For the cookie cakes
½ cup firmly packed light brown sugar
½ cup granulated sugar
8 tablespoons (1 stick) unsalted butter, at room temperature
¼ cup molasses
1 large egg
1 cup pumpkin puree, fresh or canned
2 cups all-purpose flour
1 teaspoon baking soda
1 ½ teaspoons ground cinnamon
½ teaspoon freshly grated nutmeg
¾ teaspoon kosher salt
½ cup whole milk
Confectioners’ sugar, for dusting
For the cream cheese filling
6 tablespoons unsalted butter, softened
6 tablespoons cream cheese, softened
¾ cup confectioners’ sugar
¾ teaspoons freshly grated orange zest (about ½ orange)
½ teaspoon pure vanilla extract
1. Position a rack in the center of your oven. Preheat the oven to 350˚F. Line a cookie sheet with parchment paper.
2. To make the cookie cakes: In the bowl of an electric mixer fitted with the paddle attachment, mix together the brown and white sugars on low speed to get rid of any lumps. Add the butter, and beat together until light and fluffy, 1 to 1 ½ minutes. Add the molasses and egg, and mix to combine. Scrape down the sides of the bowl. Add the pumpkin puree and mix to combine.
3. In a separate bowl, whisk together the flour, baking soda, cinnamon, nutmeg and salt.
4. Add the flour mixture to the pumpkin mixture in three batches, alternating with the milk. Mix well after each addition. Scrape down the sides of the bowl. Blend thoroughly, but do not overbeat.
5. Drop the dough by rounded teaspoonfuls onto the prepared cookie sheet. Bake for 12 to 15 minutes, or until a toothpick inserted into the center of one of the cookies comes out clean. Remove to a wire rack to cool completely before filling. Do not underbake.
6. To make the filling: In the bowl of an electric mixer fitted with the paddle attachment, combine the butter, cream cheese, confectioners’ sugar, zest and vanilla. Start mixing on low speed and then continue on medium speed until just fluffy and smooth, 2 to 3 minutes. Do not overbeat.
7. To complete the cookie cakes: Turn half of the cookies upside down onto a freshly lined cookie sheet.
8. Using a pastry bag fitted with a ¼-inch round pastry tip (Ateco #801 or use a resealable plastic bag with a corner cut off or a teaspoon), pipe or place about 1 teaspoon of filling onto each upside-down cookie cake. Place the remaining cookie cake halves (right side up!) on top. I skipped the pastry bag and just spread with a small spatula. Be careful though as the cookies have the texture of cake and might fall apart if not handled gently.
9. Refrigerate briefly until set, 15 to 20 minutes. Dust with confectioners’ sugar before serving.
Keep the cookie cakes refrigerated in an airtight container for up to 4 days.