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milk chocolate stuffed Jack O Lantern cookies - featured image

Milk Chocolate Stuffed Jack O Lantern Cookies


  • Author: Lauren Diaz
  • Total Time: 1 hour 20 minutes
  • Yield: 18-20 cookies 1x

Description

Festive Halloween sugar cookies stuffed with creamy milk chocolate and decorated with playful pumpkin faces. These cookies are easy to make, fun to decorate, and perfect for parties or cozy fall baking.


Ingredients

Scale
  • 2 1/2 cups all-purpose flour (plus extra for rolling)
  • 1/2 tsp baking powder
  • 1/4 tsp salt
  • 3/4 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg, room temperature
  • 1 1/2 tsp pure vanilla extract
  • Orange gel food coloring
  • 5 oz milk chocolate bars or chocolate chips
  • Black writing gel or melted chocolate (for faces)
  • Green writing gel or green icing (for stems)
  • Optional: colored sprinkles or sanding sugar

Instructions

  1. In a large bowl, whisk together flour, baking powder, and salt. Set aside.
  2. Cream butter and sugar with an electric mixer until pale and fluffy (2-3 minutes).
  3. Beat in egg and vanilla until just combined.
  4. Mix in orange gel food coloring until dough is a bright pumpkin shade.
  5. Slowly add flour mixture to wet ingredients, mixing just until a soft dough forms. Add 1-2 tbsp more flour if sticky.
  6. Wrap dough in plastic and chill for 30-45 minutes.
  7. Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
  8. Roll out dough on a floured surface to 1/4-inch thickness. Cut out pumpkin shapes in pairs (tops and bottoms).
  9. Use a small knife or toothpick to carve out faces on half the cookies (tops).
  10. Place about 1/2 tbsp milk chocolate or a few chips in the center of each bottom cookie. Gently press a face cookie on top and seal edges.
  11. Bake 10-12 minutes, until edges are set and bottoms are lightly golden.
  12. Transfer cookies to a rack to cool.
  13. Once cool, decorate faces with black gel or melted chocolate and add green stems with icing. Sprinkle with sanding sugar if desired.
  14. Let decorations set for 10 minutes before serving.

Notes

Chill dough for best shape and texture. Use parchment paper for easy cleanup. Faces don’t need to be perfect—personality is key! For gluten-free or vegan options, substitute flour, butter, and egg as needed. Store cookies in an airtight container for up to 4 days or freeze for 2 months.

  • Prep Time: 25 minutes
  • Cook Time: 12 minutes
  • Category: Dessert
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie
  • Calories: 180
  • Sugar: 13
  • Sodium: 60
  • Fat: 8
  • Saturated Fat: 5
  • Carbohydrates: 24
  • Fiber: 1
  • Protein: 2

Keywords: Halloween cookies, stuffed cookies, milk chocolate, pumpkin cookies, festive dessert, kid-friendly, party treats, sugar cookies, fall baking