Chocolate Peppermint Pinwheel Cookies

  3.9 – 155 reviews  • Christmas Cookie
Level: Intermediate
Total: 2 hr 58 min
Prep: 45 min
Inactive: 2 hr
Cook: 13 min
Yield: about 3 dozen

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
  7. 3 cups all-purpose flour
  8. 3/4 teaspoon baking powder
  9. 1/4 teaspoon salt
  10. 1 cup unsalted butter, softened
  11. 1 cup sugar
  12. 1 egg, beaten
  13. 1 tablespoon milk
  14. Powdered sugar, for rolling out dough

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 wax paper and refrigerate for 2 hours.
  2. Preheat oven to 375 degrees.
  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. 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.
  5. Preheat oven to 375 degrees F.
  6. Sprinkle surface where you will roll out dough with powdered sugar. Remove 1 wrapped pack of dough from refrigerator at a time, sprinkle rolling pin with powdered sugar, and roll out dough to 1/4-inch thick. Move the dough around and check underneath frequently to make sure it is not sticking. If dough has warmed during rolling, place cold cookie sheet on top for 10 minutes to chill. Cut into desired shape, place at least 1-inch apart on greased baking sheet, parchment, or silicone baking mat, and bake for 7 to 9 minutes or until cookies are just beginning to turn brown around the edges, rotating cookie sheet halfway through baking time. Let sit on baking sheet for 2 minutes after removal from oven and then move to complete cooling on wire rack. Serve as is or ice, as desired. Store in airtight container for up to 1 week.
  7. Yield: approximately 3 dozen, 2 1/2-inch cookies
  8. Prep Time: 15 minutes
  9. Cook Time: 7 to 9 minutes
  10. Inactive Prep Time: 2 hours

Nutrition Facts

Serving Size 1 of 36 servings
Calories 136
Total Fat 7 g
Saturated Fat 5 g
Carbohydrates 16 g
Dietary Fiber 1 g
Sugar 7 g
Protein 2 g
Cholesterol 22 mg
Sodium 28 mg

Reviews

Danielle Bailey
Excellent! We just finished eating one batch and are baking another. This is a definite keeper.
Bradley Brown
What a mess. Dough cracked and split so I was unable to make pinwheels. I rolled dough into rolls, stacked them. patted them into squarish cylinders, re refrigerated them and sliced for checkerboards. Taste was good!
Aaron Crawford
Have made these once before so I know that my family and I love the way these cookies taste, but they are CERTAINLY difficult to make! Last time as well as this time I had trouble with the chocolate dough, it was incredibly crumbly and difficult to work with.

I learned previously that if I were to fight through it the cookies would have crumbled away their outer chocolate layer, so this time I didn’t even try to roll out the chocolate dough! I rolled the peppermint out as the larger outer piece, and pressed the chocolate in my palms, then pieced the dough together onto the peppermint dough, pinched the edges together, and rolled it up that way.

I still had trouble rolling it (the chocolate split a piece of the dough right in the beginning), but they turned out pretty okay so far! I took someone’s advice from here in the reviews and I’ve got them in the freezer instead of the fridge, and am hopeful that cutting them will be easier because of it.

Overall difficult, but delicious!

David Vasquez
These cookies were okay, but not my favorite. They are very time consuming for the amount of flavor that they have. They are very pretty though. Use caution when baking them-the cookies on one of the cookie sheets were burnt on the bottom when I took them out. I think the peppermint pieces may have melted some and that sugar caused them to burn.
Richard Douglas
These are such a good use for sugar cookie dough. They take a dough that doesn’t have much of a taste and make it delicious
Madison Wright
I hate baking. But something about this one of year makes my heart clamor for cookies. Alton is a genius and for the past three years I’ve made his iced sugar cookies and they are always beautiful and delicious!! Well guess what, even with my limited baking skill, these cookies also turned out beautiful and delicious!!! My cookies came together beautifully and rolled like a dream. I did not experience the cracking other reviewers speak of, likely because I followed the recipe. My swirls turned out perfectly, perhaps even better than the ones Alton and Santa made!! For those who say these cookies taste like cardboard, perhaps their taste buds have been deadened by high fructose corn syrup and other wonderful synthetic delights that are sweeter than sugar. These cookies are delicious. End of story. The flavour balance is perfect, you get a rich deep chocolate taste that marries up perfectly with the sweetness of the peppermint layer. They are magic. Make them. Make them now.
Lisa Wilson
They were so good especially the melted candy cane pieces
Kimberly Pittman
Absolutely delicious cookies! There are quite a few steps in the recipe, but well worth the work. My son & I love Alton Brown & these cookies are almost as great as the man himself!!!
Craig Martinez
This is an awesome recipe, I have made them about a dozen times now. My family of 12 loves them, and the cookies sure disappear in a hurry. One thing I have found helpful is to go ahead and put an egg yolk into the chocolate dough half as well as the peppermint half. The chocolate rolls out better for me that way. Also, the cookies taste best after at least a day.
Robert Graham
This is our third year making these and they have become a family favorite! They are a bit time consuming but well worth the time spent. I agree with some of the other posters who suggest rolling the chocolate layer on the inside. They are just as pretty once they are cut with the peppermint on the outside.

 

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