This pumpkin whoopie pies recipe is one of those seasonal treats that instantly signals autumn and holiday baking in our house. I first made these on a chilly November afternoon when I wanted something beyond the usual pumpkin loaf. The aroma of pumpkin spice and brown sugar pulled everyone into the kitchen—my kids declared them unofficial holiday cookies at first bite. What makes these so special is the balance: tender, cake-like pumpkin rounds with a rich, tangy cream cheese filling that softens the sweetness and keeps every bite interesting.

They are forgiving to make, perfect for a cookie swap, and hold up beautifully on a plate or in a gift box. I love how the texture is soft and pillowy rather than crunchy, and the filling pipes on thick so each sandwich feels indulgent without being overwhelmingly sweet. Over the years I have experimented with different spices and cream cheese ratios; this version captures the best family-approved balance between spice, sweetness, and creamy tang. Whether you’re baking for a holiday, a school event, or an after-dinner treat, these are the kind of desserts that prompt second helpings and recipe requests.

Ingredients

• Light brown sugar: 1 3/4 cups packed. Adds moisture and a deep caramel flavor. I prefer darker light brown for richer taste; pack it into the measuring cup for accuracy.
• Salted butter: 1 cup (2 sticks), softened. Use real butter for best flavor; salted keeps the sweetness balanced but reduce added salt if using unsalted butter.
• Large eggs: 2. Room temperature eggs incorporate more easily and give a lighter crumb.
• Pumpkin puree: 15 ounces (about 2 cups). Use 100% pumpkin puree, not pumpkin pie filling; it has no added sugar or spices.
• All-purpose flour: 2 1/2 cups. Spoon and level into the cup to avoid packing too much flour and ending up with dense cookies.
• Pumpkin pie spice: 2 tablespoons. Make your own blend with cinnamon, ginger, nutmeg, allspice, and cloves for the most vibrant flavor.
• Baking soda and baking powder: 1 teaspoon baking soda and 3/4 teaspoon baking powder. Together they provide lift and a tender, cake-like texture.
• For the filling — salted butter: 3/4 cup softened. Use the same butter as in the cookies to unify the flavor.
• Cream cheese: 8 ounces softened. Full-fat yields the creamiest, most stable filling.
• Powdered sugar: 4 1/2 cups sifted. Sifting prevents lumps and gives a silky texture to the filling.
• Heavy cream: 2 tablespoons. Adds lightness; adjust slightly for pipeability.
• Salt: 1/2 teaspoon. Enhances flavor and balances the sweetness.

Instructions

Preheat and prepare pans: Preheat the oven to 3506F. Line two sheet pans with parchment paper and set aside. Proper lining prevents sticking and helps the bottoms brown evenly. If you only have one sheet pan, bake in batches and allow pans to cool between bakes to maintain even heat. Cream butter and sugar: In a stand mixer or with a hand mixer, beat the light brown sugar and softened butter together until creamy and fluffy, about 2-3 minutes on medium speed. Scrape the bowl frequently so no pockets of butter remain. This step traps air and contributes to the cookie's tender lift. Add eggs and pumpkin: Add the eggs one at a time, mixing well after each addition and scraping the bowl. Then beat in the pumpkin puree until evenly incorporated. The mixture should look smooth and homogenous; do not overmix once the flour goes in or the crumb will become tough. Combine dry ingredients: In a separate large bowl, whisk together the all-purpose flour, pumpkin pie spice, baking soda, and baking powder. Whisking ensures the leaveners are evenly distributed for consistent rise in every cookie. Mix batter and portion: Fold or beat the flour mixture into the wet ingredients on low speed until just combined. Use a medium cookie scoop (about 1.5 tablespoons) to portion mounds of batter onto the prepared pans, leaving about 2 inches between each to allow for spreading. Bake and cool: Bake for 12 to 15 minutes, or until the centers are set and the edges look slightly springy. Rotate pans halfway through if your oven runs hot. Remove from oven and let the cookies cool completely on the pan for 5 minutes, then transfer to a cooling rack to finish cooling. Make the filling: Beat the softened butter and cream cheese together until smooth. Gradually add the sifted powdered sugar, then beat in the heavy cream and salt until light and fluffy, about 4 to 5 minutes. Taste for balance — add a pinch more salt if the filling seems too sweet. Assemble sandwiches: Flip one cookie over and pipe or spoon about 2 tablespoons of filling onto the flat side. Top with a second cookie and gently press to spread the filling to the edges. Chill assembled whoopie pies for 15 minutes to set the filling if needed.

Storage Tips

Store unfilled cookie rounds in an airtight container at room temperature for up to 48 hours to preserve softness. Once filled, refrigeration is best if you plan to keep them more than a day; place parchment between layers to prevent sticking. For long-term storage, freeze assembled sandwiches individually on a tray until firm, then transfer to a freezer bag and label with the date — they keep well for up to 3 months. To serve from frozen, thaw in the refrigerator overnight to avoid sogginess and bring to room temperature before serving for optimal flavor.

Ingredient Substitutions

If you need dairy-free options, swap butter with a vegan baking stick and use a dairy-free cream cheese alternative for the filling, though texture will be slightly softer. For a lower-sugar filling, reduce powdered sugar by 1/2 cup and increase cream by 1 tablespoon to maintain spreadability. To make them gluten-free, replace the all-purpose flour with a 1-to-1 gluten-free blend that contains xanthan gum; expect a slightly different crumb. For extra warmth, increase the pumpkin pie spice by 1/2 teaspoon or add a pinch of ground cardamom for floral notes.

Serving Suggestions

Serve warm or at room temperature alongside a cup of spiced latte or chai. For a holiday platter, dust with a light sprinkle of cinnamon or finely chopped toasted pecans for crunch. They are also excellent paired with vanilla ice cream; halve one whoopie pie and sandwich a small scoop for an indulgent dessert. For gift boxes, stack in layers separated by parchment and finish with twine and a sprig of rosemary for a rustic touch.

Cultural Background

Whoopie pies are a classic American treat with debated regional origins, often linked to New England and Pennsylvania Dutch traditions. Historically, they were a portable, celebratory confection; bakers filled cake-like rounds with sweet fillings for farmworkers to take to the fields. The pumpkin variation is a seasonal American twist that leverages autumn harvest flavors, combining the soft cake texture of the original with the warming spices associated with pumpkin pie.

Seasonal Adaptations

In winter, swap pumpkin for mashed sweet potato and add a touch of molasses for deeper flavor. For spring, use lemon curd in place of cream cheese for a bright contrast. Around Thanksgiving, add a teaspoon of maple extract to the filling and sprinkle flaky sea salt on top to enhance the nutty, caramel notes. Simple spice swaps and topping choices help tailor these to any seasonal menu.

Meal Prep Tips

Make the cookie rounds and filling a day ahead; store them separately and assemble on the day you serve to maintain the freshest texture. If piping the filling, chill it briefly until firm enough to hold shape but still soft enough to squeeze. Pack completed whoopie pies in single layers for transport with parchment between layers to prevent smudging. For larger events, double the batch and use an extra mixer bowl to keep assembly moving smoothly.

These pumpkin whoopie pies are a cozy, crowd-pleasing addition to your seasonal baking rotation. They are simple enough for a weeknight bake and special enough for holiday entertaining — bake a batch, share with loved ones, and make them your own with the variations suggested above.