Let’s be honest. Halloween is 50% costumes and 50% sweets. Every year, I try to bake something new, something that makes people pause mid-bite and say, “Wait, you made this?!” Shaym here from SoolFood, and this year’s winner might just be these Milk Chocolate Stuffed Jack-O-Lantern Cookies.
They’re crispy around the edges, soft in the center, and filled with melty milk chocolate that oozes out when warm. But the real showstopper? The jack-o-lantern cutouts on top. These cookies look like little pumpkin faces glowing with chocolate. A treat that doubles as edible Halloween décor.
These cookies come together with a simple sugar cookie dough, but you’ll need a pumpkin-shaped cutter and a tiny knife or cutter for the faces. Don’t worry, even if they’re a little imperfect, that only adds to the spooky charm. And once that milk chocolate filling starts peeking through? Instant magic.
I love serving these on a platter alongside Halloween Brownies and a few Easy Halloween Party Treats. They’re also perfect for classroom parties, cookie swaps, or a Halloween movie night.
And if you’re into fun textures, try pairing them with our Chocolate Chip Rice Krispie Cookies. Trust me, there won’t be a single crumb left.
🎃 Milk Chocolate Stuffed Jack-O-Lantern Cookies Recipe
Prep Time: 30 mins
Chill Time: 1 hour
Bake Time: 10–12 mins
Yield: 12–14 sandwich cookies
🧂 Ingredients:
- 2 ½ cups all-purpose flour
- ½ teaspoon baking powder
- ¼ teaspoon salt
- 1 cup (2 sticks) unsalted butter, softened
- ¾ cup granulated sugar
- 1 egg
- 1 teaspoon vanilla extract
- 1 cup milk chocolate chips or chopped chocolate
- 1 teaspoon coconut oil (optional, for smoother chocolate)
🥄 Instructions:
- Make the dough
In a bowl, whisk together flour, baking powder, and salt. In a separate bowl, beat butter and sugar until light and fluffy (about 2–3 mins). Add egg and vanilla; mix until combined. Gradually add the dry ingredients until dough forms. - Chill the dough
Divide dough in half, flatten into discs, and wrap in plastic. Chill in the fridge for at least 1 hour. - Roll and cut
Preheat oven to 350°F (175°C). On a floured surface, roll out dough to about ⅛ inch thick. Use a pumpkin-shaped cookie cutter to cut out shapes. On half of the cookies, carve jack-o-lantern faces using a small knife or cutter. - Bake
Place cookies on a parchment-lined sheet. Bake for 10–12 minutes or until edges are lightly golden. Let cool completely. - Make the filling
Melt chocolate and coconut oil together in a microwave-safe bowl in 20-second bursts until smooth. - Assemble
Spread or pipe a dollop of melted chocolate on each full pumpkin cookie (no face). Top with a jack-o-lantern face cookie and gently press to sandwich. - Set and serve
Let the chocolate set at room temperature or refrigerate for faster results. Store in an airtight container for up to 5 days.
These Milk Chocolate Stuffed Jack-O-Lantern Cookies aren’t just cookies. They’re an experience. Fun to make, fun to eat, and perfect for the season. Bake a batch, share a few, and save one (or two) for yourself.