Name: Milk Chocolate Stuffed Jack-O’-Lantern Cookies
Prep time: 20 min
Cook time: 12 min
Total time: 35 min
Cuisine: American
Ingredients: 1 cup unsalted butter, softened; 1 cup brown sugar; 1/2 cup granulated sugar; 1 large egg; 2 teaspoons vanilla extract; 2 1/2 cups all-purpose flour; 1 teaspoon baking soda; 1 teaspoon ground cinnamon; 1/2 teaspoon ground nutmeg; 1/2 teaspoon ground ginger; 1/4 teaspoon salt; Milk chocolate squares or bars (enough for 12 sandwich cookies); Cinnamon sugar mixture (for dusting)

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These milk chocolate stuffed jack-o’-lantern cookies are festive, spiced treats perfect for fall celebrations. Soft brown sugar cookies are sandwiched together with a creamy milk chocolate filling, then dusted with cinnamon sugar for just the right touch of sweetness.

Why You’ll Love This Recipe

I love how these cookies combine cozy fall flavors with a fun seasonal twist. The spiced brown sugar cookies are soft and chewy, while the melted milk chocolate in the center adds a rich surprise. I enjoy carving out the jack-o’-lantern faces, which makes them as fun to look at as they are to eat. They’re perfect for Halloween, Thanksgiving, or any time I want a festive dessert. Milk Chocolate Stuffed Jack-O’-Lantern Cookies

ingredients

(Here’s a tip: Check out the full list of ingredients and measurements in the recipe card below.)

Unsalted butter
Brown sugar
Granulated sugar
Egg
Vanilla extract
All-purpose flour
Baking soda
Ground cinnamon
Ground nutmeg
Ground ginger
Salt
Milk chocolate squares or bars (for the filling)
Cinnamon sugar mixture (for dusting)

directions

I cream together the butter, brown sugar, and granulated sugar until light and fluffy.
I beat in the egg and vanilla extract until smooth.
In a separate bowl, I whisk flour, baking soda, cinnamon, nutmeg, ginger, and salt. I add this dry mixture to the wet ingredients and mix until just combined.
I roll out the dough on a floured surface and cut out pumpkin shapes using a cookie cutter.
On half of the cutouts, I carve little jack-o’-lantern faces with a small sharp knife.
I place a piece of milk chocolate in the center of the plain pumpkin cutouts, then top with a jack-o’-lantern face cutout, pressing edges to seal.
I transfer the cookies to a baking sheet and bake at 350°F (175°C) for 10–12 minutes until golden around the edges.
While warm, I dust them lightly with cinnamon sugar before letting them cool.

Servings and timing

This recipe makes about 12 sandwich cookies, depending on cutter size. It takes about 20 minutes to prep and 12 minutes to bake, so I can have them ready in around 35 minutes. Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Variations

I sometimes use dark chocolate or white chocolate instead of milk chocolate for a different flavor. For an extra indulgent version, I add a thin layer of caramel along with the chocolate filling. If I want a simpler cookie, I skip the jack-o’-lantern carving and just make them into chocolate-filled sandwich cookies.

storage/reheating

I store these cookies in an airtight container at room temperature for up to 4 days. For longer storage, I freeze them for up to 2 months. When I want one, I let it thaw at room temperature or warm it briefly in the microwave for a melty center.

FAQs

Do I have to carve faces into the cookies?

No, I sometimes leave them plain for a quicker version, but the jack-o’-lantern faces make them festive and fun.

Can I use pre-made cookie dough?

Yes, I can use store-bought sugar cookie dough as a shortcut, though the flavor won’t be as spiced as homemade.

What type of chocolate works best?

I prefer milk chocolate for sweetness, but dark chocolate adds richness, and white chocolate makes them extra sweet and creamy.

Can I make the dough ahead of time?

Yes, I chill the dough for up to 2 days before baking, which also makes it easier to roll and cut.

How do I keep the cookies from spreading too much?

I chill the cut cookies on the baking sheet for 10–15 minutes before baking to help them hold their shape.

Conclusion

I find these milk chocolate stuffed jack-o’-lantern cookies to be the perfect mix of festive fun and indulgence. They’re warm, spiced, and filled with gooey chocolate that makes them irresistible. Whether I serve them at a Halloween party or as a cozy fall dessert, they always disappear quickly.