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Milk Chocolate Stuffed Jack-O’-Lantern Cookies

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These milk chocolate stuffed jack-o’-lantern cookies are festive, buttery spiced cookies with gooey chocolate centers. Perfect for Halloween, they’re fun to decorate, kid-friendly, and a cozy autumn treat.

  • Total Time: 45 minutes
  • Yield: 30 cookies

Ingredients

1 1/2 cups (3 sticks) salted butter, softened

1 1/4 cups light brown sugar, packed

1 tbsp pure vanilla extract

2 large eggs, at room temperature

4 1/2 cups all-purpose flour

1 tsp baking soda

1 tsp cinnamon

1/2 tsp ginger

1/4 tsp nutmeg

1/2 tsp salt

12 oz milk chocolate, melted

2 tbsp salted butter (for coating)

3 tbsp cinnamon sugar (for coating)

Instructions

  1. In a large bowl, cream together butter, brown sugar, and vanilla until light and fluffy (3–5 minutes). Add eggs one at a time and mix until smooth.
  2. Mix in flour, baking soda, cinnamon, ginger, nutmeg, and salt until a dough forms.
  3. Lightly flour a work surface. Divide dough in half, flatten each into a disk, and roll out to 1/4 inch thickness. Cut pumpkin shapes with a cookie cutter and place on a parchment-lined baking sheet.
  4. Cut jack-o’-lantern faces into half the cookies. Freeze cookies for 15–20 minutes until firm. Re-roll scraps and repeat.
  5. Preheat oven to 350°F (175°C). Bake cookies for 8–12 minutes until lightly golden. Cool 5 minutes on baking sheet, then transfer to a wire rack.
  6. Melt 2 tbsp butter until lightly browned and nutty. Brush over top (face) cookies and sprinkle with cinnamon sugar.
  7. Spread melted chocolate over base cookies (without faces). Gently press top cookies onto them to sandwich together.
  8. Serve immediately or let chocolate firm before storing.

Notes

  • Use dark chocolate, white chocolate, or hazelnut spread for different fillings.
  • Add orange food coloring to the dough for extra festive cookies.
  • Substitute pumpkin pie spice for the cinnamon, ginger, and nutmeg blend.
  • Make gluten-free using a 1:1 baking flour blend.
  • Use smaller cookie cutters for bite-sized versions.
  • Author: Monica
  • Prep Time: 30 minutes
  • Cook Time: 15 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Nutrition

  • Serving Size: 1 cookie
  • Calories: 220
  • Sugar: 14g
  • Sodium: 120mg
  • Fat: 12g
  • Saturated Fat: 7g
  • Unsaturated Fat: 4g
  • Trans Fat: 0g
  • Carbohydrates: 26g
  • Fiber: 1g
  • Protein: 3g
  • Cholesterol: 30mg