Chocolate-Peppermint Sandwich Cookies

So, here’s a little confession. I went so crazy making treats for the holidays last year that I ran out of time to share them all with you. January rolled around and I still had a handful of recipes I was excited about. I was really tempted just to post them anyway, but if I’ve learned one thing after blogging for nearly six years, it’s that no one wants to read about cookies and desserts for at least the first few weeks of the new year. So, I tucked these goodies into the archives for nearly an entire year, and now, finally, I can pull them out to see the light of day!

Here’s another secret: this isn’t the first year I’ve run into this problem, and it probably won’t be the last. I vote we make December another week longer. More time to enjoy the decorations, the lights, the music, and most importantly, the cookies! Um, and also – more days to blog about those cookies 🙂

These chocolate-peppermint sandwich cookies combine so many things I love. In fact, I struggle to think of any three words I’d rather see together during December than chocolate, peppermint, and cookies sandwiches! Peppermint is the best holiday flavor ever in my book and I’m kind of obsessed with cookie sandwiches. Usually, I lean toward the more cakey whoopie pies when it comes to cookie sandwiches (I even have a Pinterest board dedicated to them), but these were a great way to switch things up.

These cookies are chewy, almost brownie-like and are sandwiched around a peppermint-flavored buttercream. They lend themselves to lots of holiday variation too! I rolled the edges of mine in festive sprinkles, but you could use crushed candy cane pieces or just leave them plain if you wanted. You could also add a touch of red or green food coloring to the filling instead. Chocolate-peppermint sandwich cookies are already on my holiday baking list again this year, and I definitely think they should be on yours too 🙂

Chocolate-Peppermint Sandwich Cookies
barely adapted from Cook’s Country, December/January 2011

Cookies
1 1/2 cups all-purpose flour
3/4 teaspoon baking soda
1/2 teaspoon salt
1 cup semisweet chocolate chips
3/4 cup packed light brown sugar
5 tablespoons unsalted butter, at room temperature
1 tablespoon water
1 large egg, lightly beaten

Filling
1/2 cup (1 stick) unsalted butter, at room temperature
1/2 teaspoon peppermint extract
2 cups confectioners’ sugar
2-3 tablespoons milk (low-fat is fine)

sprinkles or crushed candy canes, to decorate

Preheat oven to 350 F. Line two baking sheets with parchment paper.

In a medium bowl, whisk together the flour, baking soda, and salt. Add the chocolate chips, brown sugar, butter, and water to a medium saucepan. Set over medium heat and cook, stirring frequently, until the chocolate and butter have melted, and the mixture is smooth. Transfer the mixture to a large bowl and whisk in the egg, then use a rubber spatula to mix in the dry ingredients just until barely combined.

Using a small cookie scoop (about 1 tablespoon), portion the dough onto the prepared baking sheets, leaving about 2 inches between the cookies. It’s important to try to make the cookies all roughly the same size so they’ll be easy to pair up for the sandwiches. Bake for about 8-9 minutes, or until the cookies are puffed and the edges are just barely set – the centers will be soft and look underdone, that’s ok. You really do not want to over-bake these cookies. Transfer the baking sheet to a wire rack and allow the cookies to cool for a few minutes before removing them to the rack to cool completely. Repeat with remaining dough.

To make the filling: Use a hand mixer to beat the butter, peppermint extract, confectioners’ sugar, and 2 tablespoons of the milk together in a medium bowl. If the consistency is too thick, add some (or all) of the remaining tablespoon of milk to achieve a thinner consistency.

Match the cookies in pairs by size. Transfer the filling to a piping bag and pipe a small amount onto the flat side of one cookie of each pair. Sandwich the cookies together, and press the filling to the edges. If desired, roll the edges of the cookies in festive sprinkles or crushed candy cane pieces. Store the cookies in an airtight container at room temperature for up to 2 days.

Makes about 18 sandwich cookies