Pumpkin Whoopie Pies with Cinnamon Cream Cheese Filling

I have never been a big fan of pumpkin. I don’t fancy a pumpkin pie, pumpkin soup, a pumpkin cheesecake, or even a pumpkin bread. But a pumpkin whoopie pie? Those, I have to say, I kind of really love. Whoopie pies are hands-down one of my favorite things. I adore the ratio of filling (ie: frosting) to pie (ie: cake). I love the size, the portability, and the easy prep. When I worked at the bakery, we made a lot of whoopie pies. Back then (yes, this was about 100 years ago) whoopie pies were just beginning their comeback (although, in my mind, they were never gone) and Baked offered a variety of flavors (as they still do). Chocolate whoopie pies were, of course, my favorite, but I have to say the pumpkin ones totally won me over.

The lightly spiced, super moist cakes, filled with cream cheese frosting, made me reevaluate pumpkin altogether. Okay, “reevaluate” might be a stretch (I wasn’t running off to bake a pumpkin cheesecake, or anything brazen like that), but it certainly got me making pumpkin whoopie pies at home on a relatively frequent basis. I made them for Thanksgiving and xmas cookie swaps. I brought them to dinner parties and served them instead of cake for a friend’s winter bday. And I always used the baked recipe, the one we worked from in the bakery. And the whoopie pie recipe memorialized in  Matt and Nato’s first book. Until now, that is.

Cut to a few weeks ago, when I was all set to make chocolate whoopie pies for the taste testers’ school harvest festival, when the 12 year old tester asked if I could make pumpkin ones instead. At first I balked (I love the guy, but my thing for chocolate whoopies is no joke). But then, three things: I’m a sucker for a kid with a specific dessert request, I liked the prospect of making something seasonal (I was baking them for a harvest festival, no less) and I always love the opportunity to develop my own recipe for an old favorite.

Pumpkin whoopie pie recipe research immediately ensued. I knew the Baked recipe backwards and forwards and used it as my jumping off point. However, I quickly surmised that many/all of the recipes for pumpkin whoopies that I stumbled/jumped upon deviated in only the tiniest of ways from Baked’s. I spent some time, despite my initial finding, searching for recipes that differed, and went to work on my own. I amped up the leavening (I like a tall whoop) and the spices in mine, decided on a combo of granulated and brown sugar, added a yolk for moisture, and extra vanilla, to enhance all those lovely pumpkin-y flavors that said whoops had taught me to embrace. And for good measure, I spiced up my cream cheese frosting with a generous teaspoonful of cinnamon. The resulting pies were a huge hit at the festival, provided me with many a mom-point, and made me feel oh so seasonal. In a good way.

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4.50 from 2 votes

Pumpkin Whoopie Pies With Cinnamon Cream Cheese Filling

Recipe Author Jessie Sheehan

Course Dessert

Cuisine Pie

Ingredients

For the whoopie pies

• 3 cups all-purpose flour
• 1 Tbsp cinnamon
• 1 1/4 tsp baking powder
• 1 1/4 tsp baking soda
• 1 tsp salt
• 1 tsp nutmeg
• 1/2 tsp cloves
• 1/4 tsp white pepper
• 1 cup vegetable oil
• 1 1/2 cups light brown sugar
• 1/2 cup granulated sugar
• 2 tsp pure vanilla extract
• 2 eggs
• 1 yolk
• 3 scant cups of pumpkin puree from about 1 1/2 15 ounce cans

For the Filling

• 1 stick of unsalted butter room temp
• 1 eight ounce package of cream cheese room temp
• 1 Tbsp pure vanilla extract
• 2 1/2 to 3 1/2 cups confectioners' sugar sifted
• 1/8 tsp salt
• 1 tsp cinnamon

Instructions

To Make the Whoopie Pies

• In a medium bowl, whisk together the flour, cinnamon, leavenings, salt, nutmeg, cloves and white pepper.
• In a large bowl, combine the oil, sugars, and vanilla and whisk to combine. Add the eggs, yolk, and pumpkin, and whisk again. Add the dry ingredients and gently fold them into the wet, mixing just until the dry disappears. Cover the bowl with plastic wrap and place in the fridge for about an hour.
• Preheat the oven to 350-degrees. Line two baking sheets with parchment (or silicon baking mats). Using a small 1 1/2 tablespoon cookie scoop or measuring spoons, scoop the batter on to the pans.
• 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, cakey, and lightly pressing with your finger does not leave an indent. Do not over bake. Let the pies cool on the pans while you make the filling.

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.
• Place the the confectioners' sugar, salt and cinnamon in 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 thoroughly until combined after each addition. Once all of the sugar has been added, increase the speed of the mixer to medium or medium high, and beat the mixture til smooth. Do not over mix or the frosting will lose structure.
• Turn half of the whoopie pies over and using the same scoop, place about 1 tablespoon and a half of frosting on each one. top each one with another pie. consume immediately, or refrigerate until you are ready to do so.