Peppermint Fudge Pinwheels

Christmas is my favorite time of year and one of the main reasons for that is all the baking I get to do. Even when I didn’t cook much, I’ve always liked to bake and cookies are just about my favorite thing to make. Plus this time of year is the only time besides my birthday and Thanksgiving that I let myself make/eat whatever I want and I don’t feel guilty about it. Diets are what January is for. (I’ve already signed up for Recipe Girl’s Ten in ’10 challenge!) So expect a bunch of sweet recipes around here for the next few weeks because I’m in the baking mood.

I’m obviously obsessed with black and white desserts, so I knew I had to make these as soon as I saw them. The original recipe isn’t very christmas-y, but that was easily remedied with the addition of some peppermint extract to the chocolate cookie dough AND to the fudge frosting in the middle. Don’t worry though, these cookies aren’t crazy peppermint-y. The vanilla part of the cookie balances out the peppermint and makes it much more subtle.

Peppermint Fudge Pinwheels

The cookie part is thick, it’s very much like a shortbread (these don’t rise at all). I made a note about thickness in the directions below. You should slice them thinner if you want a crispier cookie, but they also burn more easily, so you’ll have to watch them closely when baking. I made mine kind of thick, which is how I like them. They also don’t have to be made into sandwiches, but I thought they were a bit plain without the fudge in the middle. The fudge filling is pretty much the exact consistency of the filling of an oreo.

The only downside to these cookies are that you have to refrigerate the dough for 9 hours. Who wants to wait that long for cookies?? They are worth the wait, though. The recipe is super easy to mix up, and rolling everything out isn’t too complicated, so you could make this after dinner, refrigerate the dough roll overnight and slice and bake the next day. Or you could even freeze the dough roll and take it out whenever you are ready to bake. I actually thought these tasted better the day after I baked them, so if you can wait 2 days (I couldn’t) these are quite the treat. These would be great cookies to take to a party or give as a gift because they are so pretty and they keep well.

If peppermint isn’t your thing I bet these would be really good with orange extract instead. Or of course you could just use plain vanilla, but I think they’d be a bit bland if there wasn’t any kind of flavoring.

Peppermint Fudge Pinwheels

Peppermint Fudge Pinwheels

adapted from Betty Crocker’s Cookbook

Cookies | Servings: 4 dozen
Prep time: 30 min | Cook time: 1 hour | Total time: 1 hour 30 min

Ingredients

  • 1 1/4 cups unsalted butter, softened
  • 1 1/2 cups powdered sugar
  • 1 egg
  • 1 tsp. vanilla
  • 3 cups cake flour (all purpose is fine if you don’t have cake flour)
  • 1/4 tsp. salt
  • 1/4 cup cocoa
  • 1 tsp. peppermint extract

Peppermint Fudge Filling

  • 1/4 cup shortening
  • 1/3 cup milk
  • 1 cup sugar
  • 3 oz. bittersweet/unsweet chocolate
  • 1/4 tsp. salt
  • 1/2 tsp. peppermint extract

Process

  1. In a large bowl, cream together butter and sugar. Beat in egg and vanilla.
  2. Mix in flour and salt.
  3. Remove half the dough, wrap in plastic or wax paper. Place in refrigerator to chill.
  4. Mix cocoa and peppermint extract into the remaining dough. Wrap in plastic or wax paper. Place in refrigerator to chill with vanilla dough for 1 hour.
  5. On a lightly floured piece of wax paper, roll vanilla dough into a 13×9 inch rectangle about 3/16 inch thick. Carefully lift the wax paper and put it on a cookie sheet. Chill in the freezer or fridge for a few minutes. (You don’t have to do this, but I think freezing it for a few minutes makes it easier to roll up.)
  6. Meanwhile, on a lightly floured piece of wax paper roll out the chocolate dough into a 13×8 inch rectangle about 3/16 inch thick. Chill for a couple minutes if necessary.
  7. Place vanilla dough on the counter, carefully flip over the chocolate dough and lay it flat on top of the vanilla dough, leaving about 1/4 inch gap on the right side. Peel the wax paper off the chocolate dough. Trim edges so that they are smooth and even on all sides.
  8. Starting from the right side, carefully roll up the dough. If it starts to crack, unroll and let warm up for a minute, then continue rolling up tightly into a long roll/log. Wrap in plastic or wax paper and refrigerate for 8 hours.
  9. Preheat oven to 400 degrees (F). Cut roll into slices about 1/8 inch thick* and place each slice on a parchment/silpat lined cookie sheet about 1 inch apart. Bake for 6-8 minutes or until they start to brown around the edges. Immediately remove from pan and place on cooling rack.

    *Note: These cookies don’t rise at all, so the thickness you cut is as thick as they get. I cut mine a bit thicker because I noticed the thinner ones were burning around the edges more easily. But since they are sandwich cookies, you don’t want them to be too thick (definitely keep them 1/4″ or less). If you prefer a crispier cookie (I don’t), you may want to cut them 1/8″ and just watch them really carefully while baking so that you can take them out as soon as they start browning.

  10. While the cookies are cooling, start the filling: Melt shortening and chocolate in a small pan over medium-low heat.
  11. Add in milk, sugar and salt.
  12. Heat to a rolling boil, stirring occasionally. Boil 1 minute without stirring.
  13. Place pan in a bowl of ice water and beat until frosting is thick. Stir in peppermint extract.
  14. Spread frosting on the inside of a cookie and press another cookie on top to make a sandwich.