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Pumpkin Whoopie Pies with a Whipped Cinnamon Filling

  • Author: Melissa Griffiths - Bless this Mess
  • Total Time: 1.5 hours
  • Yield: 2 dozen sandwich cookies 1x


Brace yourselves for bites of heaven -- these pumpkin whoopie pies with whipped cinnamon filling are the perfectly sweet and soft, cream-filled cookie sandwiches you need this fall... and probably year-round, too.


For the cookies:
  • 1/2 cup butter, softened
  • 1 1/4 cups granulated sugar
  • 2 eggs, at room temperature
  • 1 cup pumpkin puree
  • 1 teaspoon vanilla extract
  • 2 cups flour
  • 1 teaspoon baking powder
  • 1 teaspoon baking soda
  • 1 teaspoon ground cinnamon
  • 1/2 teaspoon salt
For the filling:
  • 1/2 cup salted butter, softened
  • 1/3 cup whipping cream, at room temperature
  • 1/2 teaspoon cinnamon
  • 1 teaspoon vanilla bean extract (or 1 teaspoon vanilla extract)
  • 2 1/2 to 3 cups powdered sugar


  1. Preheat the oven to 350 degrees F.
  2. In a large bowl, or the bowl of your stand mixer with the cookie paddle attached, beat the butter and sugar on medium speed until light in color and fluffy, about 3 minutes.
  3. Add the eggs, and mix to incorporate.
  4. Add the pumpkin and vanilla, and mix to combine.
  5. Sprinkle the flour over the top of the butter mixture, and then sprinkle the baking powder, soda, cinnamon, and salt over the flour. Mix until well incorporated, about a minute.
  6. Using a one-ounce scoop, scoop the batter onto a parchment lined baking sheet, spacing them 2 inches apart.
  7. Bake for 10 to 12 minutes, until the cookie springs back slightly when touched.
  8. For the filling: Use a stand mixer or electric hand mixer to beat the butter, whipping cream, cinnamon, and vanilla bean extract with the wire whisk attachment. Beat at medium-high speed until very light and fluffy, about 5 minutes.
  9. Add the powdered sugar, and beat for another 3 to 5 minutes. The filling will be very fluffy and a medium-thin consistency. If the icing is too thick, add a touch of cream and beat again. If it is too thin, add a little more powdered sugar and beat again.
  10. When the cookies have cooled, spread a tablespoon of filling onto flat side of one cookie; top with flat side of second cookie to make a sandwich. Repeat with remaining cookies and filling.
  11. Store in covered container.


  • Using a scoop for the cookie dough makes the cookies nice and round. If you don't have a scoop, just take a little time and use two spoons to transfer the dough to the baking sheet. The more uniform the scoops of dough, the prettier your cookies will be.
  • The cookies are delicious without the filling, too. My husband, who is not a cinnamon fan, liked the cookies plain and so did my kids.
  • Prep Time: 15 min
  • Cook Time: 8 min
  • Category: dessert
  • Method: bake
  • Cuisine: American

Keywords: whoopie pie, pumpkin pie, pumpkin cookie, cookie recipe, pumpkin dessert, dessert