American

Pumpkin Whoopie Pies With Chocolate Cream Cheese Filling

October 17, 2019
Photo by Bobbi Lin. Food stylist: Anna Billingskog. Prop stylist: Brooke Deonarine.
Author Notes

Pumpkin whoopie pies are just about the best way I know to celebrate the seasonal flavors of the fall. Whether you donate them to the Harvest Festival bake sale at the kids’ school, or enjoy them as an indulgence post leaf-peeping over a long weekend weekend, or as an alternative to (not) everyone’s favorite pie on Thanksgiving, or even as a cake substitute for birthdays (mine's on November 30th, if you’re curious)—nothing says “perfect, autumn sweet” like pumpkin whoopie pies. And if they’re filled with a tangy, dark and deeply chocolatey (thanks to Dutch process cocoa powder) cream cheese frosting, then all the better.

Not everyone realizes that pumpkin and chocolate is a winning combo—but I’m here to tell you it is. I like to use a bold-flavored olive oil in these to keep them moist and give them some more depth of flavor, but the resulting flavor is not super intense—you can barely taste the olive oil! And if you make the little cakes the day prior to assembling them, do not encase them in plastic wrap: merely keep them, face down, on your cookie sheet on the counter. They get a tad too soft when wrapped up. —Jessie Sheehan

  • Prep time 1 hour 15 minutes
  • Cook time 10 minutes
  • Makes 30 whoopie pies
Ingredients
  • For the whoopie pies
  • 3 cups all-purpose flour
  • 1 1/4 teaspoons baking soda
  • 1 teaspoon baking powder
  • 1 teaspoon fine sea salt
  • 1 tablespoon ground cinnamon
  • 1 teaspoon ground nutmeg
  • 1/2 teaspoon ground cloves
  • 1/4 teaspoon 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 tablespoon pure vanilla extract
  • 1 large egg
  • 1 egg yolk
  • 3 cups of pumpkin puree (from about one and half 15 ounce cans)
  • For the filling
  • 1/2 cup unsalted butter, room temperature
  • 1 8 oz. package cream cheese, room temperature
  • 1 tablespoon pure vanilla extract
  • 3 cups confectioners' sugar
  • 3/4 cup Dutch process cocoa powder
  • 1/2 teaspoon fine sea salt
In This Recipe
Directions
  1. For the whoopie pies
  2. To make the whoopie pies, in a medium-sized bowl, whisk together the flour, leavenings, salt, and spices.
  3. 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.
  4. Preheat the oven to 350°F 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.
  5. 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.
  6. Let the pies cool on the pans while you make the filling.
  1. For the filling
  2. 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.
  3. 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.
  4. 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.
  5. 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.

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Jessie Sheehan is a cookbook author, food writer, recipe developer, and baker. She is the author of The Vintage Baker and the co-author of Icebox Cakes (both published by Chronicle Books). She has developed recipes for many cookbooks, besides her own, and has contributed recipes/and or written for Better Homes & Gardens, Rachael Ray Everyday, The Washington Post, Epicurious, Food52, Fine Cooking, TASTE, Chowhound, The Spruce Eats, Little Sous, and Main Street Magazine, among others. She blogs at jessie sheehan bakes and can be found on Instagram at @jessiesheehanbakes. She likes layer cakes with lots of frosting and cookies that are thick and chewy. Oh, and she has a soft spot for chocolate pudding. She lives in Red Hook, Brooklyn, with her husband and two boys, not far from her beloved Baked, the bakery where she got her start.