Pumpkin Whoopie Pies

I haven’t had much pumpkin going on in the kitchen. Which feels strange since Fall is in full swing and there’s no better time of year to indulge in all things pumpkin. This needed to be remedied!

Saturday night we attended a Pie Social. Yup, a party with a pie theme. This was right up my alley! Being a bit of a pain in the ass, though, I couldn’t let things be and bake a regular ole Fall-themed pie, as instructed: I had to make a play on words (again) and make whoopie pies. Pumpkin ones, in fact, with a Maple Cream Cheese filling. Oooh, the filling. I could have taken a spoon to that and been quite happy!

These are very moist cookie/cakes. I worried a bit that they were under-baked when we finally feasted upon them, but nobody else complained. I highly recommend doing the toothpick test to be sure, as it’s hard to tell from how they look whether they’re baked enough. As long as there are no crumbs, you’re good to go. I imagine it would be quite difficult to over-bake these, so don’t worry about that.

Because of the high moisture content, they will get sticky the longer they sit out. Which is true of most whoopie pies I make. I usually wrap each pie individually with plastic wrap to keep them from sticking together (and to keep your hands cleaner when eating!). Then store them in the refrigerator to save the cream cheese filling. They seem to be less sticky this way, too.

The verdict? Amazing! Spicy, not too sweet, with a finger-licking frosting holding it all together. A fabulous treat for this time of year!

Pumpkin Whoopie Pies

adapted from Annie's Eats

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Prep Time 20 minutes mins

Cook Time 1 hour hr

Total Time 1 hour hr 20 minutes mins

Course Cookie

Servings 24

Ingredients

  

Maple Cream Cheese Filling

• ½ cup 8 Tablespoons unsalted butter, softened
• 8 ounces full-fat cream cheese softened
• 4 cups confectioner's sugar sifted
• 2 Tablespoons Grade B pure maple syrup
• 1 vanilla bean split and scraped

Pumpkin Cookies/Cakes

• 3 cups all-purpose flour
• 1 teaspoon kosher salt
• 1 teaspoon baking soda
• 1 teaspoon baking powder
• 2 Tablespoons cinnamon
• 1 teaspoon ground ginger
• 1/2 teaspoon ground nutmeg
• 1/4 teaspoon ground cloves
• 1/2 cup coconut oil
• 1/2 cup unsalted butter softened
• 1 cup granulated sugar
• 1 cup light brown sugar lightly packed
• 2 large cage free eggs
• 1 teaspoon vanilla bean paste
• 2 15- ounce cans pumpkin puree not pumpkin pie filling

Instructions

 

Maple Cream Cheese Filling

• In the bowl of a stand mixer fitted with the paddle attachment, beat the butter and cream cheese, beating for a couple minutes to mix them together.
• Add the powdered sugar, maple syrup, and vanilla bean caviar and slowly turn on the mixer, working your way up to medium speed.
• Beat for 2-3 minutes or until smooth (if you don't sift your confectioner's sugar, the filling will be lumpy like mine; proceed at your own risk).
• Transfer to a covered container and chill in the refrigerator until ready to use.

Pumpkin Cookies/Cakes

• Preheat oven to 350 degrees Fahrenheit. Get out 2 rimmed baking sheets and set aside.
• In a large mixing bowl, whisk together the flour, salt, baking soda, baking powder, cinnamon, ginger, nutmeg, and cloves. Set aside.
• In the bowl of a stand mixer fitted with the paddle attachment, beat the coconut oil and butter, mixing for 2-3 minutes to blend together.
• Cream the sugars into the butter/coconut oil mixture, beating until light and fluffy (3-4 minutes).
• Beat in the eggs one at a time, incorporating the first fully before adding the second.
• Stir in the vanilla bean paste.
• Add the flour mixture and pumpkin puree, mixing slowly until incorporated. Scrape the sides, stir a few more rounds, and then remove from the mixer.
• Portion out with a #40 cookie scoop onto the baking sheets. They will not spread a lot, so you can bake 12 at a time.
• Bake for 13-15 minutes, or until a toothpick inserted in the center comes out clean.
• Let sit on pan for 2 minutes before removing to wire racks to cool completely.

Assembly

• Once the cookie/cakes are completely cooled, you can transfer the filling to a pastry bag fitted with a circle tip and pipe on the flat side of one cookie, then apply the flat side of another to the top to make little sandwiches.
• If you're in a hurry, you can spread the filling on the flat side of one cookie with a butter knife, apply the flat side of another cookie, and make your sandwiches that way.
• Eat within 3 days.

Notes

If you'd like smoother tops, you can pipe out the batter instead of scooping it, smoothing the surface of any irregularities with a clean water-moistened finger, or wet the back of a spoon.