Pumpkin Spice Whoopie Pies: Cookies Perfect for Halloween & Thanksgiving. Boo!
Are you one of those, like moi, that anticipates pumpkin treats season?: You’re in luck, we’ve got you covered—AGAIN!
Welcome to the Mountaintop Kitchen, where baked goodness fills the air every day. My best friend’s family started the Moon Pie craze out of Chattanooga, Tennessee, generations ago. If you’ve never had Moon Pies, you need to find some; they are yummy and super fun to eat. I felt like honoring that history with a related bake: Pumpkin Spice Whoopie Pies. These cookies were surely the inspiration behind MoonPie’s creation and great success.
At Mountaintop Kitchen, we embrace the flavors of fall with our Pumpkin Spice Whoopie Pies, a modern take on a classic treat that brings nostalgia and warmth to the holiday season. Originating in the northeastern U.S., particularly popular in Pennsylvania, whoopie pies have a long history of delighting dessert lovers with their pillowy, cake-like cookies and sweet, creamy filling. We’ve elevated this beloved treat by incorporating the quintessential autumn ingredient: pumpkin.
Pumpkin has become a seasonal favorite, especially as the cooler months approach. Its natural sweetness and moist texture combine beautifully with a warming blend of cinnamon, ginger, and cloves in our cookie dough. These fragrant spices, balanced with rich brown sugar and smooth pumpkin puree, create soft cookies that are moist, tender, and full of depth. The addition of baking powder and baking soda gives them a light, airy structure, perfect for sandwiching with our luscious filling.
The filling itself is a silky, sweet blend of shortening, butter, confectioners’ sugar, and a hint of vanilla or maple syrup. It’s fluffy and smooth, contrasting beautifully with the spiced cookies. Together, these elements form a whoopie pie that is equal parts indulgent and comforting—a true celebration of the holiday season’s most cherished flavors.
So don those aprons, let’s bake!
On Measuring Ingredients: My preferred method of measuring is weight by grams. Baking by volume rather than weight can lead to varied and unexpected results. Flour is especially problematic when measured by volume (sifted, not sifted, spooned, not spooned, fluffed or not … you get the point). Grams are always the same; they are your friend as a baker. King Arthur Baking Company’s Ingredients Weight Chart is helpful for converting recipe weights.
On Altitude Adjustments: Before measuring ingredients, preheating your oven, or setting your timer; it’s important to consider any necessary adjustments for baking at higher altitudes, which is generally considered to be 3,500ft and above. Most recipes are written for sea level up to 3,500ft. Take at look at our baking at High-Altitude Baking Adjustments page for guidance.
These tender, spiced pumpkin cookies are sandwiched together with a smooth and sweet vanilla cream filling, making them the perfect treat for fall.
Cookie Dough:
2 cups (424g) packed brown sugar
1 cup (198g) vegetable oil
1 ½ cups (340g) solid-pack pumpkin puree
2 large eggs
3 cups (360g) all-purpose flour
1 ½ tablespoons ground cinnamon
½ tablespoon ground ginger
½ tablespoon ground cloves
1 teaspoon salt
1 teaspoon baking powder
1 teaspoon baking soda
1 teaspoon vanilla extract
Whoopie Pie Filling:
1 egg white
2 tablespoons (30g) milk
1 teaspoon vanilla extract
2 cups (227g) confectioners’ sugar, divided
½ cup shortening + ¼ butter (144g total)
For a thinker, more stable filling, use all shortening. At Mountaintop Kitchen, we prefer the addition of butter to the filling for a creamy and buttery taste and texture.
1. Preheat the oven: Preheat the oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone mats.
2. Make the cookie dough: In a large bowl, whisk together the brown sugar, vegetable oil, pumpkin puree, and eggs until smooth and well combined.
In a separate bowl, whisk together the flour, cinnamon, ginger, cloves, salt, baking powder, and baking soda (or use homemade or store-bought pumpkin spice)
Gradually add the dry ingredients to the wet mixture, stirring until just combined. Stir in the vanilla extract.
3. Bake the cookies: Scoop the dough onto the prepared baking sheets, using about 1 tablespoon of dough per cookie. Leave about 2 inches (5 cm) between each cookie to allow for spreading. Optionally use a piping bag and tip with a large round opening for greater control and perfectly round cookies (as was done for this recipe).
Bake the cookies for 12–14 minutes, until the edges are set and a toothpick inserted into the center comes out clean.
Remove the cookies from the oven and allow them to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.
4. Prepare the filling: In a large mixing bowl, beat the egg white, milk, and vanilla extract until frothy. Gradually beat in 1 cup (113g) of the confectioners’ sugar.
Add the shortening/butter and the remaining 1 cup (113g) of confectioners’ sugar. Beat until the filling is light, fluffy, and smooth.
5. Assemble the whoopie pies: Once the cookies are completely cool, spread or pipe a generous amount of the filling onto the flat side of half the cookies. We used a piping bag and a Wilton 1M piping tip for extra flair.
Top with the remaining cookies to form sandwiches.
6. Store: Store the whoopie pies in an airtight container at room temperature for up to 3 days, or refrigerate for up to a week.
Yield: About 24-36 whoopie pies depending on size.
These classic pumpkin whoopie pies are the perfect combination of soft, spiced cookies and a sweet, creamy filling. Enjoy!
Equipment (Disclosure: Items below include affiliate links with Amazon USA. You pay the regular price, and I get a small commission.) I only recommend products that I own myself and know to be excellent quality. I often get asked on social media sites about my kitchen tools, so here are most of them used to make this recipe.
Mixing bowls (I like this oven-proof glass set of 10 for mixing and portioning out ingredients.)
Stand mixer (This dough can be mixed by hand, but a stand mixer ensures consistency.)
Cordless electric hand mixer (This is a handy mixer for these smaller bakes.)
Kitchen scale (Ingredients should be weighed rather than relying on volume.)
Oven thermometer (All ovens need calibration, an in-oven thermometer is essential.)
Silicon oven mitts (I’ve burned my hands too many times with cloth mitts.)
Sauce pan (This is a versatile pan that works on all cooktops.)
Parchment paper (Also check Costco.)
Whisk (This is a standard for combining dry ingredients.)
Silicone spatula set (These are great at high temperatures.)
Wire cooling rack (Every kitchen needs at least two.)
USA cookie sheet pans (Get the best you can afford; much worth it! This 3-piece set won’t disappoint.)
Piping bags (I like the control that these medium-sized piping bags provide.)
Piping tip set (This is a nice set for many applications. We use the Wilton 1M tip to pipe the dough onto silicone mats.)
Thank you for stopping by the Mountaintop Kitchen today. Please subscribe if you haven’t already (It’s free to do so.), share the post with a friend, and bake these whoopie pies!
—Frank, The Mountaintop Baker
Precursors to Oreos or alfajores? Whatever, they look positively, absolutely delish.