Pumpkin Whoopie Pies with Vanilla–Cream Cheese Filling

Vanilla–Cream Cheese Filling:

• 4 ounces cream cheese, softened
• 5 tablespoons unsalted butter, softened
• 1 teaspoon vanilla extract
• 1/8 teaspoon table salt
• 3 cups confectioners’ sugar, divided  

Pumpkin Whoopie Pies:

• 1 1/2 cups all-purpose flour
• 1 teaspoon ground ginger
• 1/2 teaspoon ground cinnamon
• 1/2 teaspoon baking powder
• 1/2 teaspoon baking soda
• 1/2 teaspoon table salt
• 1 cup pumpkin purée
• 1 cup packed light brown sugar
• 1/2 cup canola oil
• 1 large egg
• 1 tablespoon dark molasses

Make the vanilla–cream cheese filling: in the bowl of an electric mixer fitted with the paddle attachment, beat together the cream cheese and butter on medium speed until the mixture is light and fluffy, about 3 minutes. Scrape down the sides of the bowl with a rubber spatula.

With the mixer running on low speed, gradually add the vanilla, salt, and about 2 1/2 cups of the confectioners’ sugar; beat for 1 minute. Scrape down the sides of the bowl. If the consistency is too soft to hold its shape, add more confectioners’ sugar a tablespoon at a time until you reach the desired consistency. If the filling is too stiff, add a few drops of milk.

Store in the refrigerator in an airtight container with plastic wrap pressed onto the surface of the filling for up to 5 days.

Make the whoopie pies: preheat the oven to 350°F and line a baking sheet with parchment paper.

In a medium bowl, whisk together the flour, ginger, cinnamon, baking powder, baking soda, and salt.

In the bowl of an electric mixer fitted with the paddle attachment, beat the pumpkin purée, brown sugar, oil, egg, and molasses for 3 minutes at medium speed. Thoroughly scrape down the sides of the bowl with a rubber spatula. With the mixer running on low speed, gradually add the flour mixture for a total mixing time of 30 seconds. Carefully scrape down the sides of the bowl with a rubber spatula.

Using a pastry bag fitted with a large plain tip (the hole should be about as large as the tip of your ring finger), pipe 2-inch-wide circles onto the prepared baking sheet, leaving 1 1/2 inches between them. Keeping your pastry bag completely vertical will help to achieve nice circles. (If you’re baking the pies in batches, refrigerate the batter before piping and baking a new batch.)

Bake for 10 minutes. Rotate the baking sheet and bake 8 to 10 more minutes until the whoopie pies have a deep orange color and spring back when touched. Remove from the oven and let cool completely.

To fill the whoopies, turn half of them over so that they are bottom-side up. Using a pastry bag, pipe a small dollop of vanilla–cream cheese filling onto each whoopie bottom. Top with the remaining whoopies.