Pumpkin Whoopie Pies: A Nostalgic Fall Treat with a Twist

Pumpkin whoopie pies aren’t just for Halloween—they’re a reminder of autumn’s quiet magic. I love how the spicy, smoky pumpkin flavor pairs with a sweet, creamy filling, making each bite a little celebration. This recipe is about embracing imperfection and enjoying the simple joy of baking from scratch.

Why I Keep Baking These Pumpkin Pies

They’re simple but deeply satisfying—each batch feels like a small, imperfect gift. The smell alone, smoky and sweet, fills my house with fall nostalgia. Plus, they’re forgiving—mess up the measurements, and they still turn out cozy and delicious.

What’s Inside These Little Clouds?

  • Canned pumpkin: Adds moisture, a gentle earthiness, and seasonal color. Swap with sweet potato for a slightly different sweetness.
  • Brown sugar: Gives a deep caramel note and moisture. White sugar can be used but loses some richness.
  • Maple syrup: Sweetens naturally with a smoky, robust flavor. Honey can substitute, but it’s milder.
  • Cinnamon and spices: Warm, aromatic, essential for that cozy fall scent. Nutmeg or ginger can deepen the spice.
  • Butter: Creamy and rich, it lends tenderness. Vegan butter works well here.
  • All-purpose flour: Foundation of structure, ensures a soft crumb. Whole wheat offers a nuttier flavor.
  • Cream cheese or buttercream filling: Creamy, tangy, balances sweetness. Use vegan cream cheese for dairy-free.

Tools of the Trade for Pumpkin Whoopie Pies

  • Mixing bowls: For combining wet and dry ingredients without mess.
  • Whisk and hand mixer: To beat the butter and sugar until fluffy, and blend ingredients smoothly.
  • Cookie scoop: Ensures uniform cookies for even baking.
  • Baking sheets and parchment paper: Prevent sticking and easy removal of baked cookies.
  • Wire rack: Cooling baked cookies evenly and preventing sogginess.

Crafting the Perfect Pumpkin Whoopie Pie

Step 1: Preheat your oven to 180°C (350°F). Line two baking sheets with parchment paper.

Step 2: In a large bowl, whisk together 1 1/2 cups all-purpose flour, 1 teaspoon baking soda, 1/2 teaspoon salt, and 1 teaspoon cinnamon.

Step 3: In another bowl, beat 1/2 cup softened butter, 1/2 cup brown sugar, and 1/2 cup maple syrup until fluffy. Mix in 1 cup canned pumpkin and 1 teaspoon vanilla.

Step 4: Gradually add the dry ingredients to the wet, mixing just until combined. The batter should be thick but scoopable.

Step 5: Using a cookie scoop, dollop the batter onto the prepared sheets, about 2 inches apart. Bake for 12-15 minutes until edges are set and tops are slightly cracked.

Step 6: Let the cookies cool on the sheet for 5 minutes, then transfer to a wire rack. Cool completely before filling.

Cooking Checkpoints and Tips

  • The batter should be thick enough to hold its shape on the scoop, not runny.
  • Cookies should crack slightly on top and be lightly golden around the edges.
  • Filling should be creamy and hold its shape without oozing out.
  • Always cool the cookies completely before assembling to prevent melting the filling.

Common Mistakes and How to Fix Them

  • Cookies turn out dense and dry.? Use too much flour? Lighten your measurements with a spoon, then level off.
  • Cookies are hard and crumbly.? Overbake slightly? Remove cookies when edges are golden and centers are soft.
  • Filling oozes out and makes assembling messy.? Filling too runny? Chill it for 10-15 minutes before piping.
  • Cookies are pale and too soft.? Undercooked cookies? Bake a few minutes longer, until they crack on top.

Pumpkin Whoopie Pies

Pumpkin whoopie pies are soft, cake-like cookies with a warm, spicy aroma, filled with a creamy, tangy filling. The cookies are made by mixing pumpkin, spices, and flour, then baked until cracked and lightly golden. They are assembled with a generous layer of cream cheese or buttercream, creating a cozy fall treat with a melt-in-your-mouth texture.
Prep Time 15 minutes
Cook Time 15 minutes
Total Time 30 minutes
Servings: 12
Course: Main Course
Cuisine: American
Calories: 200

Ingredients
  

  • 1 1/2 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1 teaspoon cinnamon
  • 1/2 cup softened butter
  • 1/2 cup brown sugar
  • 1/2 cup maple syrup
  • 1 cup canned pumpkin
  • 1 teaspoon vanilla extract
  • 1 cup cream cheese or buttercream filling for filling

Equipment

  • Mixing bowls
  • Whisk or hand mixer
  • Cookie scoop
  • Baking sheets
  • Parchment paper
  • Wire Rack

Method
 

  1. Preheat your oven to 350°F (180°C) and line two baking sheets with parchment paper.
  2. In a large mixing bowl, whisk together the flour, baking soda, salt, and cinnamon until well combined. This creates a flavorful, spiced dry base.
  3. In another bowl, beat the softened butter, brown sugar, and maple syrup with a whisk or hand mixer until the mixture is fluffy and pale, about 2-3 minutes. This develops a light, airy texture and enhances sweetness.
  4. Mix in the canned pumpkin and vanilla extract until the batter is smooth, fragrant, and slightly thickened. The pumpkin adds moisture and a rich orange hue.
  5. Gradually fold the dry ingredients into the wet mixture just until combined. The batter should be thick but scoopable, with no streaks of flour remaining.
  6. Using a cookie scoop, portion the batter onto the prepared baking sheets, spacing each dollop about 2 inches apart. These will spread slightly during baking.
  7. Bake in the preheated oven for 12-15 minutes until the edges are lightly golden, and the tops crack slightly, signaling doneness.
  8. Remove the cookies from the oven and let them cool on the baking sheet for about 5 minutes to firm up, then transfer them to a wire rack to cool completely. This step prevents sogginess and makes them easier to fill.
  9. Once cooled, spread or pipe a generous layer of cream cheese or buttercream filling onto the flat side of one cookie, then top with a second cookie to form a sandwich.
  10. Repeat with remaining cookies and filling, then enjoy these cozy autumn treats that are perfect for sharing or savoring on their own.

Notes

Ensure cookies are completely cooled before filling to prevent the filling from melting. For a richer flavor, add a pinch of nutmeg or ginger to the dry ingredients. Chill the assembled pies for 30 minutes for easier handling.
This pumpkin whoopie pie recipe is a cozy, imperfect thing that brings back childhood memories of fall festivals and family desserts. It’s forgiving—overmix the batter, and it still works. Enjoy the process, and don’t rush the cooling; that’s when the flavors settle and the filling gets cozy inside. These aren’t polished pastries—just good, honest comfort in every bite.

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