Whoopie!!! That’s what I want to say when I bite into one of these.

Rich buttercream filling that’s sandwiched between two very soft and tender pumpkin cookies. It doesn’t get much better.

Pumpkin Whoopie Pies

I loved how melt-in-my-mouth soft and moist these cookies were, which I attribute to three major ingredient choices. First, brown sugar is used exclusively, which renders cookies softer and moister than using granulated sugar.

Secondly, oil rather than butter is used, which keeps muffins and cakes extra moist. And finally, the pumpkin puree tenderizes and moistens the batter. Anything made with any or all of those ingredients usually turns out especially soft, moist, and tender and the cookies are no exception.

Pumpkin Whoopie Pies on white plate

The batter for the cookies is like pumpkin cupcake batter. As I was pouring it onto baking sheets, I was thinking, am I really doing this? It was so soupy, and I was worried, but it turns out I had no reason to be.

I hate dealing with piping bags but if you think that would be easier, be my guest. I just don’t like that so much of the precious cargo gets stuck to the sides and is wasted.

I used a one-quarter cup measuring cup and scooped batter from the mixing bowl onto baking trays, not quite filling the cup full. Because there’s a decent amount of oil in the batter, it slid right out of the measuring cup. Like butter. And I placed six mounds of dough on each of the two baking trays.

Pumpkin tops and bottoms on baking sheet

I only yielded 6 completed whoopie pies. My whoopie pies were borderline extra-large but because the pumpkin cookies are soft and light, extra-large didn’t seem ridiculously huge.

Two huge cookies with nearly one inch-thick buttercream filling didn’t seem ridiculously huge to me. Okay moving on.

Pumpkin whoopie pie

My first batch of whoopie pies disappeared far too quickly. I loved them so much, I made a second batch, and I increased the amount of spices. I nearly doubled the amounts of cinnamon, ginger, cloves and tossed in some pumpkin pie spice because I love robust, intense, and bold flavors when it comes to warming spices. Extra cinnamon, yes please. Plus, pumpkin stands up incredibly well to boldly spiced treats. A dash of molasses or maple would also be nice.

I just wanted to pick off these little morsels and squish them between my fingers. The cookies are soft and remind me of my days squishing Little Debbie Oatmeal Cream Pies as a kid.

Pieces of pumpkin whoopie pie

Some people make the filling with vegetable shortening, but I prefer butter in my buttercream, because the flavor can’t be beat. However, the advantage to using shortening is that is has much more structure than butter and so the filling is firmer, holds up better, and has more density and less squish than a butter-based buttercream.

Buttercream layered on thick and in plentiful abundance. The only way frosting and fillings should be.

pumpkin whoopie pie

Pumpkin Whoopie Pies
Yield: 6

Pumpkin Whoopie Pies

Prep Time 20 minutes
Cook Time 12 minutes
Total Time 32 minutes

Soft and tender pumpkin cookies with a thick layer of sweet buttercream sandwiched between them will make you scream Whoopie for one of these fun pies. They're easy and fast to make, moist, and rich.

Ingredients

For the Cookies

  • 1 cup light brown sugar, packed
  • 1/2 cup canola or vegetable oil
  • 3/4 cup pumpkin puree
  • 1 large egg
  • 1 1/2 teaspoons vanilla extract
  • 1 teaspoon cinnamon
  • 1 teaspoon ground ginger
  • 1/2 teaspoon pumpkin pie spice
  • 1/4 teaspoon ground cloves
  • 1/4 teaspoon allspice
  • 1/2 teaspoon salt, optional and to taste
  • 1 1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon baking soda

For the Buttercream Filling

  • 2 tablespoons milk
  • 1 teaspoon vanilla extract
  • 2 cups powdered sugar, sifted and divided
  • 1/2 cup unsalted butter, softened

Instructions

  1. For the Cookies - Preheat oven to 325°F and line two baking sheets with Silpat liners or parchment paper; set aside. In a large mixing bowl, combine first 11 ingredients, up to the salt, and whisk until smooth. Add the remaining ingredients, and mix until just combined; don’t overmix. Batter will be soft and runny.
  2. Using a one-quarter cup measure, scoop the batter onto prepared baking sheets, six round mounds of batter per sheet; this may also be done with a pastry bag if preferred.
  3. Bake for about 12 to 14 minutes, or until tops have set. Cookies will be very soft and may look underdone, but firm up as they cool. Allow cookies to cool on baking sheets for at least 10 minutes before moving them to rack to finish cooling. Allow cookies to cool completely before filling and sandwiching them together. While they cool, make the filling.
  4. For the Buttercream Filling - To the bowl of a stand mixer fitted with a whisk attachment, combine the milk, vanilla extract, and 1 cup of the powdered sugar, then mix on high speed until the mixture is creamy and light. Add butter and remaining cup of sugar, and whip on high speed until very light, about 8 to 10 minutes.
  5. Apply a generous dollop of frosting to 6 of the cookies. Sandwich them together with the remaining unfrosted 6 cookies, creating 6 whoopie pies. Whoopie pies are best fresh, but extras may be stored airtight in the refrigerator (due to the buttercream) for about 3 days. If you prefer to keep them at room temperature, the frosting may be made with 1/4 cup vegetable shortening instead of butter.

Nutrition Information:

Yield:

6

Serving Size:

1

Amount Per Serving: Calories: 701Total Fat: 35gSaturated Fat: 11gTrans Fat: 0gUnsaturated Fat: 22gCholesterol: 72mgSodium: 350mgCarbohydrates: 94gFiber: 2gSugar: 67gProtein: 5g

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Pumpkin Banana Bread with Browned Butter Cream Cheese Frosting – This bread is a mixture of both pumpkin and banana flavors whereas the above cake is more robustly pumpkin-flavored. Depending on the flavor profile you want, they’re both moist, dense, pumpkiny, and you can’t go wrong with either

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All Pumpkin Recipes here

Have you ever made whoopie pies?

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