Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe

I absolutely love sharing this Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe because it brings such a festive, playful twist to traditional cookie baking. When Halloween rolls around, these pumpkin-shaped treats filled with creamy milk chocolate are always a showstopper at my family gatherings. The combination of warm spices in the dough with that smooth chocolate center is just irresistible, making every bite a perfect balance of comforting and fun.

You’ll find that this Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe is not only delicious but also surprisingly straightforward, which I know is a huge plus when you’re juggling holiday preparations. Plus, the cinnamon sugar coating adds a little extra magic you didn’t even know you needed. Whether you’re baking with kids or want to impress guests with something a touch unique, these cookies are definitely worth trying this season.

this …

Ingredients You’ll Need

Each ingredient in this Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe plays a special role—highlighting classic autumn flavors and creating that soft, tender texture you want from a homemade cookie. Having quality salted butter and fresh spices makes all the difference, so I always make sure to get the best I can.

• Salted butter: Softened, it’s the base for our dough and adds rich flavor and tenderness.
• Light brown sugar: Packed for moisture and subtle caramel sweetness.
• Pure vanilla extract: Enhances the overall warmth and depth of the dough.
• Eggs: At room temperature to help the dough bind and achieve the right crumb.
• All-purpose flour: The structure of our cookies, so use a reliable brand you trust.
• Baking soda: Helps the cookies rise just enough to be soft and chewy.
• Cinnamon: The star spice for that classic cozy fall feel.
• Ginger: Adds a subtle bite and warmth.
• Nutmeg: Complements the cinnamon and ginger for a full autumn spice profile.
• Salt: Balances all the sweetness and spices beautifully.
• Milk chocolate: Melted for the creamy center, bringing sweetness and melt-in-your-mouth goodness.
• Cinnamon sugar: For that perfect final sprinkle on your cookies.

Variations

I love how versatile this Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe can be, so feel free to get creative with flavors and shapes depending on your mood or season. I sometimes swap the milk chocolate for dark chocolate or add a pinch of cayenne for an unexpected kick.

• Chocolate swap: Using semi-sweet or dark chocolate gives a richer, less sweet center that some of my friends prefer for adult tastes.
• Spice mix: Try adding a bit of ground cloves or cardamom for a unique twist on the classic autumn spices.
• Dairy-free version: Replace butter with plant-based alternatives and use dairy-free chocolate to accommodate dietary needs easily.
• Shape hack: If you don’t have a pumpkin cutter, I’ve successfully used circle cutters and hand-cut faces with a sharp knife—still adorable!

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

Step 1: Cream Butter, Sugar and Add Eggs

Start by beating the softened butter, light brown sugar, and vanilla together until it’s light and fluffy—this usually takes about 3-5 minutes with a mixer. This step is crucial because it incorporates air, making your cookies tender instead of dense. Then add the eggs one at a time, mixing well after each one to keep the texture even.

Step 2: Mix Dry Ingredients and Form Dough

In a separate bowl, whisk the flour, baking soda, cinnamon, ginger, nutmeg, and salt together. Slowly add the dry ingredients to your butter-sugar mixture and beat until a soft dough comes together. It should feel slightly firm but pliable enough to roll out — if it’s sticky, sprinkle a little more flour on your surface.

Step 3: Roll, Cut, and Freeze

Generously flour your work surface and roll half the dough into a 1/4-inch thickness. I’ve learned to use plenty of flour here because the dough can stick, and that’s frustrating when cutting out your pumpkin shapes. Use a pumpkin cookie cutter to cut out the shapes, and then create jack-o’-lantern faces on half the cookies with a pairing knife. Place cookies on a parchment-lined sheet and freeze for about 15-20 minutes to firm up — this helps them keep their shape and not spread too much during baking.

Step 4: Bake Until Just Golden

Preheat your oven to 350°F (175°C). Bake the cookies on the middle rack for 8-12 minutes, but watch carefully — you want soft edges with just a hint of golden brown. Overbaking will make them crispier, which isn’t the goal here since the stuffed chocolate center needs a bit of softness to shine.

Step 5: Brown Butter, Coat Cookies, and Assemble

While the cookies cool, gently brown the butter in a medium pot until it smells toasted—around 2-3 minutes. Brush this butter over the top halves of the cookies, then sprinkle the cinnamon sugar on top. Spread melted milk chocolate on the bottom halves without faces, then sandwich the pumpkin-faced cookies on top, pressing gently to stick the chocolate layer. Let them sit a bit for the chocolate to firm, or enjoy them immediately if you’re impatient like me!

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

Garnishes

I often garnish these cookies with a simple dusting of extra cinnamon sugar just before serving for a little sparkle and crunch. If I’m feeling extra festive, I sometimes drizzle a bit of white chocolate for contrast—it’s such a crowd-pleaser and makes the faces pop visually.

Side Dishes

Pair these cookies with a warm cup of spiced apple cider or a rich hot chocolate for the ultimate cozy autumn treat. They also go surprisingly well with a mild cream cheese frosting dip if you want to boost the indulgence factor.

Creative Ways to Present

One of my favorite ways to serve these Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe is on a rustic wooden board surrounded by mini pumpkins and autumn leaves for a festive centerpiece. I’ve also packaged them in clear cellophane bags tied with orange and black ribbons as adorable gifts for neighbors or coworkers!

Make Ahead and Storage

Storing Leftovers

Store these cookies in an airtight container at room temperature, layering them with parchment so they don’t stick together. They stay fresh for up to 3 days—which is perfect because, honestly, they tend to disappear faster in my house. Keep them away from humidity for best texture.

Freezing

If you want to freeze them, I recommend assembling the cookie sandwiches first, then wrapping them individually in plastic wrap before placing in a freezer-safe container. When ready to enjoy, just thaw them at room temperature for about an hour, and the chocolate gets melty again just like fresh.

Reheating

To warm up leftovers, pop the cookies in the microwave for 10-15 seconds or place briefly in a low-temp oven. This softly reactivates the chocolate center and revives that just-baked freshness—but don’t overdo it or the cookies may become too soft.

FAQs

Final Thoughts

This Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe has become a favorite tradition in my kitchen, partly because it’s both charming and downright delicious. I hope you enjoy baking them just as much as I do—there’s something special about making cookies that bring a little extra joy and festive spirit to your day. So grab your cookie cutters, melt that chocolate, and let’s get cozy with these pumpkin treats!

Print