American

Pumpkin Whoopie Pies With Chocolate Cream Cheese Filling

by:
October 17, 2019
4.6
5 Ratings
Pumpkin Whoopie Pies With Chocolate Cream Cheese Filling
Photo by Bobbi Lin. Food stylist: Anna Billingskog. Prop stylist: Brooke Deonarine.
  • Prep time 1 hour 15 minutes
  • Cook time 10 minutes
  • Makes 30 whoopie pies
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

What You'll Need
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
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.
Tags:

See what other Food52ers are saying.

  • Susan Block
    Susan Block
  • Jessie Sheehan
    Jessie Sheehan
  • judy
    judy
  • Yeamon420
    Yeamon420
Jessie Sheehan
Bio: Jessie Sheehan is the author of The Vintage Baker and Icebox Cakes. Her new easy-peasy baking book, Snackable Bakes, hits shelves in spring 2022. She contributes to the Washington Post, Bon Appétit, Food Network, and the Kitchn, among others.

Popular on Food52

7 Reviews

Susan B.
Susan B. October 22, 2019
I was thinking of your journey while I made this recipe. Followed the directions and they came out beautifully. They taste delicious and I am expecting them to be a big hit.
 
Jessie S.
Jessie S. October 23, 2019
Susan!! Yay! Love that u made these and that they came out beautifully (and that u thought of my journey while u did so). So sweet and nice to hear. Hope you and yours find them yummy. XO
 
judy
judy October 19, 2019
I would omit the oil in the cookie recipe and replace with the butter that is called for in the filling. And leave it out of the filling altogether. Neither addition sounds appetizing to me at all. The concept it good though.
 
Jessie S.
Jessie S. October 19, 2019
Sounds like you’ve got a plan for making them just the way you like them! Let me know how they turn out.
 
Yeamon420
Yeamon420 October 21, 2019
Hi Jessie I'm just finishing up my 35 rounds of radiation for throat cancer and and 12 rounds of chemotherapy. I'm always hungry and I'm looking for some food I can swallow food nutrition. After reading your article I know you get it as far as food goes. Im always hungry and your recipe sounds like the bombs. At 62 yrs old I'm weak from the treatment because I lost 81lbs in months. Please let this Rastamon who lost all of dreadlocks if you have any recipes or suggestions.
 
Jessie S.
Jessie S. October 21, 2019
I am so happy to hear that you are finishing up your treatment. Unfortunately, I am not able to make suggestions about nutritious recipes that make sense for you post-treatment. I found it very helpful to speak to the nutritionist at the hospital where I received my chemo treatments, about food choices during and after treatment and perhaps you could try that, as well. Best of luck.
 
Jessie S.
Jessie S. September 8, 2020
I am so happy to hear that you are finishing up your treatment. Unfortunately, I am not able to make suggestions about nutritious recipes that make sense for you post-treatment. I found it very helpful to speak to the nutritionist at the hospital where I received my chemo treatments, about food choices during and after treatment and perhaps you could try that, as well. Best of luck.