Pumpkin Whoopie Pies: A Cozy Fall Concoction with a Twist

Pumpkin whoopie pies are a little nostalgic, a little playful. I love how the pumpkin adds moisture and a subtle sweetness that’s unlike any other cookie. They’re perfect for pumpkin season, when everything feels a little more cozy and intentional. Plus, making the filling from scratch transforms these from simple cookies to a real treat.

Why These Pumpkin Whoopie Pies Are a Staple

They’re a warm hug in pastry form, perfect for chilly afternoons. Baking these feels like a ritual, a slow savoring of fall’s quiet charm. Plus, they’re endlessly customizable—more spice, less sugar, a drizzle of dark chocolate. Every batch reminds me that simple ingredients, combined with care, make the sweetest memories.

Breaking Down the Pumpkin Pie Magic

  • Canned pumpkin: The star ingredient — adds moisture and a gentle sweetness. Use the plain variety, not spiced.
  • Brown sugar: Gives warmth and a molasses note, balancing the spices.
  • Cinnamon: The warm backbone, but feel free to add a pinch of nutmeg or ginger for depth.
  • Butter: Creamy, rich, helps the filling stay smooth. Swap with coconut oil for a dairy-free version.
  • Egg: Provides structure and stability to the cookie dough.
  • All-purpose flour: Keeps the cookies tender but sturdy enough to hold the filling.
  • Baking soda: Leavening agent that helps cookies rise just enough, giving a slight chew.

Tools of the Pumpkin Pie Trail

  • Mixing bowls: To combine dry and wet ingredients separately.
  • Electric mixer or whisk: To beat butter and sugar until fluffy.
  • Cookie scoop: To portion dough evenly.
  • Baking sheets: To hold the cookies during baking.
  • Wire rack: To cool cookies evenly.

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 of all-purpose flour, 1 tsp baking soda, 1/2 tsp salt, and 1 tsp cinnamon.

Step 3: In another bowl, beat 1/2 cup softened butter with 1 cup brown sugar until creamy. Add 1 cup pureed pumpkin and 1 large egg, mix well.

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

Step 5: Using a tablespoon or cookie scoop, dollop rounds onto prepared baking sheets, leaving space to spread.

Step 6: Bake for 12-15 minutes, edges should turn golden and a toothpick inserted in the center comes out clean.

Step 7: Cool the cookies on a wire rack for at least 15 minutes before filling.

Cooking Cues & Tips for Pumpkin Whoopie Pies

  • The cookies should be golden around the edges but soft inside.
  • If they spread too thin, chill the dough for 10 minutes before baking.
  • The filling should be smooth and spreadable, not runny.
  • Listen for a slight crackle when the cookies are done.

Troubleshooting Pumpkin Whoopie Pie Mishaps

  • Dough is too wet and spread excessively.? Incorporate a little more flour if the dough is too sticky.
  • Cookies spread into thin disks.? Chill dough for 10 minutes if cookies spread too much.
  • Over-baked or burnt edges.? Reduce oven temperature slightly if edges brown too fast.
  • Filling melts or slides off.? Let cookies cool completely before filling.

Pumpkin Whoopie Pies

Pumpkin whoopie pies are soft, moist cookies filled with a creamy pumpkin-flavored filling. The cookies are made with pumpkin puree, warm spices, and a hint of molasses, resulting in a tender, slightly chewy texture. Once assembled, they resemble small sandwiches, perfect for cozy fall afternoons.
Prep Time 15 minutes
Cook Time 15 minutes
Total Time 30 minutes
Servings: 12
Course: Main Course
Cuisine: American
Calories: 180

Ingredients
  

  • 1 1/2 cups all-purpose flour
  • 1 tsp baking soda
  • 1/2 tsp salt
  • 1 tsp cinnamon
  • 1/2 cup butter softened
  • 1 cup brown sugar
  • 1 cup pureed pumpkin plain, not spiced
  • 1 large egg
  • 1 cup unsalted butter for filling
  • 2 cups powdered sugar for filling
  • 1/2 tsp cinnamon for filling
  • 1/4 tsp nutmeg optional, for filling

Equipment

  • Mixing bowls
  • electric mixer or whisk
  • 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 well combined. This helps evenly distribute the spices and leavening agents.
  3. In another bowl, beat the softened butter and brown sugar with an electric mixer until the mixture is fluffy, light, and creamy, about 2-3 minutes. The sugar should be slightly dissolved, and the mixture should smell warm and inviting.
  4. Add the pureed pumpkin and egg to the butter mixture, beating until the ingredients are thoroughly combined and the mixture looks smooth and slightly thickened.
  5. Gradually add the dry ingredients to the wet mixture, mixing just until the flour is incorporated. The dough will be thick and slightly sticky, but scoopable.
  6. Using a cookie scoop or tablespoon, portion the dough onto the prepared baking sheets, leaving about 2 inches between each dollop to allow for spreading.
  7. Bake in the preheated oven for 12-15 minutes, until the edges turn golden and the tops are set. You’ll hear a gentle crackle when they are done.
  8. Remove the cookies from the oven and let them cool on the baking sheets for 5 minutes before transferring them to a wire rack to cool completely. This prevents them from breaking apart while still warm.
  9. While the cookies cool, prepare the filling by beating softened butter, powdered sugar, cinnamon, and nutmeg until smooth and fluffy. The filling should be creamy and easy to spread.
  10. Once the cookies are completely cooled, spread a generous dollop of filling on the flat side of one cookie, then sandwich with a second cookie to form a small sandwich.
  11. Repeat with the remaining cookies and filling. Serve these tender, flavorful pumpkin whoopie pies at room temperature and enjoy the cozy fall flavors.

Notes

Chill the dough for 10 minutes if the cookies spread too much during baking. For a dairy-free version, substitute coconut oil for butter in the dough and filling.
These pumpkin whoopie pies are best enjoyed slightly chilled, with that soft, chewy cookie melting into a sweet, spiced filling. They’re a reminder that baking can be a quiet act of kindness, especially when the air turns crisp and the leaves start to fall. Feel free to tweak the spices or add a touch of ginger or nutmeg—make it your own. Nothing beats biting into one of these with a cup of tea, feeling that warm spice hit your tongue.

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