Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe

Celebrate Halloween in the most delicious way with this Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe. Perfectly soft pumpkin-shaped cookies hide a creamy milk chocolate center that melts in your mouth. Fun, festive, and irresistible, this recipe guarantees smiles around the table, whether for trick-or-treaters, parties, or family baking nights. The warm pumpkin flavor paired with rich milk chocolate makes every bite a little Halloween magic.

Why You’ll Love This Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe

  • Irresistible flavor combo: Sweet pumpkin meets creamy milk chocolate for an unforgettable taste.

  • Family-friendly activity: Fun to shape, decorate, and share with kids.

  • No professional skills needed: Simple step-by-step instructions make baking stress-free.

  • Perfect for Halloween parties: Eye-catching cookies shaped like Jack-O’-Lanterns will impress guests.

  • Customizable sweetness: Adjust sugar or chocolate type for dietary needs.

  • Budget-friendly ingredients: Uses pantry staples without breaking the bank.

  • Make-ahead friendly: Bake in advance and store for days without losing flavor.

  • Sensory delight: Soft, pillowy texture with a gooey chocolate surprise in the center.

Ingredients

Cookies:

  • 1 ¾ cups all-purpose flour (or gluten-free blend)

  • ½ teaspoon baking soda

  • ½ teaspoon baking powder

  • ¼ teaspoon salt

  • 1 teaspoon pumpkin spice (optional, enhances seasonal flavor)

  • ½ cup unsalted butter, softened

  • ½ cup granulated sugar

  • ½ cup brown sugar, packed

  • 1 large egg

  • 1 teaspoon vanilla extract

  • ½ cup pumpkin puree (fresh or canned)

Chocolate Filling:

  • 6 ounces milk chocolate, chopped or chocolate chips

  • 1 tablespoon heavy cream (optional for creamier filling)

Decorations (optional):

  • Orange and green royal icing for Jack-O’-Lantern faces

  • Sprinkles or edible glitter

Tips & Substitutions:

  • Swap milk chocolate with dark or white chocolate for variation.

  • Use coconut oil instead of butter for dairy-free cookies.

  • Pumpkin puree adds moisture; canned pumpkin works best if fresh is unavailable.

  • Ensure all ingredients are at room temperature for smooth mixing.

Instructions

1. Preheat & Prep

Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat. Lightly grease if necessary to prevent sticking.

2. Mix Dry Ingredients

In a large bowl, whisk together flour, baking soda, baking powder, salt, and pumpkin spice. Set aside.

3. Cream Butter & Sugar

In a separate bowl, beat the softened butter with both sugars until light and fluffy (about 3–4 minutes). Add egg, vanilla extract, and pumpkin puree. Mix until smooth.

4. Combine Wet & Dry Ingredients

Gradually fold the dry ingredients into the wet mixture. Avoid overmixing; the dough should be soft but manageable.

5. Prepare Chocolate Filling

In a small bowl, combine milk chocolate and heavy cream (optional). Melt gently in the microwave or double boiler until smooth. Set aside to cool slightly.

6. Shape Cookies

  • Scoop a tablespoon of dough, flatten it slightly, and place a small spoonful of melted milk chocolate in the center.

  • Cover with another tablespoon of dough and seal the edges completely.

  • Shape into a round, slightly flattened pumpkin form. For authentic Jack-O’-Lantern look, gently press the top and use a toothpick to create grooves.

7. Bake

Place cookies on the prepared baking sheet, spacing them 2 inches apart. Bake for 12–15 minutes until edges are lightly golden. Centers should remain soft.

8. Cool & Decorate

Allow cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack. Decorate with royal icing to create Jack-O’-Lantern faces.

Pro Tips for Perfect Milk Chocolate Stuffed Jack-O’-Lantern Cookies

How do I prevent the chocolate from leaking?

Seal the dough around the chocolate completely and slightly chill the filled cookies before baking. This ensures the chocolate stays centered.

Can I make these cookies ahead of time?

Yes! Store baked cookies in an airtight container for up to 5 days. Dough can be refrigerated for up to 3 days before baking.

Can I use chocolate chips instead of a solid filling?

Absolutely. A few chocolate chips in the center create a soft, gooey chocolate core, perfect for kids.

Why is my cookie dough sticky?

Add a tablespoon of flour at a time until dough is manageable. Avoid overmixing, which can make cookies tough.

Best Ways to Serve

  • Serve fresh with a warm cup of cocoa or spiced tea.

  • Perfect for Halloween party platters, paired with pumpkin-shaped candies.

  • Wrap individually as trick-or-treat gifts.

Nutrition (per cookie)

  • Calories: 180

  • Fat: 9g

  • Saturated Fat: 5g

  • Carbohydrates: 22g

  • Fiber: 1g

  • Sugar: 13g

  • Protein: 2g

  • Sodium: 80mg

Percent Daily Values are based on a 2,000-calorie diet.

Storage & Leftovers

  • Room Temperature: Keep in an airtight container for up to 5 days.

  • Freezer: Wrap individually and freeze for up to 2 months. Thaw at room temperature before serving.

  • Reheating: Warm slightly in a microwave (10–15 seconds) for that melty chocolate center.

FAQ

Can I make these cookies gluten-free?
Yes, use a 1:1 gluten-free flour blend. Add 1 tsp xanthan gum if your mix doesn’t already contain it.

Can I substitute pumpkin with sweet potato?
Sweet potato puree works beautifully, though it may slightly alter sweetness and texture.

Are these cookies suitable for kids?
Definitely! They’re soft, chocolaty, and fun to decorate for all ages.

How do I store chocolate-stuffed cookies without melting?
Cool completely and keep in a cool room. Avoid storing in direct sunlight or near warm appliances.

Variations

  • Dietary: Vegan milk chocolate and coconut oil for a plant-based version.

  • Flavor: Add cinnamon chips or nutmeg for a spiced twist.

  • Regional: Swap milk chocolate for Mexican chocolate with cinnamon for a festive regional flavor.

  • Mini Version: Make bite-sized cookies for party platters or lunchboxes.

Conclusion

Bring Halloween magic to life with this Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe. The combination of soft pumpkin cookies with a gooey milk chocolate center creates a treat that’s as fun to make as it is to eat. Share your creations on social media, tag friends, and join the festive baking fun. Unlock this recipe’s full flavor and make your Halloween unforgettable!

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