Chocolate Peppermint Pinwheel Cookies

Chocolate Peppermint Pinwheel Cookies are the perfect cookie to share during the holidays! If you dream about the combination of peppermint and chocolate together during the holidays, these pretty swirled cookies will be your new favorite Christmas cookie!

When I think of the Christmas season, I think of peppermint. From candy canes to cookies, I'll take it all.

Usually, I am not a huge fan of chocolate and peppermint together, but I wanted to try to come up with a recipe that I would like that had a good balance of chocolate and peppermint.

And that's how I dreamed up these Christmas pinwheel cookies!

Chocolate Peppermint Pinwheel Cookies Recipe

These pretty swirl cookies are made with two sheets of cookie dough.

One is smooth and chocolatey, and the other is infused with white chocolate, peppermint and candy cane pieces.

They're layered on top of each other and then rolled up together into a log.

The log is then sliced to create beautiful, festive pinwheel cookie slices with colorful swirls of the perfect balance of flavor.

They taste like peppermint bark, but in cookie form!

Soft and crispy Christmas Pinwheel Cookies

My favorite part about these Chocolate Peppermint Pinwheel Cookies isn't even the flavor.

The two layers are rolled together so the chocolate outside layer gets crispy while the inner peppermint layer stays soft.

If you've ever had an internal debate about soft versus crispy cookies, these chocolate peppermint pinwheel cookies are the answer!

Holiday Pinwheel Cookies: A long recipe, but it's worth it

I'm going to be straight with you. This is not a simple recipe.

Holiday Pinwheel Cookies will be well worth a Spiked Peppermint Hot Chocolate at the end of the day.

If you have some time and want to try a more complicated cookie recipe, you may wish to try these pinwheel cookies.

Because the cookie dough does need time to chill (three times, in fact), these may not be the ideal cookie to make if you're the one hosting and cooking ALL the other food.

If that sounds like you, then you might want to try my 6-ingredient peppermint crinkle cookies.

But if you're attending a party or visiting family for the holidays, these are the perfect treat to bring! I promise they are worth it.

And you can multi-task while the dough chills in the fridge!

How to make Peppermint Chocolate Pinwheel Cookies

Let's walk through how to make these Christmas pinwheel cookies. It seems complicated because it's a lot of steps, but I know you can do it!

Make the dough

First, you'll cream together the butter and sugar using a stand mixer or handheld mixer. It's a lot of mixing, but you can do it by hand, too.

Once combined, add the egg and ½ teaspoon vanilla extract.

Split the dough into two bowls. (You can use a kitchen scale if you want to be precise, but eye-balling it is okay, too!)

Chocolate dough

In the first bowl, we'll make the chocolate dough.

Add cocoa powder and 1 teaspoon vanilla.

In a microwave-safe bowl, melt chocolate chips. Melt for 30 seconds, then stir. Continue melting in 15-second intervals until melted completely. Do not burn!

While melted chocolate is still warm, add to the chocolate dough until combined.

Shape dough with hands into a roughly-shaped rectangle on top of plastic wrap. Wrap it up and set it aside.

Peppermint dough

In a second bowl, add candy cane pieces, peppermint extract and melted white chocolate chips. (Repeat steps for melting chocolate chips above. White chocolate will melt faster.)

Shape peppermint dough with hands into a roughly-shaped rectangle on top of plastic wrap. Wrap it up well!

Place both sets of wrapped dough on a cookie sheet and chill in the refrigerator for 30 minutes.

Make the logs

Remove dough from the fridge and plastic wrap and place each ball of dough onto a large sheet of wax paper.

Place another sheet of wax paper on top of the dough — this will keep it from sticking to the rolling pin. Use a rolling pin to roll the dough into a rectangle about an inch thick.

Repeat with the second set of dough, trying to keep the shapes of the two as similar as possible.

Without removing the waxed paper, layer the dough on a baking sheet and refrigerate for 1 hour. This will make it easier to roll into the swirled pinwheel shape.

Remove the dough from the fridge and peel off the top layer of wax paper from each.

Invert the peppermint on top of the chocolate dough, aligning the two layers as closely as possible. Use your rolling pin to gently seal the two layers together by rolling over the top layer.

Peel off the top layer of wax paper. Start with the edge of the dough closest to you and roll the edge of the dough over so there is no gap in the center of the pinwheel.

Use the wax paper to help continue rolling the dough into a tight cylinder. You want to try to keep the log as compact as possible.

Wrap the rolled log in another piece of plastic wrap and refrigerate for another 1-2 hours. This is the last chill time, I promise! But you don't want to skip this step so the log will slice beautifully.

Bake the cookies

First, preheat your oven to 350°F. You can line a baking sheet with parchment paper or a silicone baking mat, but I've never had a problem with baking them right on my cookie sheet.

Remove from the fridge and use a sharp knife to cut pinwheels that are about ¾-inch thick.

Place on the baking sheets, spacing them 1 inch apart, and bake for 12-14 minutes. Cookies will expand just a little bit.

Let the cookies rest on the baking sheet for a minute, then move them to a wire cooling rack (while cookies are still warm) to cool.

Variations

There are a few ways you can make these cookies your own:

• Add ¼ cup of red and green sprinkles to the vanilla cookie mixture when you add the peppermint candies.
• Add 6-8 drops of red food coloring to the vanilla cookie dough (after you've removed half for the chocolate).
• At the end of creating the chocolate dough, stir in ½ cup of mini chocolate chips or mini M&M's for more chocolate flavor.
• Dip the cookies in white or dark chocolate and roll in extra crushed candy canes for more chocolate peppermint flavor.
• Use different color candy canes for fun pops of color.

Tips for Making Pinweel Cookies Stress-Free & Easy

As I mentioned before, the process for these cookies can be a little hands-on and time-intensive.

Mostly that is due to the time that the dough needs to chill in order to be handled and rolled. You can do other things while the dough is chilling though!

I found that the best thing was to have two bowls for my stand mixer when I split my dough in half. You can also use a mixing bowl.

I prefer using a stand mixer because it's hands-free, but you could also use a handheld mixer. (We have and love it!)

Having two bowls, regardless of which mixer you use, makes it SO easy to make both sets of dough pretty much back to back without having to wash a dish in between.

Don't let the process intimidate you though. Luckily it's one of those types of recipes where even if you "mess it up" (which is hard to do), you're not going to end up with an inedible cookie, it just may not be picture perfect.

Save this Chocolate Peppermint Pinwheel Cookies Recipe for later

More Holiday Cookie Recipes

This post is brought to as part of The Sweetest Season, which is my friend Erin's annual cookie exchange!

Every year, she gets a group of food bloggers together to bring you a bevy of new cookie recipes to make for the holidays. This is the 10th year, which is amazing and exciting!

Cookies make the perfect gift. Why not make a few different varieties and make cookie box gifts? Or just make more snacks!

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This year we're raising awareness about and fundraising for Cookies for Kids' Cancer, a recognized 501(c)3 non-profit organization dedicated to funding research for new, innovative and less-toxic treatments for childhood cancer.

Since 2008, Cookies for Kids’ Cancer has granted nearly $17 million to pediatric cancer research in the form of 100+ research grants to leading pediatric cancer centers across the country. From these grants have stemmed 35+ treatments available to kids battling cancer today.

If you'd like to join us in this amazing cause, you can donate to our C4KC fundraising page.