Tray of Jack Skellington–inspired Halloween cookies shaped like pumpkins, ghosts, and skeleton faces, decorated with festive icing

Halloween is the perfect time to get creative in the kitchen, and these Jack Skellington–inspired cookies will steal the show at any spooky party. They’re buttery, melt-in-your-mouth sandwich cookies filled with chocolate and decorated to look like Jack’s mischievous grin.


🛒 Ingredients

For the Cookies (Shortbread Base):

  • 1 cup (2 sticks) unsalted butter, softened
  • 1 cup powdered sugar
  • 1 teaspoon vanilla extract
  • 2 cups all-purpose flour
  • Pinch of salt

For the Filling:

  • 4 oz dark chocolate (melted)
  • 2 tablespoons heavy cream

For Decorating:

  • Black food coloring gel or edible marker
  • Royal icing (optional for details)

🥣 Instructions

  1. Make the Dough:
    • Cream butter and sugar together until fluffy.
    • Add vanilla extract, then slowly mix in flour and salt until dough forms.
    • Chill dough in the fridge for 30 minutes.
  2. Shape the Cookies:
    • Roll out dough to ¼ inch thick.
    • Use a round cookie cutter to cut out circles (Jack’s face).
    • Place on parchment-lined baking sheet.
  3. Bake:
    • Bake at 350°F (175°C) for 10–12 minutes until edges are lightly golden.
    • Cool completely before decorating.
  4. Prepare the Filling:
    • Melt chocolate with cream until smooth.
    • Spread onto the bottom of one cookie, then sandwich with another.
  5. Decorate Jack’s Face:
    • Using edible black marker or gel icing, draw Jack’s signature stitched smile, nose, and hollow eyes.
    • For a bolder look, pipe details with black royal icing.

🎃 Tips & Variations

  • Add pumpkin spice to the dough for a seasonal twist.
  • Use white chocolate filling for contrast.
  • Package in treat bags for Halloween gifts.