Pumpkin Whoopie Pies with Cream Cheese Filling

The holidays are heading towards me at full speed so I'm making sure that I get a sufficient amount of baking and holiday movie watching into my schedule before it's time to kick the Christmas tree to the curb. I was going to make a sweet potato cheesecake for Thanksgiving, but was intimidated by the cheesecake water bath technique.

So I switched to chocolate covered clementines, but was scared off by the fact that clementines are only sold by the thousands it seems. I finally settled on Pumpkin Whoopie Pies which are like a cupcake in cookie form. I found this recipe easy, yet time consuming, but totally worth the 20 creamy pies it yields.

RECIPE (This is a Martha Stewart Recipe)

Makes 20 whoopie pies

For the Cream-Cheese Filling:

3 cups confectioners' sugar

1 stick unsalted butter, softened

8 ounces cream cheese, softened

1 teaspoon pure vanilla extract

For the Cookies:

3 cups all-purpose flour

1 teaspoon salt

1 teaspoon baking powder

1 teaspoon baking soda

2 tablespoons ground cinnamon

1 tablespoon ground ginger

1 tablespoon ground cloves

2 cups firmly packed dark-brown sugar

1 cup vegetable oil

3 cups pumpkin puree, chilled

2 large eggs

1 teaspoon pure vanilla extract

1. Preheat oven to 350 degrees. Line two baking sheets with parchment paper and set aside.

2. In a large bowl, whisk together the flour, salt, baking powder, baking soda, cinnamon, ginger, and cloves. Set aside. 

3. In another large bowl, whisk together the brown sugar and oil until well combined. Add the pumpkin puree and whisk until combined. Add in the eggs and vanilla and whisk until well combined. Sprinkle the flour mixture over pumpkin mixture and whisk it until fully incorporated.

4. Using a large tablespoon or ice cream scoop, drop heaping tablespoons of dough onto the baking sheets while rotating the utensil (rotating will create a round shape) creating 5" cookie rounds. Place them about 1 inch apart. Transfer cookies to oven (bake multiple batches if necessary) and bake until they're just starting to crack on top and a toothpick inserted into the center of each cookie comes out clean, about 15 minutes. Let them cool completely on the pan.

5. Meanwhile, make the filling by sifting the confectioner' sugar into a medium bowl. Set it aside. With an electric mixer, beat the softened butter until smooth. Add the cream cheese and beat until well combined. Add the confectioners' sugar and vanilla, and beat just until smooth. (This filling can be made up to a day in advance. Cover and refrigerate it, letting it stand at room temperature to soften before using.)

6. To assemble the whoopie pies, line a baking sheet with parchment paper and set it aside. Transfer the filling to a large zip-top bag and snip a corner of the bag. When the cookies have cooled completely, pipe a large blob of filling on the flat side of half of the cookies. Sandwich with remaining cookies, pressing down slightly so that the filling spreads to the edge of the cookies. 

7. Transfer the completed cookies to the baking sheet and cover them with plastic wrap. Refrigerate the cookies for at least 30 minutes before serving and for up to 3 days. Freeze any cookies that you will not eat within 3 days as they start to get too moist by the third day.