Pumpkin Whoopie Pies with Cream Cheese Filling

My son, Parker, used to eat everything I tried to feed him up until he was about 15 months old. Now he is nearing 19 months and gives me the tight-lipped, “I refuse to eat that concoction you call food” face. That is until I fed him these. I did not even assemble them yet, I just grabbed one that was still slightly warm off the cooling rack and gave it to him as a pre-dinner snack. The first look he gave me was one that made me think he was going to throw it to the floor for the dog, but for some reason he gave it a second look and took a bite. He then proceeded to eat two more whoopie pie halves, followed by a pretty complete dinner, summed up with half of a completed pumpkin whoopie pie. Now for those of you out there who think that I am a terrible mother for feeding my son cakes instead of healthy vegetables, I hear you. I was feeling pretty guilty about it myself, but then I rationalized that there is healthy pumpkin in these and dairy and protein in the cream cheese filling. I am not saying that I am going to feed him like this all the time, but it was truly great to see him eat without fighting with me.

Ingredients:

• 3 cups (383 g, ) all-purpose flour
• 1 TB + 1 tsp. ground cinnamon
• 1 tsp. baking powder
• 1 tsp. baking soda
• 1 tsp. salt
• 1 tsp. ground ginger
• 1/4 tsp. ground cloves
• 1 tsp. pumpkin pie spice
• 3/4 cup sugar (152 g,
• 3/4 cup dark brown sugar (152 g,
• 3/4 cup canola oil (143 g, )
• 2 cups pumpkin puree (canned or fresh)
• 2 large eggs
• 1 tsp. pure vanilla extract

For the filling:

• 2 1/2 cups powdered sugar, sifted
• 8 ounces cream cheese, at room temperature
• 4 ounces (1 stick) unsalted butter, at room temperature
• 1 tsp. pure vanilla extract

Procedure

1. Preheat your oven to 350 degrees F, with the oven racks spaced evenly apart for even air circulation. Line 2 baking sheets with parchment paper or a silpat.
2. In a medium bowl whisk together the flour, cinnamon, baking powder, baking soda, salt, ginger, cloves, and pumpkin pie spice.
3. In a large bowl or the bowl of a stand mixer combine the sugars and the oil together. Mix together with a spoon or the paddle attachment until no lumps of dark brown sugar are visible. (Dark brown sugar doesn’t dissolve as well as white so sometimes it needs extra mixing to fully incorporate.) Add the pumpkin puree and stir to combine. Add in the eggs and vanilla and mix until fully combined, about 30 seconds.
4. Add the flour mixture to the pumpkin and sugar mixture and stir until fully combined. Allow the batter to rest for 5-10 minutes so it will thicken up. This will make it easier to scoop and it will also keep the cakes from spreading too much during baking.
5. Use a small cookie scoop (I used one that was probably a little over a tablespoon) or a large tablespoon to drop a rounded blob of dough onto the prepared baking sheets, at least 1 inch apart.
6. Bake for 9-12 minutes (my oven was exactly 10), rotating the pans from top to bottom once during baking). A toothpick inserted in the center will come out clean. I prefer slightly under baking versus over baking, that way they are not too dry.  Remove the cakes to a wire cooling rack and allow to cool completely before filling them. Repeat with two more trays of dough.
7. To make the filling: beat the butter until it is very smooth, add the cream cheese and beat again until very smooth and fully combined, about 2 minutes. Add the powdered sugar and beat until no dry sugar remains. Add in the vanilla and beat until smooth.
8. Assembling the whoopie pies:   I first tried to find matches for all my pies, because even though you try to make them as even as possible, inevitably some pair up better than others. On the flat side of half the cakes spoon out 1 tablespoon of filling. Then take its match and place it flat side down on top of the filling. Press down slightly so that the filling spreads to the edges of the cake. Repeat on the rest of the cakes. Allow the cakes/cookies to set up in the refrigerator for 30 minutes. For some reason the flavors really come through better when they have the chance to cool down. Makes approximately 24 assembled whoopie pies.