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Holiday Cookie Recipe: Peppermint Sandwich Cookies

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Peppermint Sandwich Cookies

People have firm holiday cookie traditions. If you're my mom, for example, you can't have Christmas without Pfeffernüsse. Growing up, my sisters and I all scowled and made fun of the cookies, calling them "Heffernutters," all the while reaching for the jam thumbprints we loved. My college roommate couldn't have Christmas without her mom's Almond Horns, my best friend growing up loved her grandmother's recipe for Mexican Wedding Cookies, and in skyping with my boyfriend's mother last week I learned all about her infamous Nutmeg Logs. Everyone has one cookie that just does it for them.

For me, it never feels quite like Christmas without simple, frosted sugar cookies. Because it's often so busy leading up to the week of Christmas, I usually don't get around to them until the day before when my dad and two sisters gather for the annual "Cookie Day." When my parents divorced twelve years ago, it became important for both to claim what traditions they'd keep and to forge new ones. My mom got Christmas Eve with us, so my dad started "Cookie Day" so we could all do something together during the day. On Cookie Day, my sisters and I all choose one cookie recipe we want to try, give my dad a shopping list of ingredients, and gather after lunch on Christmas Eve Day with loads of take-home tins and enthusiasm. We spend the day baking, making hot chocolate and tea, and taking goofy photos.

mint frosting

Last year we made a new cookie that was part of my recipe testing for Marge at the time. I did housemade "oreo's" as part of my regular line-up but knew I wanted to tweak them for the holidays. They were a big hit (with the business and with my sisters) and so we're doing them again this year for Cookie Day. I believe this is the first reoccurring cookie to ever grace the Gordon Family cookie table. And it's worthy I assure you, and I'm excited to share the recipe with you today.


The nice thing about this recipe is that you can do it in stages and the cookies, even when put together, have quite an impressive shelf-life if kept in the fridge (I've kept them for a week and they've been just fine). The dough is a little finicky, and you must allow it to chill for the appropriate amount of time without letting it chill so long that it becomes hard as a rock and you really need to work relatively quickly when rolling them out. But they're no more difficult than any slice-and-bake log cookie when it comes right down to it, and they'll make your house smell like an early Christmas gift.

Making Oreos

Quickly, when you read the recipe, if you're anything like my own friends and family you're going to want to try and make these without Crisco. Don't. Trust me. I've tried. You need a little Crisco in the filling to help stabilize it. I know some people really hate using it and I get that, but the filling on these cookies will be a relative mess without it. Also, you'll get a feel for this dough the more you make these cookies. But in order to roll it, you need it to be quite firm but not rock hard. If you chill your dough for too long and it does become rock-hard simply put it in the microwave for 20 seconds and knead gently until it's more malleable. Happy holiday baking to all!

single oreo

Homemade Peppermint Sandwich Cookies
For the bittersweet chocolate in this recipe, I use a 60-72% Callebaut in the bakery and a Scharffen Berger semi-sweet chocolate. I splurge and use Valrhona cocoa powder as well. These are the kind of cookies where chocolate is a main ingredient and you really will be able to taste the difference between using a ho-hum chocolate and a really wonderful chocolate. And for the filling: some folks prefer a much sturdier filling than others, so add the confectioner's sugar slowly and know that you'll need to add more or less than the recipe calls for depending on your desired consistency.

Makes: 18-20 cookies

Prep Time (includes chilling and rolling the dough): 2 hours
Cook Time: 15 minutes
Total Time: 2 hours, 15 minutes

For Cookies:
1 cup (2 sticks) unsalted butter, melted and cooled slightly
1 cup sugar
1 1/2 teaspoons vanilla
1/2 cup semi-sweet chocolate, melted and cooled slightly
1/2 cup bittersweet (60-70%) chocolate, melted and cooled slightly
1 egg, room temperature
1 3/4 cup all-purpose flour
1/4 cup cocoa powder
1 tsp. kosher salt
1/4 tsp baking soda

For Filling:
5 ounces vegetable shortening
5 tablespoons unsalted butter, cubed and at room temperature
2 1/2 cups confectioners sugar, sifted
1/4 teaspoon salt
1/2 teaspoon peppermint extract
3-4 crushed candy canes, to top

1. In a medium bowl, whisk together the butter and sugar until well combined. Add the chocolate and vanilla and whisk together. Then add the egg and whisk until incorporated.

2. In a separate medium bowl, stir together the flour, cocoa powder, salt, and baking soda. Add the flour mixture into the chocolate mixture, stirring slowly with a wooden spoon or your hands (using my hands is easier for me at this point).

3. Let the dough firm up at room temperature for 30 minutes.

4. Dump dough out onto the counter or another flat surface and gather into one flat disk (just like you would with pie dough). Wrap in plastic wrap and refrigerate for 1 hour.

5. Preheat oven to 350 F. Lay one sheet of plastic wrap down on the counter and place to ball of dough on top. Knead it for a moment or two to soften it to the point where it will allow you to roll it out. Place another sheet of plastic wrap on top of the dough (it should be sandwiched at this point) and roll to about 1/8-inch thickness or 1/4 inch thickness for a thicker cookie. Don't stress too much about these measurements -- this will be a little trial and error and you'll learn to eye the thickness for the kind of cookie you want. If the dough becomes too sticky or difficult to work with, put back in the refrigerator for 10-15 minutes.

6. Line a cookie sheet with parchment paper and, using a 2-3-inch round cutter, cut out the cookie circles and place them on the sheet. They don’t spread much, so they can be pretty close together.

7. Bake for 10 minutes or until the edges are very slightly darkened—this is tough to tell given their already dark color, but you'll want your cookie to be set but still soft in the center. They firm up when cooled. Cool on the baking sheet for 2 minutes before transferring to a wire rack to cool completely before frosting.


8. To make the filling: using a hand blender, beat the butter, vegetable shortening, salt and peppermint extract until smooth. Then add the confectioners sugar slowly in 1/2 cup increments until creamy and until the filling reaches the consistency you like, about one minute. Using a piping bag (or just a good old fashioned spoon), pipe a generous portion of filling onto one completely cooled chocolate cookie, dust with crushed candy canes and cover with another chocolate cookie to make a sandwich.

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