Gluten-free pumpkin whoopie pies with chocolate filling

Halloween’s coming, but don’t be afraid! Make these festive pumpkin whoopie pies with chocolate filling and all the kids will knock on your door for the best treats.

How do you feel about Halloween? People usually fall into one of two categories: the lovers and the haters. I would like to introduce a third category, right here. Today. This category is for people who might not absolutely love Halloween but are just in it for the food. I hereby name myself the president and founding member of this category. Who’s with me? Well, perhaps the nudge you need is these gluten-free pumpkin whoopie pies — with chocolate buttercream filling. Whoopie pies are not, oddly, pies in the traditional sense. They’re also not really cookies, since they’re so very soft and pillowy. Part of the fun of whoopie pies is dressing them up for different occasions. This Halloween, let’s make them with some intense pumpkin flavor.

Have you ever made your own pumpkin butter? Pumpkin butter is what those simple cans of pumpkin puree that are everywhere this time of year would be, if only they could. It has much less moisture than pumpkin puree, which makes it much more useful as a baking ingredient. And it’s so easy to make at home just by cooking down pumpkin puree with maple syrup and apple cider (see below for specific directions). If you do make your own, you’ll save yourself a bundle. Point of interest? Pumpkin butter has no actual butter in it. But these whoopie pies sure do!

Gluten-free pumpkin whoopie pies with chocolate filling recipe

Yields 14 whoopie pies

Ingredients:

Whoopie pies

• 4 ounces pumpkin butter (store-bought or homemade from directions below)
• 2 cups all-purpose gluten-free flour (use your favorite blend, or my go-to blend: 1 cup plus two tablespoons superfine white rice flour plus 7 tablespoons potato starch plus 4-1/2 tablespoons tapioca flour/starch)
• 1/2 teaspoon xanthan gum
• 3/4 teaspoon baking powder
• 1/4 teaspoon baking soda
• 1/2 teaspoon kosher salt
• 1-1/2 teaspoons pumpkin pie spice
• 4 tablespoons unsalted butter, at room temperature
• 2 tablespoons vegetable shortening
• 3/4 cup packed light brown sugar
• 1 large egg at room temperature, beaten
• 1 teaspoon pure vanilla extract
• 1/2 cup milk, at room temperature
• Orange gel food coloring, to desired color (optional)

Filling

• 16 tablespoons (224 g) unsalted butter, at room temperature
• 1/4 teaspoon kosher salt
• 1/2 cup Dutch-processed or natural cocoa powder
• 3 to 3-1/2 cups confectioners’ sugar
• Gluten-free chocolate sprinkles for decorating (optional)

Directions:

1. Preheat your oven to 325 degrees F. Line a large rimmed baking sheet with unbleached parchment paper and set it aside.
2. If you wish to make your own pumpkin butter, in a medium heavy-bottom stockpot, combine 1 (15 ounce) can of pumpkin puree with 3 tablespoons pure maple syrup and 4 fluid ounces apple cider or apple juice. Mix to combine and simmer on low heat until reduced by at least half. Allow to cool before using in this recipe.
3. First, make the whoopie pies. In a large bowl, place the flour blend, xanthan gum, baking powder, baking soda, salt and pumpkin pie spice, and whisk to combine well. Set the bowl aside. In a separate, large bowl, place the butter and vegetable shortening, and beat with a hand-held mixer until light and fluffy. Add the brown sugar, egg and vanilla, beating until well-combined after each addition. Add the pumpkin butter, and mix again to combine. Create a well in the center of the dry ingredients, and add wet mixture, and the milk, alternating between the two and mixing well in between additions. The batter should be light and fluffy. If desired, add the gel food coloring and mix again to combine until you reach the desired color.
4. Spoon the batter into a piping bag fitted with a 1/2 inch plain piping tip. Pipe 1-1/2-inch mounds of the whoopie pie batter on the prepared baking sheets about 2 inches apart from one another (they will spread as they bake). Flatten the mounds into about 1/2-inch thick disks with wet fingers. Place the baking sheet in the center of the preheated oven and bake until the tops spring back when pressed lightly with a fingertip (between 10 and 12 minutes). Remove from the oven and allow to cool completely before filling.
5. While the whoopie pie halves are cooling, make the filling. In a large bowl with a hand-held mixer (or with a stand mixer and the paddle attachment), beat the butter and salt on high speed until very light and fluffy. Add the cocoa powder and 3 cups of confectioners’ sugar, and beat on medium speed until the dry ingredients are absorbed into the butter. Turn up the speed to high, and continue to beat until light and fluffy. Scoop up a heaping tablespoon of the filling. If it doesn’t hold its shape, incorporate more confectioners’ sugar by the tablespoon until it does.
6. Once the pie halves are completely cool, match up halves of similar size and shape. Place about 2 tablespoons of filling on the underside of one cookie in each pair, and place the other cookie on top to close the pie. Press gently to force the filling right to the edges of the pies. Press the exposed frosting gently into the optional chocolate sprinkles, and shake off any excess. Serve immediately.

More gluten-free recipes

Gluten-free apple cider muffins
Mini gluten-free apple crisps
Gluten-free sour cream cheddar cheese muffins