Pumpkin Whoopie Pies with Chocolate Cream Cheese Filling

I am not the most enthusiastic of pumpkin dessert eaters, or makers. But many that join me at my Thanksgiving table each year are, indeed, just that: pumpkin lovers in kind of a big way. And because I do not want to disappoint, nor relinquish my sense of myself as the “hostess with the mostest,” I always make a pumpkin dessert (or even two) to be enjoyed post-turkey. Sometimes I make a pumpkin chiffon (or mousse) tart and sometimes I make a pumpkin sheet cake with chocolate bourbon butter cream and sometimes I make pumpkin whoopie pies with cinnamon cream cheese filling.  But this year, I think it is going to have to be pumpkin whoopie pies with chocolate cream cheese filling, and I’m hoping that maybe you want to join me in making them, as well. Pumpkin and chocolate is the most excellent of combos, and the tang of the cream cheese in the filling, plays off the dark chocolate flavor beautifully. The pumpkin “cookies” themselves, that sandwich the filling, are soft and flavorful and a delightful (and fun) departure from pie, just sayin’.

The recipe was originally published here, on Food52, but head to my website for a whole host of additional recipes perfect for Thanksgiving (and beyond . . . ).

Yield: 30 pies

For the whoopies:

  • 3 cups all-purpose flour
  • 1 1/4 tsp baking soda
  • 1 tsp baking powder
  • 1 tsp fine sea salt
  • 1 Tbsp cinnamon
  • 1 tsp nutmeg
  • 1/2 tsp cloves
  • 1/4 tsp white pepper
  • 1 cup extra-virgin olive oil, I like something fruity and bold
  • 1 1/2 cups light brown sugar
  • 1/2 cup granulated sugar
  • 1 Tbsp pure vanilla extract
  • 1 large egg
  • 1 yolk
  • 3 cups of pumpkin puree (from about one and half 15 ounce cans)

For the filling:

  • 1/2 cup unsalted butter, room temperature
  • One 8 oz. package cream cheese, room temperature
  • 1 Tbsp pure vanilla extract
  • 3 cups confectioners’ sugar
  • 3/4 cup Dutch process cocoa powder
  • 1/2 tsp fine sea salt

To make the whoopie pies, in a medium-sized bowl, whisk together the flour, leavenings, salt, and spices.

In a large bowl, combine the oil, sugars, and vanilla and whisk to combine. Add the egg and yolk, whisking after each, and then the pumpkin. Whisk a final time. Add the dry ingredients all at once and gently fold them into the wet, with a rubber spatula, mixing until the dry just disappears. Cover the bowl with plastic wrap and place in the fridge for about an hour.

Preheat the oven to 350-degrees and line two baking sheets with parchment paper. Using a 1 1/2 tablespoon cookie scoop or measuring spoons, scoop the batter on to the pans, leaving a few inches between each one.

Bake for about 10 to 12 minutes, rotating the pan at the halfway point. The pies are done when the tops are firm and dry to the touch, and lightly pressing with your finger does not leave an indent. Do not over bake. Repeat with the remaining batter.

Let the pies cool on the pans while you make the filling.

To make the filling, combine the butter and cream cheese in the bowl of a stand mixer fitted with the paddle attachment and on medium high speed, beat the butter/cream cheese until smooth and uniform. Add the vanilla and beat again.

Sift the confectioners’ sugar, cocoa powder and salt into a large bowl and whisk until combined. With the mixer on low speed, add about a cup of the sugar at a time to the mixer bowl, beating after each addition until thoroughly until combined. Once all of the sugar has been added, increase the speed of the mixer to medium or medium high, and beat the mixture until smooth. Do not over mix, or the frosting will lose structure.

Turn half of the whoopie pies over and using the same 1 1/2 Tbsp scoop, now cleaned, place a dollop of frosting on each one. Top with another pie. Serve immediately or refrigerate until you are ready to do so.

Whoopie pies can be eaten chilled from the refrigerator or you can let them come to room temp before serving. They will keep in the refrigerator, tightly wrapped in plastic wrap for up to 3 days.