to try it this past Christmas for our family gathering. I have very little experience with dough cookies so I read all the comments and took everyone’s feedback into consideration. I mixed in the chocolate and peppermint into the 2 doughs w/o the initial 2 hour refrigeration as well. Patience is needed to fully incorporate the ingredients into the 2 doughs. I also found the chocolate dough to be drier than the peppermint dough when rolling out. I rolled it the long way as well and got almost 40 cookies. The candy cane melted, not sure why. Overall, this was very time consuming but the cookies turned out pretty good.
Christopher Stewart
Love these cookies! I’ve made them for many years. For those having issues with the chocolate dough, I found (from a previous reviewer) that if you add 1 tsp of oil to the melted chocolate, it won’t seize up once it hits the dough. Also, I mixed each dough 1/2 in the mixer, rolled into the log, and then put it in the fridge for 2 hours. Using the mixer definitely helps the chocolate get incorporated evenly and easily. These cookies do take time and patience but so worth it.
Colleen Evans
I’ve made these for years and they always come out perfect. For those saying the chocolate dough is too dry, be sure you’re using the correct amount of chocolate. Use 3 OUNCES, not 3 squares. Most baking chocolate comes in 4 oz bars. You need to use 3/4 of the bar. I can’t imagine why else it would be dry.

Nicholas Lynch
These cookies are a must have every year. I have tried different tweeks every year and I think I have arrived at the winning combination. Pulse the candy canes in a food processor. For the chocolate batch I used about 1/4 cup Hersheys Dark Cocoa, an egg yolk and 2 tbs of softened butter. This gave a much richer and darker color and a not as dry layer. I skipped the 2 hour chill and only refrigerated the dough for 5 minutes or so then rolled them out on silicone mats. Much easier to manuever than parchment. I roll them from the long end and got 3 Doz cookies. 
Joseph Perry
This was adopted as a tradition at our house 12 years ago. The additions to the basic dough can be done when initially making the dough BEFORE refrigerating. Then chill each dough separately. I roll mine on parchment paper, which makes placing the peppermint layer on top of the chocolate layer a cinch. The key to these cookies is to not over bake. Even after all this time I have to resist the urge to leave them longer. The bottoms should have just a hint of golden brown. This stage will give you a lightly crisp chocolate outside and a moist chewier center. The perfect mix of both crisp and chewy. While I love a crisp cookie, this  cookie is best baked as intended.
Timothy Wheeler
These cookies are lovely.
William Moyer
They are beautiful cookies, although I didn’t have trouble with the chocolate layer as others have mentioned. However, they are time intensive and while good, they aren’t great. A peppermint sugar cookie is easier and tastier. Love the trick of using an electric to cut the cookies, though.
Kelly Cruz
I really liked this recipe. I did add some vanilla to the sugar cookies dough but followed the recipe otherwise. I made one mistake of rolling the peppermint dough on the outside of the chocolate dough. Still tastes great but some of the candies melted away from the cookies as they baked so they don’t look as crisp and clean. 
Ariana Stewart
A new holiday tradition! This was an easy recipe to follow and while time consuming, well worth it! So many people have commented on these cookies!

 

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