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Holiday Cookies Pumpkin Shortbread
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Pumpkin Shaped Chocolate Stuffed Shortbread Cookies

Buttery shortbread cookie sandwiches stuffed with creamy chocolate filling make these Pumpkin Shortbread Cookies perfect for Halloween.
Course Dessert
Cuisine American
Keyword chocolate, pumpkin, shortbread
Prep Time 45 minutes
Cook Time 12 minutes
Chill 15 minutes
Servings 12 cookies

Ingredients

Cookies

  • 1 cup butter softened (2 sticks)
  • ½ cup confectioner's sugar
  • 1 tsp vanilla extract
  • ½ tsp salt
  • 2 cups all-purpose flour
  • 3 tbsp milk

Chocolate Filling

  • ¼ cup Nutella
  • ¼ cup confectioner's sugar
  • ¼ cup heavy cream
  • ½ tsp flake sea salt or ¼ tsp kosher salt

To Decorate

  • Black, Orange, and Green Food Coloring
  • Water

Instructions

Make the Cookies

  • In the bowl of a stand mixer fitted with the paddle attachment, whip the butter on high speed for 2-3 minutes, or until it is light and fluffy.
  • Add the confectioners sugar, vanilla, and salt. Mix again on low speed just until the sugar is fully combined— about 1 minute.
  • Next, alternate between adding the flour and milk while the mixer is on low speed. First, add half the flour, then half the milk, then the remaining flour, then the remaining milk.
  • Continue mixing on low speed just until the dough forms a ball around the paddle.
  • Form the dough into a disk and wrap it in plastic wrap. Refrigerate for 15 minutes.
  • In the meantime, preheat your oven to 350F. Line two large baking sheets with parchment paper.
  • Lightly sprinkle your work surface with flour and roll the dough out until it is 1/4” thick.
  • Use a pumpkin cookie cutter to cut the dough and transfer the cookies to the prepared baking sheet.
  • Note: I used a cookie cutter that was 2” in diameter. Additionally, make sure to place the cookies at least 1” apart on the baking sheet.
  • Bake the cookies for 10-12 minutes, or until the edges are just starting to turn golden brown. Set them aside to cool completely.

Make the Chocolate Filling

  • Combine the Nutella, confectioner's sugar, cream, and salt in the bowl of a stand mixer fitted with the paddle attachment.
  • Beat on medium-high speed until it is fluffy and no large lumps of powdered sugar remain— about 2 minutes.

Assemble and Decorate

  • Once the cookies have cooled completely, spread one cookie with 1-2 tsp of chocolate filling (depending on the size) and top it with a second cookie. Press down gently to make sure the filling spreads all the way to the edge. Note: Be gentle! These are soft cookies.
  • To decorate, combine 1/4 tsp of gel food coloring with a few drops of water and stir it until the food coloring is fully dissolved.
  • Use a food-safe paintbrush to paint the jack o lantern face, if desired. Allow the paint to dry for at least 20 minutes before touching.
  • Note: It is easiest to paint the whole cookie orange before adding the black eyes and mouth.
  • Store the cookies in an airtight container for up to 3 days.

Notes

This dough is very soft— feel free to use as much flour as needed to prevent it from sticking to your work surface.
I used this cookie press (link in post) to make the Jack O Lantern face easier to paint.