The crisp air and colorful leaves of fall are the perfect backdrop for baking something a little nostalgic and a lot delicious — Chocolate Pumpkin Whoopie Pies. These pillowy-soft chocolate cakes sandwich a dreamy, spiced pumpkin buttercream that tastes like a hug from autumn itself.
Whether you make them with a gluten-free boxed cake mix or from scratch, they come together with ease and are ideal for sharing at gatherings, gifting to neighbors, or simply indulging in on a cozy afternoon. Wholesome ingredients, warm spices, and the joy of a classic treat reinvented — these whoopie pies are destined to become your new seasonal favorite.
Full recipe:
Ingredients:
For the Little Cakes:
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1 cup all-purpose flour (or gluten-free blend)
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1/4 cup cocoa powder
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1/2 cup granulated sugar
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1/2 teaspoon baking soda
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1/2 teaspoon kosher salt
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1/2 cup buttermilk, at room temperature
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1/4 cup unsalted butter, softened
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1 large egg
For the Pumpkin Buttercream Filling:
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1 1/2 cups powdered sugar, sifted
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1/2 cup unsalted butter, softened
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1/4 cup pumpkin puree
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1/8 teaspoon cinnamon
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1/8 teaspoon nutmeg
Directions:
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Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper.
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In a bowl, sift together flour, cocoa powder, sugar, baking soda, and salt.
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Add buttermilk, softened butter, and egg to the dry ingredients.
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Mix slowly with a hand mixer, increasing to medium speed until just smooth—do not overmix.
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Scoop the batter (about 2 tablespoons per cake) onto the baking sheet, spacing them 3 inches apart.
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Bake in batches for 10–14 minutes until the cakes bounce back to the touch.
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Let cakes cool on the sheet before transferring to a wire rack to cool completely.
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Meanwhile, beat together powdered sugar, butter, pumpkin puree, cinnamon, and nutmeg until smooth. Chill until ready to use.
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Pipe or scoop the filling onto half of the cooled cakes, then top with the remaining halves.
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Chill assembled whoopie pies in the fridge for 15–30 minutes before serving.
Prep Time: 10 minutes | Cooking Time: 15 minutes | Total Time: 55 minutes
Kcal: 56 kcal | Servings: 10 servings
What Makes Whoopie Pies So Special?
The whoopie pie may look like a cookie sandwich at first glance, but it’s so much more. The texture is soft and cake-like, offering a gentle bite that crumbles just enough to hold a luscious filling without falling apart. This delightful treat strikes a balance between comfort and elegance, making it beloved by kids and adults alike. Traditionally filled with a marshmallow cream, modern whoopie pies have evolved to include buttercreams and flavored fillings, and this chocolate pumpkin version is the perfect example of such innovation.
In this variation, moist chocolate cakes serve as the “bread,” while a velvety pumpkin buttercream brings in a seasonal twist. It’s a match made in autumn heaven. The richness of chocolate contrasts beautifully with the warm spiciness of cinnamon and nutmeg in the filling, making each bite layered and satisfying.
The History Behind the Whoopie Pie
Understanding the heritage of whoopie pies adds a layer of cultural appreciation to this already beloved dessert. Although there is a bit of controversy over their exact origins, most stories trace their roots to the northeastern United States. Both Pennsylvania and Maine claim to be the birthplace of whoopie pies, with strong traditions rooted in Amish and New England culture.
One of the most charming legends surrounding whoopie pies comes from Amish farm culture. It’s said that Amish women would bake them using leftover cake batter and pack them in their husband’s lunchboxes. Upon discovering the treat, the farmers would reportedly exclaim “Whoopie!” — hence, the dessert’s whimsical name. Regardless of where they truly originated, whoopie pies have made a mark on American baking culture, and their adaptability has allowed them to be reinvented time and again.
Modern Twists and Variations
Today’s whoopie pies are more than just the sum of cake and cream. They are canvases for creativity. You’ll find them in a rainbow of flavors: red velvet, peanut butter, gingerbread, lemon… the list goes on. But there’s something uniquely satisfying about the marriage of chocolate and pumpkin, particularly when the filling is infused with warm spices that evoke the essence of fall.
In this version, pumpkin puree is whipped into a creamy butter base with cinnamon and nutmeg for depth and character. The result is a smooth, flavorful filling that’s not too sweet and perfectly complements the dark chocolate exterior. These additions are not only flavorful but also serve to distinguish this variation from the more common iterations found at bakeries or grocery stores.
Why Chocolate and Pumpkin Work So Well Together
While chocolate and pumpkin might not seem like an obvious pairing, their chemistry in baking is undeniable. Chocolate offers a richness that grounds the light, earthy tones of pumpkin. The spices commonly paired with pumpkin—cinnamon, nutmeg, clove—act as bridges, drawing out the deeper notes in cocoa and softening any bitterness. This duo brings out the best in each other, creating a dessert experience that is complex without being complicated.
From a texture perspective, the softness of pumpkin puree also contributes moisture to fillings and batters, making cakes extra tender. When nestled between two fluffy chocolate domes, the pumpkin-spice filling provides not only flavor but a pleasing contrast in mouthfeel. It’s creamy and dense where the cake is light and spongy. Every element has a role to play, and when brought together, they create a harmony that feels festive, comforting, and luxurious all at once.
Gluten-Free and Boxed Mix Options
One of the best things about this recipe is its flexibility. For those looking to save time or simplify the baking process, it can easily be made using a gluten-free boxed chocolate cake mix. This approach ensures that the recipe remains accessible to a wide range of bakers, from beginners to pros, and also accommodates those with gluten sensitivities.
But don’t be fooled by the use of a box mix—these whoopie pies don’t taste like a shortcut. The quality of boxed baking products has improved significantly in recent years, especially from organic and natural brands, many of which are featured in this recipe. When paired with a homemade spiced pumpkin filling, the result tastes fully artisanal.
Alternatively, for those who prefer baking from scratch, a traditional flour-cocoa-sugar base creates a more tailored experience. The from-scratch version gives the baker complete control over texture, sweetness, and richness. It’s perfect for those who enjoy the process of measuring, mixing, and customizing every step of the recipe.
Tips for Assembling the Perfect Whoopie Pie
While the ingredients and flavor combinations are crucial, the assembly process can make or break a whoopie pie. The key to success is ensuring both the cakes and the filling are the right temperature. Cakes should be fully cooled to prevent the filling from melting and becoming runny. A chilled filling is easier to pipe or scoop and helps maintain structure, especially when storing or transporting the pies.
Using a piping bag with a large tip provides cleaner and more consistent results than using a spoon. This method allows for an even distribution of filling without over-handling the cakes. Once assembled, a brief chill in the refrigerator helps the pies set, making them easier to store and even more enjoyable to eat.
Make-Ahead and Storage Options
Another perk of this recipe is its ability to be prepared in advance. Both the chocolate cakes and the pumpkin filling can be made up to two days ahead and stored separately in the refrigerator. When stored properly—ideally separated with parchment or wax paper—the components retain their texture and flavor until ready to assemble.
Once assembled, the whoopie pies keep well in the refrigerator for a few days, making them a perfect make-ahead dessert for parties, gatherings, or special occasions. The slightly chilled filling gives a nice bite and holds its shape beautifully when served. If you plan to stack or transport them, placing parchment squares between each pie helps prevent sticking and smudging.
The Perfect Dessert for Any Autumn Occasion
Chocolate Pumpkin Whoopie Pies aren’t just a treat—they’re a seasonal statement. Whether you’re hosting a harvest dinner, attending a Halloween party, or simply enjoying a quiet fall afternoon with a cup of tea, these whoopie pies bring the warmth and spirit of autumn right to your plate. Their playful shape and handheld size make them approachable, while their rich, layered flavor makes them unforgettable.
They also make wonderful gifts. Wrapped in wax paper and twine, a few whoopie pies tucked into a box feel like a homemade gesture straight from the heart. They’re nostalgic without being old-fashioned and creative without being complicated. The best of all dessert worlds.
Conclusion: A New Fall Favorite
In the realm of seasonal desserts, Chocolate Pumpkin Whoopie Pies are a standout. They bring together nostalgic elements of American baking with modern flavor twists that elevate the experience. The contrast between soft chocolate cakes and creamy, spiced pumpkin filling makes for a bite that’s equal parts comfort and joy. Flexible enough to suit gluten-free diets and simple enough for novice bakers, they are both approachable and impressive.
These little cakes aren’t just for kids’ lunchboxes anymore—they’ve grown up into elegant treats perfect for the autumn months. So as you gather your spices and preheat your oven, know that what you’re baking is more than just dessert. You’re creating a moment, a memory, a celebration of the season.