Jack-O-Lantern Whoopie Pies | The Squeaky Mixer

Jack-O-Lantern Pumpkin Whoopie Pies

These are the BEST Pumpkin Whoopie Pies you’ll ever have. The texture is so moist, and fluffy, and pairs perfectly with the sweet, pillowy Cream Cheese Frosting. There is a perfect amount of spice, sweetness, and of course – the real star of the show, pumpkin.

Jack-O-Lantern Whoopie Pies | The Squeaky Mixer

How To Store Pumpkin Whoopie Pies

Once the Whoopie Pies have cooled completely and have been fully assembled, store them in an air tight container or large ziplock baggie and store in the fridge for up to one week or in the freezer for up to two months. That being said, Pumpkin Whoopie Pies are best enjoyed fresh, at room temperature so if you can, enjoy these right away and do your best to share 🙂

Jack-O-Lantern Whoopie Pies | The Squeaky Mixer

Scooping Pumpkin Whoopie Pies

Whatever tool you’re using to scoop the batter onto the prepared cookie sheets, do you best to ensure that each Whoopie Pie is getting the same amount of batter. This will ensure that matching up your Whoopie Pies down the road will be much easier and that the top and bottom Whoopie Pie shell will be the same size.

I recommend using a cookie scoop to achieve the same size Whoopie Pies. In a pinch you can also just use a regular spoon and scoop the batter one spoonful at a time.

Jack-O-Lantern Whoopie Pies | The Squeaky Mixer
Jack-O-Lantern Whoopie Pies | The Squeaky Mixer

Tips For Cream Cheese Frosting

Cream Cheese Frosting pairs so perfectly with Pumpkin and is super easy to make. The most important thing to remember when making cream cheese frosting is to ensure that the cream cheese and butter are room temperature when you begin to mix them together. Before the confectioner’s sugar and other ingredients are added to the cream cheese and butter mixture, there should be no lumps. Make sure to scrape down the sides of the bowl as you mix to ensure that everything is being mixed evenly and incorporated perfectly.

Jack-O-Lantern Whoopie Pies | The Squeaky Mixer

Jack-O-Lantern Pumpkin Whoopie Pies

Recipe by Maddison Koutrouba – thesqueakymixer.com
5.0 from 4 votes


Cooking time


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  • 3 cups all-purpose flour

  • 1/4 tsp. cloves

  • 1 Tbsp. ground cinnamon

  • 1/2 Tbsp. ground ginger

  • 1 tsp. baking soda

  • 1 tsp. baking powder

  • 1/2 tsp. salt

  • 2 cups light brown sugar, packed

  • 1 cup vegetable oil

  • 1 3/4 cups pumpkin puree

  • 2 eggs, room temperature

  • 2 tsp. vanilla extract

  • Cream Cheese Frosting Filling
  • 8 ounce block cream cheese, room temperature

  • 1/2 cup unsalted butter, room temperature

  • 3 1/4 cups confectioner’s sugar

  • 1/4 tsp. salt

  • 2 tsp. vanilla extract


  • Preheat the oven to 350 degrees F and line two cookie sheets with parchment paper. Set aside.
  • In a medium sized bowl, whisk together the dry ingredients. This should be the flour, loves, cinnamon, ginger, baking soda, baking powder, and salt. Set aside.
  • In a separate large bowl using a whisk or in the bowl of a stand mixer fit with the paddle attachment, mix together the brown sugar and oil until smooth. Add in the pumpkin puree, continue to mix.
  • Add the eggs one at a time mixing between each addition. Add in the vanilla. Continue to stir until the mixture is nice and smooth.
  • Add the dry ingredients to the wet and whisk until the batter is nice and smooth and all of the ingredients have been evenly incorporated. Scrape down the sides of the bowl using a silicone spatula to ensure that everything has combined evenly.
  • Scoop the batter in about 2 1/2 Tbsp. sized drops onto the prepared cookie sheets about 2″ apart to prevent them from touching in the oven. Bake for 10-12 minutes or until the sides have turned just a light golden brown and the top of the whoopie pie springs back when poked on top.
  • Allow the whoopie pies to cool completely on a wire rack before filling/ decorating. In the meantime you can prepare the cream cheese filling.
  • Begin my beating the cream cheese and butter together. You can do this step with an electric mixer or a stand mixer fit with the whisk attachment.
  • Once the butter and cream cheese is nice and smooth and there are no lumps, scrape down the sides of the bowl then add in the confectioner’s sugar, salt, and vanilla. Continue to mix until nice and smooth.
  • Once the whoopie pies have cooled, scoop a heaping 1 1/2 – 2 Tbsp. of filling in between each.
  • To decorate the whoopie pies, melt the chocolate in 30 second intervals mixing between each interval until the chocolate is completely melted and smooth. Transfer the melted chocolate in a piping bag.
  • Take your time piping on Jack-O-Lantern faces on top of each whoopie pie.
  • Enjoy!

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