Pumpkin Spice Jack-O-Lantern Cookies | The Squeaky Mixer

Pumpkin Spice Jack-O-Lantern Cookies

I cannot get enough of these Pumpkin Spice Jack-O-Lantern Cookies. These cookies are packed with pumpkin flavor and sandwiches between two soft, melt-in-your-mouth vanilla sugar cookies. The sugar cookies are not overly sweet, which balances perfectly with the pumpkin spice buttercream and of course the pumpkin pie filling that adds the perfect punch of pumpkin. These cookies are perfect for the season.

Pumpkin Spice Jack-O-Lantern Cookies Dough Rolled Out | The Squeaky Mixer

Key Ingredients

  • Butter – Creaming the butter and confectioner’s sugar is the first step in making the sugar cookies. This step, while it may not seem like it does much, is one of the most important steps in this recipe. It is the base for our sugar cookies and will impact the end results overall shape and texture of each cookie. Having room temperature butter will give you the best results – cold butter will not combine as easy. Creaming the butter and confectioner’s sugar creates tiny air pockets throughout the mixture which will give the cookie a light, tender texture.
  • Egg – Use room temperature eggs – I promise it makes a difference. It takes about 20 minutes for an egg to come to room temperature, otherwise you can place it in lukewarm water fro about 5-10 minutes to speed up the process. Room temperature ingredients combine together so much easier and will give you a better textured end result. The egg in our sugar cookies not only help bind our ingredients together, but the egg will also help to hydrate the ingredients to create a cohesive dough. This will lead to the soft, slightly crisp, chewy texture in our cookies.
  • Confectioner’s Sugar – We use confectioner’s sugar in both the sugar cookies and in the buttercream. Starting with the sugar cookies, the confectioner’s sugar seems to raise a lot of eyebrows and people tend to ask “why not granulated sugar?”. Confectioner’s sugar helps to make these cookies extremely tender and soft. These cookies almost lean towards the flavor and texture of shortbread than traditional sugar cookies. The confectioner’s sugar in the buttercream of course helps to make our buttercream smooth and voluminous. Otherwise it’d be a butter, vanilla cream…I’d rather have a regular buttercream with confectioner’s sugar.
  • Pumpkin Pie Spice – Pumpkin pie spice typically contains cinnamon, ginger, nutmeg, cloves, and allspice. These spices together not only smell incredible but they have all the warm toasty flavors of the season. Adding these spices to buttercream pairs so perfectly with these sugar cookies and adds the perfect amount of pumpkin kick in each bite.
  • Pumpkin Puree – The pumpkin pie filling is optional in this recipe, but really takes these cookies to the next level. With the different textures of the cookie, the buttercream and then this pumpkin pie filling made from pumpkin puree really just are matches made in heaven.
Pumpkin Spice Jack-O-Lantern Cookies | The Squeaky Mixer

Do I Need To Chill Cookie Dough?

This recipe really relies on our handy dandy freezers and fridges. Keeping the dough cold and firm will allow us to work with it easier and not lose the shape and integrity of the dough. After rolling out each color of dough, be sure to follow each step accordingly to ensure that our dough stays nice and cold.

Another bonus to chilling dough, and this goes for most cookie dough recipes, AND not to get too nerdy BUT chilling the dough solidifies the fats in butter, or whatever fat you’re using, in the dough. When the cookies bake, these solid fats take longer to melt, which which will help keep our shape of our cookies perfect and will give us a more tender texture.

Pumpkin Spice Jack-O-Lantern Cookies Dough | The Squeaky Mixer

Coloring Our Pumpkin Spice Jack-O-Lantern Cookie Dough

I wanted two different shades of orange for my pumpkins. You can make as many shades as you want or as little as you want. I will always recommend Americolor Food Gel. A little goes a long way and gives you the most vibrant, beautiful colors. Click here for the link.

Edible Markers

This step is optional, but adding Jack-O-Lantern faces to these cookies really takes them to the next level and is sure to “wow” a crowd. I use edible markers that I purchase from amazon. You can find them here. if you’re worried you’re not an artist, you can either skip this step and keep the cookies as they are, super cute festive fall pumpkins, OR you can google different pumpkin faces and practice on paper a few times before taking to the cookies.

More Pumpkin Recipes…

I thrive this time of year, give me pumpkin everything, colder weather, sweaters, and Christmas right around the corner. I hope you enjoy some more of my Pumpkin Recipes like my Pillsbury Pumpkin Cupcakes, the most delicious Pumpkin Banana Bread Muffins With A Cream Cheese Filling, these copycat Pillsbury Pumpkin Sugar Cookies, or Harry Potter Cupcakes.

Pillsbury Pumpkin Sugar Cookie Cupcakes | The Squeaky Mixer

Pillsbury Pumpkin Sugar Cookie Cupcakes

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There is no denying that the Pillsbury Pumpkin Sugar Cookies are the most cozy and nostalgic reminder that autumn is here or in this case, right around the corner. As…
Copycat Pillsbury Pumpkin Sugar Cookies | The Squeaky Mixer

Copycat Pillsbury Pumpkin Sugar Cookies

Posted on
Seeing Pillsbury Pumpkin Sugar Cookies in grocery stores for the first time every year is the warmest feeling I know. As a kid, my sisters and I would eat most…
Harry Potter Cupcakes | The Squeaky Mixer

Harry Potter Cupcakes

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Spooky season is right around the corner and for a lot of you this also means binge watching all the Harry Potter movies. Even though in my world, binging all…
Pumpkin Spice Jack-O-Lantern Cookies | The Squeaky Mixer

Pumpkin Spice Jack-O-Lantern Cookies

Recipe by Maddison Koutrouba – thesqueakymixer.com
5.0 from 1 vote


Cooking time


Total time




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  • 1 cup unsalted butter

  • 1 1/2 cup confectioners sugar

  • 1 egg

  • 2 tsp. vanilla extract

  • 2 3/4 cups all-purpose flour

  • 1/4 tsp. baking powder

  • 1/2 tsp. salt

  • Pumpkin Spice Buttercream
  • 3/4 cups unsalted butter, softened

  • 2 1/2 cups confectioner’s sugar

  • 3-4 Tbsp. heavy whipping cream

  • 1 1/2 tsp. pumpkin pie spice

  • 1/4 tsp. salt

  • 1/2 tsp. vanilla

  • Pumpkin Pie Filling
  • 1/2 cup pumpkin puree

  • 4 Tbsp. brown sugar

  • 1 tsp. vanilla


  • In the bowl of a stand mixer fit with the paddle attachment or with a hand held electric mixer, cream together the butter and sugar on low speed until smooth.
  • Scrape down the sides of the bowl as you go and add in the egg and vanilla. Continue to mix on low speed.
  • In a separate bowl, whisk together the flour, baking powder and salt.
  • Add the dry ingredients to the wet and mix until the dough comes together nicely. Scrape down the sides of the bowl as needed to get the dough evenly mixes throughout.
  • Remove 1/4 cup of dough and dye it a dark shade of orange. Remove another 1/4 cup of dough is dye it a lighter shade of orange. Lastly, remove about 1 tablespoon of dough and dye it brown.
  • Roll out the remaining uncolored dough to about 1/8β€³ thick on top of parchment paper for easy movement.
  • Roll out the dark orange, light orange, and brown dough separately to the same thickness as the uncolored dough.
  • Place each rolled out sheet of dough onto a cookie sheet then into the freezer to chill for about 15-20 minutes.
  • Preheat the oven to 400 degrees after the dough has chilled.
  • Remove the orange sheets of dough and cut out as many small and medium sized circles as you can.
  • Place the small circles all over the uncolored sheet of dough. Feel free to pinch the sides of the circles to help give them a more pumpkin-y shape. Cut the brown dough into little rectangles then place them at the top of each pumpkin. Place parchment over this, then use a rolling pin to flatten the pumpkins into the uncolored dough.
  • Use a larger pumpkin cutter to cut out as many cookies as you can. Place these onto a cookie sheet fit with parchment paper 1 1/2″ apart then bake for 7-8 minutes. Re-roll the scraps and use these cookies as the bottom side of the sandwich cookie since it will not be seen.
  • Let the cookies cool completely on a cooling rack before assembling.
  • To make the pumpkin spice buttercream filling, cream together the butter and confectioner’s sugar. Slowly add in the vanilla and 1 tablespoon of cream at a time until the buttercream reaches a smooth consistency. Add in the pumpkin pie spice and salt. Set this aside.
  • To make the pumpkin pie filling, mix all of the ingredients together (pumpkin puree, brown sugar, and vanilla together until well combined. Set aside.
  • Once the cookies are cooled, pipe a circle on the perimeter on the bottom side of a cookie, then fill the circle of buttercream with the pumpkin pie filling. Repeat this step for each sandwich cookie
  • This step is optional, but you can use an edible marker to draw Jack-O-Lantern faces on each pumpkin! Get creative and have fun with this step.
  • Enjoy! πŸŽƒ

Did you make this recipe?

Tag @thesqueakymixer on Instagram! I love to see what you all create.

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