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Chocolate Peppermint Sandwich Cookies

Whether you’ve snarfed down a package of peppermint creme Oreos, peppermint bark Oreos, candy cane Joe-Joes, or another store-brand box, you know that chocolate peppermint sandwich cookies are one of the greatest sweet snacks of the holiday season.

While I personally like to think of them as candy cane Oreos, it honestly doesn’t matter what you call them here.

Chocolate peppermint sandwich cookies are classic yet festive, and won’t give you as much of a hangover as eating a whole box of peppermint bark.

chocolate peppermint sandwich cookies in stacks
Photo: Casey Barber

With this post, I’m finally spilling my secrets on how to make the best homemade Oreos—with a holiday twist.

(The original recipe can be found in my first cookbook, Classic Snacks Made from Scratch, and if you’re looking for a Halloween variation, check out my candy corn Oreos recipe.)

An Oreo—ok, a chocolate sandwich cookie—has only two components: the cookie and the filling.

For the cookie, the texture needs to be firm, with a hint of crunchy crumble in each bite. It’s a cross between a sugar cookie and a sablé or shortbread.

chocolate peppermint sandwich cookies in stacks
Photo: Casey Barber

To achieve this, you need to roll your cookies to about 1/4 inch thick—too thin and they’ll shatter, too thick and they’ll get puffy and slightly soft.

The taste is just as crucial: these are bittersweet cookies, not milk chocolate cookies. The hint of bitterness comes from two key ingredients:

Secret Ingredient Number 1: Dark Cocoa Powder

Dark cocoa powder is not as difficult to find as it used to be when I was testing for the cookbook, but I think it’s worth seeking out the higher-end versions if you want a superior result.

You can likely find Hershey’s Special Dark cocoa powder in your local supermarket.

The formula was changed from an alkalized (Dutch-process) cocoa to a non-alkalized version, which means it’s not quite as rich in color or taste as it used to be. But it still works—I used it for the batch of cookies photographed here.

If you want super-dark cookies, you’ll have to seek out black cocoa powder for an intense, blackout-style color. Both Guittard and King Arthur Baking brands can be found online.

I’ll repeat—this is an intense color, so if I’m going this route, sometimes I’ll cut it with my Valrhona cocoa powder, which is dark but not midnight black.

Secret Ingredient Number 2: Baked Soda

If you were reading the recipe without my explanation, you might think I misspelled “baking soda.” But no—baked soda is a more concentrated, more alkalized version of baking soda.

(See what’s happening here? Bitter! Intense!)

As food scientist Harold McGee explained, heating baking soda converts it from sodium bicarbonate to sodium carbonate, making it a stronger alkali that can also be used to give soft pretzels their signature sheen and ramen noodles their color and bounce.

You know that slightly slimy feeling you get on your hands after swishing Oxi-Clean around to dissolve it in water? That’s alkaline!

Learn how to make baked soda in the recipe below.

chocolate peppermint sandwich cookies in stacks
Photo: Casey Barber

As for the sandwich cookie filling, it has its own set of qualifications.

I want it to be pliable and slightly icing-like, not a squishy-soft, marshmallowy frosting or a butter-based cake frosting.

So I keep it simple with a confectioner’s sugar base and just enough corn syrup and shortening that you can roll it up and squish it between those two chocolate cookies.

chocolate peppermint sandwich cookies in stacks
Photo: Casey Barber

Because these are chocolate peppermint sandwich cookies, the classic sugary filling needs to have a little bit of minty crunch.

So crushed peppermints or candy canes—whatever extras you have on hand—make the perfect addition. But that’s not all! Remember how I said that I like to think of these as candy cane Oreos?

I took another trick from my Halloween Oreos and dyed half the filling red. A little halfsie swirl inside the cookie just makes it that much more holiday-ready, in my opinion.

chocolate peppermint sandwich cookies in stacks

If food coloring is not your thing, no worries. Just leave it all white and use natural candy canes.

This chocolate peppermint sandwich cookie recipe might seem a little complex, but I promise you it’s worth it.

This has been one of my favorite homemade junk food recipes for years, and I hope the holiday version becomes a tradition in your home.

chocolate peppermint sandwich cookies in stacks

Chocolate Peppermint Sandwich Cookies

Yield: about 3 dozen filled cookies
Prep Time: 45 minutes
Cook Time: 15 minutes
Additional Time: 1 hour
Total Time: 2 hours

Chocolate peppermint sandwich cookies are the perfect homemade version of peppermint Oreos or candy cane Joe-Joes for the holidays.

Ingredients

Cookies

  • 3 cups (360 grams) all-purpose flour
  • 1/2 cup (40 grams) dark cocoa powder or black cocoa powder
  • 1 tablespoon baked soda (see Notes section below)
  • 1 1/2 teaspoons baking powder
  • 1 teaspoon kosher salt
  • 8 tablespoons (1 stick) unsalted butter, cut into 1/2-inch cubes
  • 1/2 cup (92 grams) vegetable shortening
  • 1 cup (200 grams) granulated sugar
  • 2 large eggs
  • 2 ounces (57 grams; a scant 1/2 cup) bittersweet or semisweet chocolate, coarsely chopped
  • 1/2 teaspoon vanilla extract

Filling

  • 2 1/2 cups (284 grams) confectioner's sugar
  • 2 tablespoons (42 grams) light corn syrup
  • 1 tablespoon vegetable shortening
  • 2 tablespoons milk, any fat percentage
  • 1/2 teaspoon peppermint extract
  • 2 tablespoons crushed peppermints or candy canes
  • red gel food coloring (optional)

Instructions

Make the cookies:

  1. Whisk the flour, cocoa powder, baked soda, baking powder, and salt together in a bowl, making sure to break up any cocoa powder lumps. Set aside.
  2. Add the butter, shortening, and sugar to the bowl of a stand mixer.
  3. Beat with the paddle attachment on medium speed for 2-3 minutes until lightened and fluffy, scraping down the sides of the bowl as necessary.
  4. Melt the chocolate in the microwave or in a double boiler, your preference. Set aside to cool slightly.
  5. Add 1 egg to the stand mixer and stir into the creamed butter on low speed just until combined. Scrape down the sides of the bowl and stir in the second egg.
  6. Add the melted chocolate and vanilla extract to the stand mixer and stir in on low speed until combined.
  7. Add the dry ingredients in 1/4-cup scoops, stirring until one scoop is mostly incorporated before adding the next. Scrape down the bowl one more time to make sure everything is well combined.
  8. Divide the dough into 2 pieces and wrap in plastic wrap.
  9. Refrigerate for at least 1 hour, until firm.
  10. Preheat the oven to 375 degrees F and line 2 large baking sheets with parchment paper or silicone liners.
  11. On a lightly floured rolling mat or clean work surface, roll out one of the chilled dough pieces until 1/4-inch thick.
  12. With a 1 1/2-inch round cookie cutter, cut out rounds of dough and place on the prepared baking sheets.
  13. Repeat with the second piece of dough.
  14. Bake the cookies for 10-12 minutes, until matte on top and slightly crispy at the edges.
  15. Cool completely on a wire rack before filling.

Make the filling:

  1. Add the confectioner's sugar, corn syrup, shortening, milk, and peppermint extract to the bowl of a stand mixer.
  2. Mix on medium-low speed with the paddle attachment until combined, scraping down the bowl as necessary.
  3. Stir in the crushed candy canes on low speed until combined.
  4. If making a red-and-white filling, divide the filling equally between 2 bowls (about 275-280 grams per bowl).
  5. Add a few drops of red gel food coloring to one bowl and stir until no streaks remain. It takes me about 4 drops to get the intensity of color I like, but you do you.

Assemble the sandwich cookies:

  1. Line half the cookies, flat-side up, on a clean work surface.
  2. Spoon a scant 1/2 teaspoon of the red filling and roll between your palms.
  3. Place on the cookie, and repeat with the white filling. (If you're only using white filling, use 1 scant teaspoon filling per cookie.)
  4. Top with the remaining cookies, smushing gently so the filling spreads to the edges of the cookie.

Notes

To make baked soda:

  1. Preheat the oven to 250 degrees F and line a rimmed baking sheet with a very large piece of foil, folding the foil’s edges up and over to create “sides” that prevent the baking soda from sliding onto the baking sheet itself.
  2. Pour baking soda onto the foil and spread in an even layer.
  3. Bake for about an hour, until the baking soda has dried slightly and reduced in weight; it’ll look more powdery.
  4. Allow to cool completely on the baking sheet. Store in a Mason jar or other nonreactive container with a tight-fitting lid for up to a year.

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Nutrition Information:
Yield: 36 Serving Size: 1
Amount Per Serving: Calories: 92Total Fat: 4gSaturated Fat: 2gTrans Fat: 0gUnsaturated Fat: 2gCholesterol: 17mgSodium: 82mgCarbohydrates: 12gFiber: 0gSugar: 4gProtein: 2g

The nutritional information above is computer-generated and only an estimate.

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