I won't lie: these are some fussy little cookies. They involve a great deal of rolling and filling and pressing and coating. And also waiting until you can finally (finally!) take your first buttery, peppermint-filled bite. But oh my, what a bite that is. Which is why my brother and I begged for them every Christmas, and why my mother required very little persuasion before pulling out the baking sheets.
These are supremely tender cookies, snapping like shortbread when you bite into them and then melting on your tongue. The combination of the peppermint coating and the peppermint cream filling give the cookies a sweet mintiness that can only be described as just right. I have never seen or tasted anything quite like them.
My mother thinks it likely that my grandmother originally found this recipe in an old Lutheran church cookbook. All she knows for sure is that she grew up begging for them every Christmas as well.
My grandmother made these cookies as balls, shaping nubs of dough around her thumb before stuffing each cookie with peppermint cream. My mother decided it was easier and more festive to sandwich the filling between two cut-out cookies and press the edges closed. I agree and have continued making them this way. Rounded shapes like hearts and bells work better than skinny or delicate shapes like stars and candy canes.
Peppermint pillow candies or peppermint straws are an absolute must for this recipe. These candies are lighter and more porous than the normal hard peppermints and can be ground easily. Unfortunately, these candies are getting harder and harder to find these days and are most easily picked up online. If you can only find the hard kind, smash them with a hammer inside a plastic bag rather than risk damaging your food processor blade.
Another persnickety aspect to this recipe is the dough. When first mixed, it's too soft to roll out. But after some time in the fridge, it's too hard. Let it rest on the counter for a good half hour before rolling it out. Even so, the dough may crack as you roll it. That's fine (though admittedly aggravating). Just smoosh the cracks closed and carry on. You can also re-roll the scraps several times without fear of toughing the cookies.
Persistence is rewarded. These cookies speak for themselves.
For the Dough: 1 cup (8 oz) butter, softened 1/2 cup (2 1/2 oz) powdered sugar 2 1/2 cups (12 1/2 oz) all-purpose flour
For the Peppermint Coating: 30 peppermint pillow candies (enough to make 1/2 cup crushed) 1/2 cup (2 1/2 oz) powdered sugar
For the Filling: 1 tablespoon cream cheese 1/2 tablespoon milk 1/2 cup (2 1/2 oz) powdered sugar 3 tablespoons peppermint coating mixture red food coloring milk for sealing the cookies
To make the dough: Beat together the butter and powdered sugar at high speed until creamy and light lemon colored. Scrape down the sides of the bowl, add the flour, and be1t at low speed until the dough comes together and no more dry flour is visible.
Turn the dough out on the counter and gather it into a ball. Separate the dough in two and flatten each into a 1-inch thick disk. Refrigerate for at least two hours or up to a day.
To prepare the coating: Place the peppermint candies in the bowl of a food processor. Process continuously until the candies are ground into a powder. Be forewarned: this will make an unholy racket that will scare the cats and wake the neighbors. Alternatively, place all the candies in a plastic bag, go outside, and smash the candies with a hammer. Mix the powdered candies with the powdered sugar and set aside.
To prepare the filling: Whisk together the cream cheese and milk. Whisk in the powdered sugar, three tablespoons of the powdered peppermint coating, and 1-3 drops of food coloring (one drop makes a pink filling, three will make a red filling). Whisk to form a smooth frosting-like paste.
To assemble the cookies: Sprinkle the counter with a little powdered sugar and set one of the rounds of dough on top. Let the dough warm for about a half an hour until it has softened enough to roll out.
Preheat the oven to 350°F.
Sprinkle the top of the dough and the rolling pin with more powdered sugar. Roll the dough from the middle outwards to make a circle roughly 1/8" thick. If the dough cracks as you roll it, just smoosh it back together with your fingers and carry on. Cut out shapes with cookie cutters, making sure you end up with an even number of each shape. Cookie shapes with large spaces in the middle work best for these cookies. (Think hearts and bells as opposed to stars or candy canes.)
Transfer half of the cookies to a parchment-lined baking sheet and space them an inch apart. Place a dab of filling in the middle of each cookie, no more than 1/4 teaspoon. Try not to get ambitious here or the filling will ooze out in the oven. Brush the edges of the cookies with a little milk and then sandwich the filling with another cookie. Seal the edges with the tines of a fork.
Gather up the dough scraps and re-roll it to cut out a few more cookies. Continue until the scraps are too small or the dough too soft. Refrigerate the remaining to combine with the scraps from the second disk of dough.
Bake the cookies for 12-15 minutes until the edges of the cookies just start to turn golden-brown. While the cookies are still hot from the oven, drop them one at a time into the peppermint coating. Turn the cookie over to make sure it's are coated evenly, then transfer it to a wire rack to cool completely. Repeat with coating the remaining baked cookies, then repeat the whole process with the second disk of refrigerated dough.
Store cookies in an airtight container on the counter. They will keep for several days. Leftover filling can be mixed with more powdered sugar to make a frosting for other sugar cookies.