Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe

If you’re looking for a Halloween treat that’s both fun and absolutely delicious, this Milk Chocolate Stuffed Jack-O’-Lantern Cookies recipe is a total winner. I love how the soft pumpkin-shaped cookies hold a surprise center of creamy milk chocolate that melts just a little when you bite in—makes it feel extra special and festive!

Whether you’re baking for a kid’s party, a cozy night with your family, or simply want to impress guests with a seasonal twist, these cookies nail it. The warm cinnamon and spices blend perfectly with the buttery dough, and the chocolate adds just the right touch of indulgence. Trust me, you’ll want to keep some hidden just for yourself!

this …

Ingredients You’ll Need

All the ingredients in this Milk Chocolate Stuffed Jack-O’-Lantern Cookies recipe come together to create a soft, buttery yet beautifully spiced cookie that melts in your mouth. The milk chocolate adds richness, and the cinnamon sugar coating on top gives that perfect sweet crunch.

• Salted butter: Use softened butter for creamy texture; it helps the dough come together nicely.
• Light brown sugar: Adds moisture and a subtle caramel flavor that lifts the cookies.
• Pure vanilla extract: You’ll love how this elevates the whole flavor profile.
• Eggs: Room temperature eggs help the dough bind evenly and create structure.
• All-purpose flour: The base for your cookies—makes them tender but sturdy.
• Baking soda: Gives your cookies a little lift and helps them stay soft.
• Cinnamon: The star spice in these cookies—it’s warm and comforting.
• Ginger: Adds a subtle zing that complements the cinnamon perfectly.
• Nutmeg: A pinch creates that authentic fall spice vibe.
• Salt: Balances sweetness and enhances flavor layers.
• Milk chocolate: Melted for stuffing, choose good-quality bars for the best melt and flavor.
• Cinnamon sugar: The final sprinkle for that addictive crunchy finish.

Variations

I like to switch things up sometimes to make this Milk Chocolate Stuffed Jack-O’-Lantern Cookies recipe fit the mood or dietary needs of whoever’s enjoying them. Playing with flavors or substitutions can be a fun way to make this recipe your own.

• Dark Chocolate or White Chocolate Filling: I swapped in dark chocolate once to give a richer bite, and it was a big hit with the adults!
• Gluten-Free Version: By using a gluten-free flour blend, you can easily adapt this recipe for gluten sensitivities without losing texture.
• Spice It Up: Adding a dash of cayenne or chili powder to the dough gives a little unexpected kick I love experimenting with.
• Vegan Adaptation: Try coconut oil instead of butter and flax eggs—it’s a bit of trial, but the results are rewarding.

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

Step 1: Cream, Mix, and Spice It Right

Start by creaming the butter, brown sugar, and vanilla together until it’s fluffy and beautifully light—this usually takes me 3 to 5 minutes with a stand mixer. Then, add the eggs one at a time, making sure each is well incorporated before the next. Next, you’ll add your dry ingredients: flour, baking soda, cinnamon, ginger, nutmeg, and salt. Beat just until it all comes together into a soft dough ball. Pro tip: don’t overmix here; too much beating can make the cookies tough.

Step 2: Rolling, Cutting, and Freezing for Perfect Shape

I like to generously flour my work surface and the rolling pin—that way the dough doesn’t stick and tearing is less likely. Divide the dough into two disks for easier handling and roll each one out to about 1/4-inch thickness. Use your pumpkin cookie cutter to stamp out shapes. For half of the cookies, carefully carve out eyes and a mouth using a small paring knife or a smaller cutter. Then freeze the cookie sheets for about 15-20 minutes—this step is a game-changer and helps the cookies keep their Jack-O’-Lantern details beautifully.

Step 3: Baking to Soft, Golden Perfection

Pop your cookies in a 350°F oven and bake on the middle rack for 8 to 12 minutes, depending on how soft you like them. You want them just lightly golden around the edges—don’t let them overbake or they’ll lose their signature softness. Give them five minutes on the sheet before moving to a wire rack to cool completely.

Step 4: Butter, Cinnamon Sugar, and the Melty Chocolate Magic

Here’s where things get ultra tasty: melt some butter in a medium pot and let it brown slightly—this adds a toasty richness that takes the cookie topping to another level. Brush this warm brown butter over the pumpkin-faced cookie halves, then sprinkle cinnamon sugar on top. For the other half of the cookies (the ones without faces), spread a generous layer of melted milk chocolate. Gently sandwich a face-covered cookie on top to complete your Jack-O’-Lantern. If you can resist, let the chocolate firm up before serving.

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

Garnishes

I like to dust a touch more cinnamon sugar right before serving for extra sparkle and sweetness. Sprinkling edible gold dust or a few festive orange and black sprinkles can make these cookies even more party-ready and kid-friendly—plus they catch the light beautifully on a dessert table.

Side Dishes

These cookies pair wonderfully with a warm cup of spiced chai, pumpkin latte, or even a creamy hot chocolate. For a Halloween party spread, they’re great alongside caramel apples, candied nuts, or simple fresh fruit to balance all that sweetness.

Creative Ways to Present

For a festive touch, I like arranging them in a circle on a dark platter to mimic a glowing jack-o’-lantern face or pile them in a rustic pumpkin basket lined with orange cellophane for an eye-catching display. You could also stack a few with parchment paper between layers in clear treat bags tied with a Halloween ribbon for gift-giving.

Make Ahead and Storage

Storing Leftovers

I store leftover cookies in an airtight container at room temperature for up to three days, keeping them soft and the chocolate filling nicely set without hardening. If your kitchen is warm, placing the container in a cool spot helps prevent the chocolate from melting too much.

Freezing

When I’ve made a big batch, I often freeze these cookies after baking but before adding the chocolate filling. That way, you can thaw and add the melted chocolate right before serving for the freshest taste and best-looking cookies.

Reheating

If you want to warm these up, I gently heat them in a preheated 300°F oven wrapped loosely in foil for 5 minutes to avoid melting the filling too much. It’s a nice way to revive that just-baked softness and chocolate gooeyness.

FAQs

Final Thoughts

This Milk Chocolate Stuffed Jack-O’-Lantern Cookies recipe has become one of my favorite fall traditions. There’s something so joyful about baking these cheerful pumpkins and sneaking a gooey, chocolate surprise inside. I hope you’ll love making (and eating) them as much as I do—they’re sure to add a little extra magic to your Halloween celebrations!

Print