How to Make Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Delight in festive fun with Milk Chocolate Stuffed Jack-O’-Lantern Cookies—the perfect Halloween treat that combines soft, spiced pumpkin cookies with a gooey milk chocolate surprise inside. These charming, spooky cookies are not only visually captivating but also bursting with comforting autumnal flavors, making them an irresistible addition to your seasonal festivities or any sweet occasion.

Why You’ll Love This Recipe

• Delightful surprise inside: Each cookie hides a melty milk chocolate center that perfectly complements the pumpkin spice flavor.
• Festive and fun: The Jack-O’-Lantern design adds a playful, seasonal charm that’s ideal for Halloween parties or family treats.
• Simple and approachable: This recipe uses straightforward ingredients and easy techniques, accessible for bakers of all levels.
• Perfect texture: Soft, chewy cookies with just the right amount of spice enhance the autumn vibe.
• Great for sharing: Makes an impressive batch that is ideal for gifting or handing out to trick-or-treaters.

Ingredients You’ll Need

Each ingredient in this Milk Chocolate Stuffed Jack-O’-Lantern Cookies recipe is chosen to build the perfect balance of flavor, texture, and seasonal appeal. From the warm spices to the rich milk chocolate, every component plays an essential role.

• All-purpose flour: Provides structure to the soft pumpkin cookie dough.
• Baking soda and baking powder: These leavening agents help achieve a light, chewy texture.
• Ground cinnamon and pumpkin pie spice: Infuse the cookies with classic autumn warmth and spice.
• Salt: Balances sweetness and enhances flavor complexity.
• Unsalted butter: Adds richness and a tender crumb.
• Granulated sugar and brown sugar: Brown sugar contributes moisture and a subtle caramel note while granulated sugar ensures crisp edges.
• Egg: Binds the ingredients and adds moisture.
• Pumpkin puree: Delivers moisture and a mild earthy sweetness with a vibrant orange color.
• Vanilla extract: Enhances the overall aroma and flavor depth.
• Milk chocolate squares or chunks: The gooey center that makes these cookies special and irresistible.

Variations for Milk Chocolate Stuffed Jack-O’-Lantern Cookies

One of the best things about this recipe is how easy it is to tailor it to your taste preferences or dietary needs. Feel free to get creative and experiment with these tasty variations.

• Dark chocolate filling: Swap milk chocolate with dark chocolate for a deeper, richer center.
• White chocolate twist: Use white chocolate chunks for a sweeter, creamier inside surprise.
• Vegan adaptation: Replace butter with coconut oil and use flax eggs instead of regular eggs to make it plant-based.
• Nutty upgrade: Add chopped pecans or walnuts to the dough for a crunchy texture.
• Spice it up: Increase the pumpkin pie spice or add a pinch of nutmeg for more pronounced holiday flavors.

How to Make Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Step 1: Prepare the Dough

In a medium bowl, whisk together all-purpose flour, baking soda, baking powder, cinnamon, pumpkin pie spice, and salt. In a separate large bowl, beat the softened butter with granulated and brown sugars until creamy and fluffy. Add the egg, pumpkin puree, and vanilla extract, mixing until fully combined. Gradually incorporate the dry ingredients into the wet mixture, forming a soft dough that’s slightly sticky but manageable.

Step 2: Shape the Cookies

Roll out the dough on a lightly floured surface to about 1/4 inch thickness. Use a Jack-O’-Lantern-shaped cookie cutter to cut out as many shapes as possible. Then, cut out an equal number of solid cookie shapes without faces to act as lids. Alternatively, prepare rounds if you don’t have a themed cutter.

Step 3: Stuff with Milk Chocolate

Place a small piece of milk chocolate in the center of each Jack-O’-Lantern cutout. Gently press the solid cookie “lid” on top, sealing the edges by lightly pinching or using a fork to create a decorative border that locks in the filling.

Step 4: Carve the Faces

Carefully cut out the Jack-O’-Lantern features (eyes, nose, mouth) on the top cookie layer using a small paring knife or cookie-carving tool. This makes the milk chocolate filling peek through during baking, adding to the eerie effect.

Step 5: Bake the Cookies

Preheat your oven to 350°F (175°C). Place the stuffed cookies on a parchment-lined baking sheet and bake for 10-12 minutes or until the edges are lightly golden. Baking will soften the cookie and melt the milk chocolate inside.

Step 6: Cool and Enjoy

Allow the cookies to cool on the pan for 5 minutes before transferring to a wire rack. The chocolate center will thicken as they cool, creating an indulgent surprise with every bite.

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

• Chill the dough: Refrigerate the dough for 30 minutes before rolling to prevent sticky handling and maintain shape.
• Seal edges well: Press cookie layers firmly together to avoid chocolate leaking during baking.
• Use quality chocolate: Opt for good-quality milk chocolate to ensure a smooth, creamy filling.
• Don’t overbake: Remove cookies once edges turn golden to keep them soft and chewy.
• Cut shapes carefully: Use a sharp knife or fine cookie cutters to create detailed Jack-O’-Lantern faces.

How to Serve Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Garnishes

Sprinkle a light dusting of powdered sugar or cinnamon over the cooled cookies to add a festive touch. Fresh orange zest can also enhance the pumpkin flavor and bring a burst of color.

Side Dishes

Pair these cookies with a warm cup of spiced cider, hot chocolate, or a creamy pumpkin latte for a perfectly cozy treat. They also complement ice cream or whipped cream for a decadent dessert platter.

Creative Ways to Present

Arrange the cookies on a rustic wooden tray surrounded by mini pumpkins, autumn leaves, and fairy lights to set a Halloween-themed vibe. Wrapping individual cookies in clear cellophane with orange ribbons makes delightful party favors or gifts.

Make Ahead and Storage

Storing Leftovers

Store leftover Milk Chocolate Stuffed Jack-O’-Lantern Cookies in an airtight container at room temperature for up to 3 days to maintain softness and freshness.

Freezing

Freeze unbaked cookie dough wrapped tightly in plastic wrap for up to 3 months. Alternatively, freeze baked cookies in a sealed container with parchment layers to prevent sticking for up to 2 months.

Reheating

Gently warm the cookies in a microwave for 10-15 seconds or in a low-temperature oven to re-melt the chocolate center and bring out that gooey goodness.

FAQs

Can I use dark or white chocolate instead of milk chocolate?

Absolutely! Dark or white chocolate chunks work beautifully as filling alternatives, letting you customize the flavor and sweetness to your liking.

How do I prevent the chocolate from leaking during baking?

Make sure to seal the cookie edges very well around the chocolate and avoid overfilling to keep the melted chocolate contained inside.

Can I make these cookies gluten-free?

Yes, swap the all-purpose flour with a gluten-free baking blend, and your cookies will still turn out delicious and festive.

What’s the best way to carve Jack-O’-Lantern faces?

Use a small, sharp paring knife or a precision cookie cutter to safely and neatly cut out the facial features without damaging the cookie edges.

How long do these cookies stay fresh?

Stored properly in an airtight container, these cookies stay soft and tasty for about 3-4 days at room temperature.

Final Thoughts

There is something truly magical about sinking your teeth into Milk Chocolate Stuffed Jack-O’-Lantern Cookies, where the warm spices and gooey center bring both comfort and delight. Whether you’re baking for a Halloween party, a cozy family night, or just because you love pumpkin and chocolate, this recipe is sure to become a seasonal favorite. Don’t wait—grab your ingredients and enjoy this festive, delicious treat today!

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