If you’re looking for the ultimate fall treat that’s sure to charm every guest and make even the tiniest goblins smile, these Milk Chocolate Stuffed Jack-O’-Lantern Cookies will absolutely steal the show. Warmly spiced brown sugar cookies, each one hand-cut into cheerful little pumpkins, get a gooey milk chocolate center and a buttery dusting of cinnamon sugar. The result is a festive cookie that’s as decadent as it is whimsical—perfect for Halloween, Thanksgiving, or whenever you need a sweet pick-me-up with a touch of nostalgia.

Milk Chocolate Stuffed Jack-O'-Lantern Cookies Recipe - Recipe Image

Ingredients You’ll Need

You’ll be amazed at how approachable the ingredient list is—nothing too fancy, but each item plays a critical role in building the cookie’s flavor, texture, and adorable appearance. Every component is carefully chosen to create that perfect blend of soft cookie, spiced aroma, and luscious chocolate filling.

Salted butter, softened: Lends richness and a hint of salt, making the cookie dough beautifully tender and delicious.
Light brown sugar, packed: Gives the cookies their deep caramel notes and soft, chewy bite.
Pure vanilla extract: Adds fragrant warmth, enhancing both the spices and the chocolate.
Eggs, at room temperature: Binds everything together while keeping the cookies light and tender.
All-purpose flour: The sturdy backbone for cookies that hold their shape during baking and cutting.
Baking soda: Just enough lift for a soft texture without spreading too much.
Cinnamon: The heart of the cookie’s cozy autumn flavor profile.
Ginger: A gentle spicy zip that brightens and elevates the spice blend.
Nutmeg: Rounds out the spices for a wholly comforting aroma and flavor.
Salt: Balances the sweetness and brings out every subtle flavor note.
Milk chocolate, melted: The decadent core of each cookie, giving you that irresistible stuffed center.
Salted butter (for coating): Used to brush the baked cookies for a glossy, rich finish.
Cinnamon sugar: Sprinkled over the buttered tops to add crunch, sweetness, and sparkle.

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

Step 1: Cream the Butter and Sugar

Start by combining the softened butter, light brown sugar, and vanilla extract in a large mixing bowl. Beat them together on medium-high speed until the mixture is light, fluffy, and deliciously fragrant—this usually takes about 3 to 5 minutes. Next, add the eggs one by one, blending after each addition until the dough looks smooth and cohesive. This base is what gives your Milk Chocolate Stuffed Jack-O’-Lantern Cookies their supple texture and rich flavor.

Step 2: Mix the Dry Ingredients and Form the Dough

In a separate bowl, whisk together the flour, baking soda, cinnamon, ginger, nutmeg, and salt. Gradually add the dry mix into your wet ingredients, beating just until combined. When the dough starts to pull together into a ball and smells like the best day of autumn, you know you’re ready to move on. Divide the dough in half and shape each half into a disk—this helps it chill faster and roll out more evenly.

Step 3: Roll, Cut, and Chill the Cookies

Generously flour your work surface, then roll out each disk to a quarter-inch thickness. Using a pumpkin cookie cutter, stamp out as many pumpkins as you can. For that classic jack-o’-lantern look, cut eyes and a mouth into half of the cookies—these will form the cookie tops. Arrange all the cookies onto parchment-lined baking sheets, cover lightly, and pop them into the freezer for 15 to 20 minutes. This step keeps the cookies sharp-edged and easy to handle.

Step 4: Bake to Perfection

Preheat your oven to 350 degrees. Slide the trays into the middle oven rack and bake for 8 to 12 minutes, depending on how soft you love your cookies. Keep an eye out for just a hint of golden brown around the edges. Once done, let them rest on the baking sheet for 5 minutes before transferring to a wire rack—this prevents any accidental breakage and ensures lovely, tender cookies every time.

Step 5: Brown the Butter and Add Cinnamon Sugar

In a small pot, melt the remaining salted butter and let it cook just until it browns and smells nutty, about 2 to 3 minutes. This adds a depth of flavor you’ll notice with every bite! Let it cool briefly, then brush it over the tops of your pumpkin-shaped cookies (the ones with faces). Generously sprinkle each one with cinnamon sugar while the butter is still wet for that perfect sweet crunch.

Step 6: Stuff with Milk Chocolate and Assemble

The crowning touch: slather a generous layer of melted milk chocolate onto the cookie bottoms (the ones without faces), then gently pair each with a cinnamon-sugar-dusted pumpkin face. Give them a gentle press to seal in all that melty goodness. Enjoy immediately if you simply cannot wait, or let the chocolate set for a sandwich cookie that travels and stores beautifully.

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

Garnishes

You can absolutely lean into the whimsy by adding a tiny green candy or fondant “stem” at the top of each jack-o’-lantern, or dust the plate with extra cinnamon sugar just before serving. Edible gold dust or a drizzle of white chocolate can also make these stand out for more elegant affairs.

Side Dishes

Pair these cookies with a cozy mug of hot cider, spiced hot chocolate, or even a mildly sweet chai. For parties, serve alongside a platter of fresh apple slices or a bowl of roasted nuts for crunch—you want something to balance the luxurious sweetness of your Milk Chocolate Stuffed Jack-O’-Lantern Cookies.

Creative Ways to Present

Stack the finished cookies in a rustic wooden tray for a farmhouse-style vibe, or arrange them in neat rows on a dark slate platter for dramatic effect at Halloween parties. Individual cellophane bags tied with orange ribbon make fantastic party favors, and you can even nestle a few into a festive cookie tin for a delightful seasonal gift.

Make Ahead and Storage

Storing Leftovers

Milk Chocolate Stuffed Jack-O’-Lantern Cookies hold up wonderfully for up to three days in an airtight container at room temperature. The filling sets just enough to stay put, and the spices meld together with the butter and brown sugar, meaning the cookies taste even better the next day.

Freezing

If you want to make these beauties ahead, assemble and freeze the unbaked, cut-out cookies between layers of parchment paper. Bake from frozen, adding a minute or two to the oven time. Or, freeze fully assembled cookies (once the chocolate has set), and thaw at room temperature for a perfect treat any time.

Reheating

To refresh cookies for serving, warm them for just 5 to 10 seconds in the microwave, or pop them into a 300-degree oven for a few minutes. This brings back that dreamy chocolate melt and makes the spiced aroma irresistible all over again.

FAQs

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

Absolutely! Dark chocolate adds a richer, slightly bittersweet flavor, while white chocolate brings extra creaminess. Just make sure to melt it gently and proceed exactly as with the milk chocolate for that oozy stuffed center.

What can I do if I don’t have a pumpkin cookie cutter?

No problem! Use any round cutter you have, then press in lines with a knife to mimic pumpkin ridges. You can also freehand the faces for maximum charm and originality—imperfections make these cookies even more lovable.

How do I keep the cookies from spreading or losing shape?

Chilling the cut-out dough thoroughly before baking is key! Placing the baking sheets in the freezer for 15 to 20 minutes ensures sharp edges and neat shapes, especially when making detailed faces for your Milk Chocolate Stuffed Jack-O’-Lantern Cookies.

Can these cookies be made gluten-free?

Yes! Substitute your favorite 1:1 gluten-free flour blend for regular all-purpose flour. Keep an eye on dough texture—the result should be soft but not sticky, and chilling is even more important to help gluten-free doughs hold their shape.

What’s the best way to melt the chocolate for stuffing?

Use a microwave-safe bowl and heat in short 20- to 30-second bursts, stirring between each until smooth. Or, melt the chocolate in a heatproof bowl set over a pot of simmering water. Just be patient, and your Milk Chocolate Stuffed Jack-O’-Lantern Cookies will have a glossy, dreamy chocolate core.

Final Thoughts

There’s just something magical about baking and sharing these Milk Chocolate Stuffed Jack-O’-Lantern Cookies—every step is a joy, and the finished result never fails to impress both kids and adults alike. Whether you’re getting ready for a spooky celebration or just want to bring a little extra warmth to your kitchen, give these cookies a try and delight in every gooey, chocolate-stuffed bite!