Milk Chocolate Stuffed Jack-O’-Lantern Cookies – Spooky & Fun Halloween Treats

Nothing says Halloween like cookies that surprise you from the inside! These Jack-O’-Lantern cookies are soft, pumpkin-flavored, and filled with rich milk chocolate, making every bite a festive delight.

Perfect for Halloween parties, school treats, or simply indulging in seasonal flavors, these cookies are fun to make and even more fun to eat. The pumpkin spice adds warmth, while the melted chocolate gives a gooey center that everyone loves.


Why You’ll Love This Recipe

  • Festive & fun: Perfect for Halloween parties and trick-or-treating.
  • Soft & chewy: Pumpkin puree keeps cookies moist.
  • Chocolate surprise: Each cookie hides a gooey milk chocolate center.
  • Easy to decorate: Simple jack-o’-lantern faces with minimal icing or chocolate.
  • Kid-friendly: Baking and decorating is a fun activity for kids and adults alike.

Ingredients

Cookie Dough:

  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1/2 cup brown sugar, packed
  • 1 large egg
  • 1 tsp vanilla extract
  • 1/2 cup pumpkin puree (unsweetened)
  • 2 1/2 cups all-purpose flour
  • 1 tsp baking soda
  • 1/2 tsp salt
  • 1 tsp pumpkin spice

Chocolate Filling & Decoration:

  • 12 milk chocolate squares or chocolate chips (for stuffing)
  • Black or dark chocolate icing or melted chocolate for faces
  • Optional: orange icing for extra decoration

Instructions

  1. Preheat oven & prep pans:
    Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
  2. Cream butter & sugars:
    In a large bowl, cream softened butter, granulated sugar, and brown sugar until light and fluffy.
  3. Add egg, vanilla & pumpkin:
    Beat in the egg, vanilla extract, and pumpkin puree until well combined.
  4. Mix dry ingredients:
    In a separate bowl, whisk together flour, baking soda, salt, and pumpkin spice. Gradually mix into wet ingredients to form soft dough.
  5. Form cookies & add chocolate:
    Scoop about 2 tablespoons of dough, flatten slightly, and place a milk chocolate square in the center. Wrap dough around the chocolate to fully enclose it.
  6. Shape & bake:
    Roll dough into balls, place on baking sheet about 2 inches apart, and slightly flatten. Bake 12–14 minutes until edges are set but centers are soft.
  7. Cool & decorate:
    Let cookies cool 5–10 minutes. Use melted chocolate or icing to draw jack-o’-lantern faces on each cookie.
  8. Serve & enjoy:
    Best served warm for gooey chocolate centers, or store in an airtight container for up to 3 days.

Pro Tips

  • Chocolate placement: Ensure chocolate is fully covered by dough to prevent leaking.
  • Pumpkin puree: Use unsweetened pumpkin puree for balance; canned pumpkin pie filling is too sweet.
  • Decorating: Piping chocolate with a small tip or zip-top bag makes detailed faces easier.
  • Storage: Keep in airtight container at room temperature; reheat slightly for molten chocolate.

Fun Variations

  1. White chocolate filling: Substitute milk chocolate with white chocolate for contrast.
  2. Mini cookies: Perfect for party platters or kids’ snacks.
  3. Spicy pumpkin: Add a pinch of cayenne or ginger for a warming kick.
  4. Double chocolate pumpkin: Mix cocoa powder into dough for chocolate pumpkin cookies.
  5. Vegan option: Use plant-based butter and chocolate to make vegan-friendly.
  6. Gluten-free: Substitute 1:1 gluten-free flour blend.
  7. Festive icing: Use colored icing to make more detailed faces or patterns.

Storage & Reheating

  • Room temperature: 3–4 days in airtight container.
  • Freeze: Dough can be frozen before baking for up to 1 month. Bake from frozen, adding 2–3 minutes to baking time.
  • Reheat: Warm slightly in oven or microwave for gooey chocolate center.

Nutrition Information (Per Cookie, approx.)

  • Calories: 180
  • Protein: 2g
  • Fat: 9g
  • Carbohydrates: 22g
  • Fiber: 1g
  • Sugar: 12g
  • Sodium: 100mg

Halloween Jack-O’-Lantern Cookies

Soft pumpkin cookies stuffed with milk chocolate and decorated with spooky jack-o’-lantern faces. Perfect for Halloween treats and parties.
Prep Time 15 minutes
Cook Time 12 minutes
Total Time 27 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American, Halloween
Calories: 180

Ingredients
  

Cookie Dough
  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 0.5 cup brown sugar packed
  • 1 egg large
  • 1 tsp vanilla extract
  • 0.5 cup pumpkin puree unsweetened
  • 2.5 cups all-purpose flour
  • 1 tsp baking soda
  • 0.5 tsp salt
  • 1 tsp pumpkin spice
Filling & Decoration
  • 12 milk chocolate squares or chips for stuffing
  • black or dark chocolate icing for faces
  • orange icing optional decoration

Equipment

  • Mixing bowls
  • Baking sheet
  • Parchment paper
  • Hand mixer or stand mixer

Method
 

  1. Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
  2. Cream butter, granulated sugar, and brown sugar until light and fluffy.
  3. Beat in egg, vanilla extract, and pumpkin puree.
  4. Mix dry ingredients separately, then combine with wet ingredients to form dough.
  5. Scoop 2 tablespoons dough, place chocolate in center, wrap dough to enclose chocolate.
  6. Roll dough into balls, flatten slightly, bake 12–14 minutes.
  7. Cool 5–10 minutes. Decorate with jack-o’-lantern faces using chocolate or icing.
  8. Serve warm or store in airtight container.

Notes

Use unsweetened pumpkin puree for balance. Add more chocolate for extra gooeyness.

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