Double Chocolate Peppermint Sandwich Cookies

Food

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Double Chocolate Peppermint Sandwich Cookies – Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They’re the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! Double Chocolate Peppermint Sandwich Cookie Recipe

One of my favorite things are chocolate sandwich cookies. Sinking my teeth into them and biting through the layers is just so satisfying.

And judging by the popularity of Oreos, I think the whole world loves chocolate sandwich cookies, too. But these cookies of mine absolutely blow any store bought cookie away!

My homemade, 100% from scratch, double chocolate peppermint sandwich cookies are comprised of rich and very chocolate cookies. They’re soft, chewy, and studded with both chocolate chips and peppermint chips.

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Between each sandwich cookie pair lays a sweet-and-tangy cream cheese filling. I just adore this because I am a huge cream cheese frosting person.

Finally, the cookies are rolled in crushed candy canes and drizzled with white chocolate over the top. 

I truly can’t think of a better holiday cookie! Between their impressive look, the bold chocolate flavor, and the notes of peppermint from both the peppermint chips and the crushed candy canes, everyone who is lucky enough to sample one of these chocolate peppermint sandwich cookies is going to fall in love with them.

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Ingredients in Chocolate Peppermint Sandwich Cookies and Filling

For these delectable chocolate cookies, you’ll need the following fridge and pantry ingredients to make the cookie dough:

  • Unsalted butter
  • Granulated sugar
  • Light brown sugar
  • Egg
  • Vanilla extract
  • Unsweetened cocoa powder 
  • All-purpose flour
  • Baking soda
  • Salt
  • Milk or semi-sweet chocolate chips
  • Andes Peppermint Crunch Baking Chips or similar

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

For the tangy-sweet cream cheese filling, you’ll need these ingredients to make the filling:

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

How To Make the Double Chocolate Peppermint Cookie Dough

This Christmas drop cookie dough is easy to make. Experienced bakers may note that the dough doesn’t need to be chilled. Now that’s what I call the season of giving!

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Let’s make Christmas cookies:

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Step 1: Preheat your oven to 350F

Step 2: Beat together the butter and sugars until fluffy.

Step 3: Add the egg, vanilla, and beat until creamy.

Step 4: Combine together the cocoa powder, flour, baking soda, and salt in a small bowl. Add it slowly to the mixing bowl and beat to combine.

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Step 5: Add the chocolate chips, peppermint chips, and stir.

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Step 6: Use a small cookie scoop to form dough balls.

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Step 7: Bake for 10 minutes and cool the cookies. While the double chocolate peppermint sandwich cookies cool, you can make the filling.

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Making the Filling for Peppermint Sandwich Cookies

To make the filling for your double chocolate sandwich cookies simply do the following:

Step 1: Beat the cream cheese and butter together.

Step 2: Add the confectioners’ sugar, then vanilla and salt, and beat until smooth.

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Assembling Double Chocolate Peppermint Sandwich Cookies

When you’re ready to assemble your double chocolate peppermint Christmas cookies, proceed by doing the following:

Step 1: Pipe or spoon icing onto the underside of a cookie all the way to the edges.

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Step 2: Place another cookie on top to form a sandwich and squeeze them together gently to seal.

Step 3: Roll the filling edge through crushed candy canes and allow them to set for 30 minutes.

Step 4: Melt the white chocolate and then drizzle it over the cookies, allow it to set, and then serve.

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

What Kind of Cocoa Powder Should I Use for Chocolate Sandwich Cookies?

Look for natural unsweetened cocoa powder. Something like Hershey’s that’s been around for ever is perfectly fine.

Or you can splurge on Scharffen Berger if you want to get fancy. It does have a more refined taste but use whatever suits you.

Do not use:

  • hot chocolate mix
  • previously sweetened cocoa powder
  • cocoa nibs
  • some fancy kind of “cacao” you find

I’ve never tested the recipe with Dutch process cocoa powder so can’t say if it will work or not.

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

What Kind of White Chocolate is Best For Melting?

Of all the types of chocolate, white chocolate is definitely the most finicky and tricky to melt. It is prone to seizing up and turning into a rock hard yet gritty mess that looks like a destroyed sand castle.

In order to avoid that, I highly recommend using white chocolate candy melts or wafers.

Specifically, the Ghirardelli White Chocolate Melting Wafers are great because they melt smoothly, evenly, and easily.

If you don’t want to spring for those, then my second choice recommendation is a high quality white chocolate candy bar like Lindt. The higher the fat content, the better and easier it will be to melt.

I do not recommend trying to melt white chocolate chips. They are little devils to be avoided for this purpose.

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

How To Store Peppermint and Chocolate Sandwich Cookies

Food storage purists would likely recommend storing these cookies airtight in the fridge where they will keep for about 2 weeks. 

However, generally speaking I don’t like storing baked goods in the fridge because it dries them out and changes the texture.

Therefore, I’m comfortable storing my double chocolate peppermint sandwich cookies airtight at room temp for up to about 3 days. After that, they belong in the fridge.

The confectioners’ sugar preserves the cream cheese and butter sufficiently for me, but do as you feel most comfortable.

You can also freeze these holiday sandwich cookies for 4 months in case you want to make them in advance.

If you know you’re going that route, then keep them unassembled. Just freeze off the baked cookies and then when you’re ready to serve them, make the filling, and then fill and assemble them as directed.

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Tips for the Best Double Chocolate Peppermint Sandwich Cookies

I’ve been as specific as possible in the recipe to help you make the best chocolate peppermint sandwich cookies. A few more specific tips and tricks include:

 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

  1. Peppermint chips are definitely a seasonal item. I like to use the Andes Peppermint Crunch Baking Chips. They are fairly easy to find year round on Amazon. If you’re waiting to see them in actual stores, after Thanksgiving but before Christmas is the window in stores like Walmart, Target, or well-stocked supermarkets. 
  2. To make life easier, I just buy crushed candy canes. Well worth the price paid to not have to smack candy canes inside a ziptop plastic bag with a rolling pin, but that method is also viable should you choose it.Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 
  3. Use a small cookie scoop to make the cookies all the same size. Otherwise it’s quite a chore trying to find a suitable match when creating the sandwiches. Leave the guesswork out and use a cookie scoop.
  4. If you still wind up with slightly unevenly sized cookies, while the cookies are still warm and on the baking sheet, use the back of a small spoon or butter knife and gently push in any awkward or edges that are “splooging” out to create more uniformly sized double chocolate peppermint sandwich cookies. This trick only works when the cookies are still quite warm.
  5. To fill the cookies, I like to use a ziptop bag and just snip an end off. However, you can use a piping bag.Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 
  6. After rolling the assembled sandwich cookies in the crushed candy canes, make sure to allow them to rest or set up or at least 30 minutes. This gives the candy cane bits a better chance of adhering. 
  7. Rather than just drizzling white chocolate over the assembled chocolate sandwich cookies, you can also dip half of the cookie in the white chocolate. You’ll need to melt more white chocolate than the recipe calls for, but this is definitely a decadent way to go for the holidays.Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! Double Chocolate Peppermint Sandwich Cookies - Rich, decadent, soft and chewy double chocolate cookies are sandwiched together with a tangy cream cheese filling. Rolled in crushed candy canes and drizzled with white chocolate for extra flavor and holiday festiveness! They're the PERFECT Christmas cookie! 

Ingredients

Cookies

  • 1/2 cup unsalted butter, softened
  • 1/2 cup granulated sugar
  • 1/2 cup light brown sugar, packed
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1/3 cup unsweetened natural cocoa powder
  • 1 cup plus 2 tablespoons all-purpose flour
  • 1 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1 cup semi-sweet or milk chocolate chips
  • 1/2 cup peppermint chips

Filling

  • 8 ounces cream cheese, softened (brick style, not in a tub or ‘spreadable’, not reduced fat nor lite)
  • 1/2 cup unsalted butter
  • 3 cups confectioners’ sugar, sifted if lumpy
  • 1 teaspoon vanilla extract
  • 1/4 teaspoon salt

Assembly

  • 1 cup peppermint candy canes, crushed
  • 1 cup white chocolate melting wafers

Instructions

  1. Cookies – Preheat oven to 350F and line two baking sheets with Silpat liners or spray well with cooking spray; set aside.
  2. To the bowl of a stand mixer fitted with the paddle attachment or large bowl and handheld electric mixer, add the butter, sugars, and beat until fluffy; about 3 to 5 minutes. Stop and scrape down the sides of the bowl.
  3. Add the egg, vanilla extract, and beat until fluffy, about 2 minutes. Stop and scrape down the sides of the bowl; set aside.
  4. To a separate medium bowl, add the flour, cocoa powder, baking soda, salt, and whisk to combine.
  5. Add the dry ingredients to the wet in the large mixing bowl, and beat until just combined; don’t overmix.
  6. Stir in the chocolate chips and peppermint chips* (See Notes) by hand.
  7. Using a small cookie scoop, make rounded teaspoon sized balls of dough.
  8. Place balls on prepared baking sheets spaced at least two inches apart, and if desired, add a few additional chocolate chips to the top of each dough ball.
  9. Bake for approximately 10 minutes, but start checking at 8 minutes because all ovens bake differently. Tip – For optimal results bake one sheet of cookies at time, on the center oven rack, and rotate baking sheet midway through baking to ensure even baking.
  10. Allow cookies to cool on baking sheet momentarily until they’re firm enough to be transferred to a wire rack; they will firm up as they cool. Tip – So don’t be afraid to pull them out of the oven if they don’t appear to be fully set.
  11. Filling – To the bowl of a stand mixer fitted with the paddle attachment or large bowl and handheld electric mixer, add the cream cheese, butter, and beat until fluffy; about 3 to 5 minutes. Stop and scrape down the sides of the bowl.
  12. Gradually add the confectioners’ sugar and beat to incorporate. Stop and scrape down the sides of the bowl.
  13. Add vanilla, salt, and beat to incorporate.
  14. Assembly – Pipe or spoon a ½-inch thick layer of filling on the underside of a cookie all the way to the edges.
  15. Place another cookie (the underside of it) on top, and lightly squeeze together to seal. Repeat until all cookies are gone.
  16. Roll the edges of the filling through crushed candy canes.** (See Notes) Allow to set for at least 30 minutes so they can adhered.
  17. To a small microwave-safe bowl, melt the white chocolate melting wafers as indicated on the packaging directions.*** (See Notes)
  18. Drizzle the melting white chocolate over the cookies using a small spoon. Alternatively you can place it inside a small baggie, snip the corner, and drizzle.
  19. See Notes**** below for storage options.

Notes

*Peppermint chips are definitely a seasonal item. I like to use the Andes Peppermint Crunch Baking Chips. They are fairly easy to find year round on Amazon. If you’re waiting to see them in actual stores, after Thanksgiving but before Christmas is the window in stores like Walmart, Target, or well-stocked supermarkets. 

**To make life easier, I buy crushed candy canes. Well worth the price paid to not have to smack candy canes inside a ziptop plastic bag with a rolling pin, but that method is also viable should you choose it.

***Of all the types of chocolate, white chocolate is definitely the most finicky and tricky to melt. It is prone to seizing up and turning into a rock hard yet gritty mess that looks like a destroyed sand castle. In order to avoid that, I highly recommend using white chocolate candy melts or wafers.

Specifically, the Ghirardelli White Chocolate Melting Wafers are great because they melt smoothly, evenly, and easily.

If you don’t want to spring for those, then my second choice recommendation is a high quality white chocolate candy bar like Lindt. The higher the fat content, the better and easier it will be to melt.

do not recommend trying to melt white chocolate chips. 

****Food storage purists would likely recommend storing these cookies airtight in the fridge where they will keep for about 2 weeks. 

However, generally speaking I don’t like storing baked goods in the fridge because it dries them out and changes the texture.

Therefore, I’m comfortable storing my double chocolate peppermint sandwich cookies airtight at room temp for up to about 3 days. After that, they belong in the fridge.

The confectioners’ sugar preserves the cream cheese and butter sufficiently for me, but do as you feel most comfortable.

You can also freeze these holiday sandwich cookies for 4 months in case you want to make them in advance.

If you know you’re going that route, then keep them unassembled. Just freeze off the baked cookies and then when you’re ready to serve them, make the filling, and then fill and assemble them as directed.

Nutrition Information:

Yield:

10

Serving Size:

1

Amount Per Serving:

Calories: 773Total Fat: 39gSaturated Fat: 23gTrans Fat: 0gUnsaturated Fat: 13gCholesterol: 98mgSodium: 380mgCarbohydrates: 103gFiber: 1gSugar: 86gProtein: 6g

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