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Prep time
1 hour 15 minutes
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Cook time
10 minutes
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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
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Ingredients
- For the whoopie pies
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3 cups
all-purpose flour
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1 1/4 teaspoons
baking soda
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1 teaspoon
baking powder
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1 teaspoon
fine sea salt
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1 tablespoon
ground cinnamon
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1 teaspoon
ground nutmeg
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1/2 teaspoon
ground cloves
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1/4 teaspoon
white pepper
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1 cup
extra-virgin olive oil, I like something fruity and bold
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1 1/2 cups
light brown sugar
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1/2 cup
granulated sugar
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1 tablespoon
pure vanilla extract
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1
large egg
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1
egg yolk
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3 cups
of pumpkin puree (from about one and half 15 ounce cans)
- For the filling
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1/2 cup
unsalted butter, room temperature
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1
8 oz. package cream cheese, room temperature
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1 tablespoon
pure vanilla extract
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3 cups
confectioners' sugar
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3/4 cup
Dutch process cocoa powder
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1/2 teaspoon
fine sea salt
Directions
- For the whoopie pies
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To make the whoopie pies, in a medium-sized bowl, whisk together the flour, leavenings, salt, and spices.
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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.
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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.
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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.
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Let the pies cool on the pans while you make the filling.
- For the filling
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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.
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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.
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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.
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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.
Jessie Sheehan is a celebrated cookbook author, recipe developer, baker, and host of Cherry Bombe’s baking podcast, She’s My Cherry Pie. She is the self-proclaimed queen of “easy-peasy baking;” and has contributed recipes and writing to The New York Times, The Washington Post, Epicurious, Food52, Bon Appetit, and more. Her third cookbook, Snackable Bakes: 100 Easy-Peasy Recipes for Exceptionally Scrumptious Sweets and Treats was a New York Times best cookbook of 2022. And its savory sibling Salty, Cheesy, Herby Crispy Snackable Bakes, was published in the fall of 2024.
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