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Milk Chocolate Stuffed Jack O Lantern Cookies
Sarah namedy

Milk Chocolate Stuffed Jack-O-Lantern Cookies

These festive jack-o-lantern cookies feature buttery spiced shortbread filled with creamy milk chocolate — a Halloween treat that’s equal parts fun, spooky, and deliciously indulgent.
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Prep Time 30 minutes
Cook Time 12 minutes
Total Time 42 minutes
Servings: 20 cookies
Course: Dessert
Cuisine: American
Calories: 240
Ingredients Equipment Method Notes

Ingredients
  

  • 1 1/2 cups salted butter, softened (3 sticks)
  • 1 1/4 cups light brown sugar, packed
  • 1 tablespoon pure vanilla extract
  • 2 large eggs, at room temperature
  • 4 1/2 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1 teaspoon ground cinnamon
  • 1/2 teaspoon ground ginger
  • 1/4 teaspoon ground nutmeg
  • 1/2 teaspoon salt
  • 12 oz milk chocolate, melted
  • 2 tablespoons butter (for brushing topping)
  • 2 tablespoons cinnamon sugar (for topping)

Equipment

  • Mixing bowls
  • Hand or stand mixer
  • Rolling pin
  • pumpkin-shaped cookie cutter
  • paring knife
  • Baking sheet
  • Parchment paper
  • Wire cooling rack
  • Small saucepan

Method
 

  1. In a large mixing bowl, cream together softened butter and brown sugar until light and fluffy, about 3–5 minutes. Mix in vanilla extract, then beat in the eggs one at a time until well incorporated.
  2. Gradually add flour, baking soda, cinnamon, ginger, nutmeg, and salt to the wet mixture. Stir until the dough forms a cohesive ball. Add a little more flour if the dough is too sticky.
  3. Flour your work surface and divide dough into two halves. Roll each to 1/4-inch thickness. Cut with pumpkin-shaped cookie cutters. For half of the cookies, cut out jack-o-lantern faces using a knife or smaller cutter. Chill cutouts in the freezer for 15–20 minutes.
  4. Preheat oven to 350°F (175°C). Bake chilled cookies for 8–12 minutes or until lightly golden at the edges. Cool on the sheet for 5 minutes, then transfer to a wire rack.
  5. Melt 2 tablespoons of butter until lightly golden and fragrant. Brush over the top of jack-o-lantern face cookies, then sprinkle with cinnamon sugar.
  6. Spread melted milk chocolate on the flat sides of the base cookies. Gently place the decorated jack-o-lantern cookies on top to form sandwich cookies. Allow chocolate to set before serving.

Notes

To get crisp, well-defined pumpkin shapes, chill the dough before baking. You can substitute dark or white chocolate for the filling. Store in an airtight container for up to 5 days or freeze for later.