I think I just ate the last of these. And boy, do I miss them already.
Some cookies are destined to the holiday ghetto: unique and lovely, yet irretrivably intertwined with Christmas. Cookies like Mexican wedding cakes, or rum balls, or nut cups only make an appearance in December.
These chocolate sandwich cookies with peppermint filling are different. Grandma D. made them every year for Christmas, but their warm chocolate and fresh mint flavors work anytime. They’re made from an easy-to-work-with rich chocolate dough, rolled out and cut out and baked, and then paired to sandwich a peppermint-flavored buttercream frosting filling.
How do I love thee, choco yum yum?
I like them because they’re versatile. The recipe normally calls for using a 2-inch round cutter, which is the size pictured. This makes a good-sized sandwich cookie somewhat bigger than an Oreo. In the past I’ve done 1-inch rounds — bite size! yummy! — as well as 3-inch huge rounds and cutout shapes like animals or holiday theme shapes.
I like them because they make a lot. I don’t know the origin of this recipe, but I get the feeling Grandma doubled it when she typed it up. Yes, she typed up recipes. On a typewriter; this was ancient times, remember.
Sheesh. And you people call me anal. Where do you think I get it? It’s not my fault!
I like them because squirting frosting onto cookie halves is a kind of fun everyone should get to experience.
I like them because Chocolate. Sandwich Cookies. With Peppermint Filling. That’s why.
Chocolate Sandwich Cookies with Peppermint Filling Recipe
I haven’t put it through its paces yet, but the chocolate dough for these cookies feels very versatile. I bet it could easily be rolled super-thin for crisp chocolate wafers. The dough should be refrigerated before rolling, but let it rest outside the fridge for 10–20 minutes to let it warm up enough to roll out. I’ve made a lot of adaptions to the original — we don’t use oleo (margarine) anymore, and I made my own frosting, for starters. I did use shortening as the recipe calls for, but feel free to sub all butter.
special equipment: A stand mixer is very handy.
yield: An awful lot. Several dozen. Cut the recipe in half if you’re scared. But try the whole thing if you have room to freeze some!
Chocolate Sandwich Cookies:
4 cups all-purpose flour, preferably unbleached
1 teaspoon baking powder
1 teaspoon salt
6 squares unsweetened chocolate (6 ounces)
2 cups sugar
½ cup vegetable shortening or unsalted butter
½ cup unsalted butter, softened
½ cup milk
2 teaspoons vanilla extract
In a large bowl, sift together flour, baking powder, and salt. Set aside.
Melt chocolate in the microwave in a glass (or otherwise microwave-safe) container. It should take 20 to 45 seconds or so depending on your microwave’s power. Stir to get remaining clumps to melt. If they don’t, microwave a few seconds longer.
Cream sugar, shortening, and butter, preferably using a stand mixer. Mix in the eggs. Add melted chocolate, milk, and vanilla extract and mix. Add half the dry ingredients (the flour, baking powder, and salt you sifted together earlier), mix until incorporated, and add the rest of the dry ingredients until well combined.
You should have a smooth, dense, somewhat dry, dark brown dough. Separate dough into four pieces, wrap in plastic wrap, and refrigerate for at least an hour. After removing the dough from the fridge, let it warm for 10 to 20 minutes before trying to roll it. Super cold dough will be a pain to roll!
On a floured surface, roll the dough out to 1/8-inch thick. Cut with a 2-inch round cookie cutter, or any cookie cutter you desire. Gather and re-roll scraps.
Place cookies on ungreased cookie sheets. Bake at 400°F for 6 to 8 minutes, or to desired crispness. Remove from cookie sheets and cool on wire racks.
At this point, the chocolate cookie wafers can be stored and/or frozen until you’re ready to make sandwiches of them, or you can make them into chocolate sandwich cookies right away!
Peppermint Filling for Chocolate Sandwich Cookies
This is a basic buttercream frosting.
⅓ cup butter, softened
4 cups powdered sugar
¼ cup milk
1 teaspoon vanilla extract
½ teaspoon peppermint extract
drop or two of green or pink food coloring
In a large bowl, beat the butter all by its lonesome until it’s kind of fluffy. Add 2 cups of the powdered sugar, and mix until well-combined. This always takes longer than I always think, so be patient — it really will all mix together eventually.
Add the milk, vanilla, and peppermint extract and mix well. Beat in the rest of the powdered sugar, bit by bit. Add 1-2 drops of green or pink food coloring and blend. If the filling seems too thick, thin by adding more milk a teaspoon at a time.
Spread frosting on chocolate sandwich cookie halves, either with a knife or with a pastry bag. I borrow Sis’ decorating set and use the flower tip because it’s wide and because we only have like 3 tips. It makes filling go much faster than if you use the slow old knife.
Top filled halves with another cookie and there you have ‘em: chocolate sandwich cookies with yummy peppermint filling.