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 tender, cookie-like treats with a warm, spicy pumpkin flavor and a creamy filling. The baking process creates soft, cracked tops with a moist interior, perfect for autumn gatherings. These homemade cookies are forgiving and bring cozy fall nostalgia with every bite.
Prep Time 15 minutes
Cook Time 15 minutes
Total Time 30 minutes
Servings: 12
Course: Main Course
Cuisine: American
Calories: 180

Ingredients
  

  • 1.5 cups all-purpose flour
  • 1 teaspoon baking soda
  • 0.5 teaspoon salt
  • 1 teaspoon cinnamon
  • 0.5 cup unsalted butter softened
  • 0.5 cup brown sugar
  • 0.5 cup maple syrup
  • 1 cup canned pumpkin
  • 1 teaspoon vanilla extract
  • 8 oz cream cheese softened

Equipment

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

Method
 

  1. Preheat your oven to 180°C (350°F) and line two baking sheets with parchment paper.
  2. In a large bowl, whisk together the flour, baking soda, salt, and cinnamon until evenly combined.
  3. In another bowl, beat the softened butter, brown sugar, and maple syrup with a hand mixer until the mixture is fluffy and light, about 2-3 minutes. You’ll notice it becomes pale and airy.
  4. Mix in the canned pumpkin and vanilla extract until the batter is smooth and well combined, with a slightly thick, moist texture.
  5. Gradually add the dry ingredients into the wet mixture, folding gently until just combined. The dough should be thick but scoopable, similar to soft cookie dough.
  6. Using a cookie scoop, drop spoonfuls of batter onto the prepared baking sheets, spacing them about 2 inches apart. Flatten each slightly if desired.
  7. Bake in the preheated oven for 12-15 minutes, or until the tops crack slightly and edges turn a light golden brown. You’ll hear a gentle sizzle as they bake.
  8. Let the cookies cool on the baking sheet for about 5 minutes, then transfer them to a wire rack to cool completely. They should feel firm but tender to the touch.
  9. Meanwhile, beat the softened cream cheese until smooth and creamy. You can add a little powdered sugar if you prefer a sweeter filling, but this classic tangy cream is perfect as is.
  10. Once the cookies are completely cooled, spread or pipe a generous dollop of the cream cheese filling onto the flat side of one cookie, then top with another cookie to form a sandwich.
  11. Press gently to spread the filling to the edges, then serve these cozy pumpkin whoopie pies and enjoy their soft, spicy, creamy goodness.

Notes

For best results, chill the filled pies for 30 minutes to help the filling set. These treats are perfect for fall gatherings or a cozy afternoon tea.
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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Recipe Rating




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, cookie-like treats with a tender crumb, featuring a spiced pumpkin-flavored cake paired with a creamy filling. The baking process involves mixing simple ingredients, shaping, and baking until slightly cracked on top. The final result is a cozy, nostalgic dessert perfect for autumn celebrations.
Prep Time 20 minutes
Cook Time 15 minutes
Total Time 35 minutes
Servings: 12
Course: Main Course
Cuisine: American
Calories: 220

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 the pies

Equipment

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

Method
 

  1. Preheat your oven to 180°C (350°F) and line two baking sheets with parchment paper.
  2. In a large bowl, whisk together the flour, baking soda, salt, and cinnamon until evenly combined. Set aside.
  3. In another bowl, beat the softened butter, brown sugar, and maple syrup with a hand mixer until the mixture is light and fluffy, about 2-3 minutes. You should see a pale, airy texture and a sweet aroma.
  4. Mix in the canned pumpkin and vanilla extract until the batter is smooth and well combined, with a slightly thick but scoopable consistency.
  5. Gradually add the dry ingredients to the wet mixture, folding gently until just combined. The batter should be thick but hold its shape when scooped.
  6. Using a cookie scoop, dollop the batter onto the prepared baking sheets, spacing about 2 inches apart. You should get about 12 cookies per sheet.
  7. Bake in the preheated oven for 12-15 minutes, until the edges are lightly golden and the tops crack slightly. You’ll hear a gentle bubbling sound as they bake.
  8. Remove the cookies from the oven and let them cool on the baking sheet for about 5 minutes. Then transfer them to a wire rack to cool completely, about 20 minutes. They should be firm but still tender.
  9. Once cooled, spread or pipe the creamy filling onto the flat side of one cookie and gently press another cookie on top to create a sandwich. Repeat with remaining cookies.
  10. Serve the pumpkin whoopie pies slightly chilled or at room temperature, enjoying the soft, spiced cake with the tangy, creamy filling. They’re perfect for cozy fall gatherings or a sweet treat anytime.

Notes

For extra flavor, sprinkle a pinch of cinnamon on the filling or dust with powdered sugar before serving.
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.

Leave a Comment

Recipe Rating