Milk Chocolate Stuffed Jack-O’-Lantern Cookies are a fun and easy Halloween treat. These cookies have soft spiced dough, a creamy milk chocolate filling, and a cute pumpkin shape. They look festive, taste sweet and buttery, and are perfect for sharing during the fall season.
Why We Love This Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe
There’s something special about a cookie that looks like it came straight from a fall-themed bakery, but was made right in your kitchen. You’ll love this recipe because it’s easy enough to follow yet produces impressive results. The cookie base is soft, buttery, and filled with warming spices like cinnamon, ginger, and nutmeg. These flavors pair beautifully with the milk chocolate center, which stays slightly melty even after cooling.
The real charm comes in the shape. Pumpkin cut-outs with carved eyes and toothy smiles give these cookies an eye-catching finish that makes them perfect for Halloween gatherings. They also make thoughtful edible gifts when wrapped up with ribbon. And unlike many holiday treats that can be overly sweet, these cookies strike the perfect balance between sugar, spice, and chocolate.
From the smell in your kitchen while they bake to the smile on someone’s face when they bite in, these cookies deliver comfort and joy in every step. They’re as fun to look at as they are to eat—and that’s something to love.
Ingredients about Milk Chocolate Stuffed Jack-O’-Lantern Cookies
- 1 ½ cups (3 sticks) salted butter, softened
- 1 ¼ cups packed light brown sugar
- 1 tablespoon pure vanilla extract
- 2 eggs, at room temperature
- 4 ½ cups all-purpose flour
- 1 teaspoon baking soda
- 1 teaspoon ground cinnamon
- ½ teaspoon ground ginger
- ¼ teaspoon ground nutmeg
- ½ teaspoon salt
- 12 ounces milk chocolate, melted
For the cinnamon sugar coating:
- 2 tablespoons salted butter
- 3 tablespoons cinnamon sugar
With this lineup, you’ll create a dough that’s rich and flavorful, and a filling that’s smooth and creamy. These ingredients give each cookie a bakery-style texture with a homemade touch.
How to Make Milk Chocolate Stuffed Jack-O’-Lantern Cookies Directions
Start by preparing the dough. In a large mixing bowl, cream together the softened butter and brown sugar. You want this mixture to become light and fluffy, which usually takes around 3 to 5 minutes of mixing. Add in the vanilla extract, then beat in the eggs one at a time until everything is well blended.
Now it’s time to add the dry ingredients. Slowly mix in the flour, baking soda, cinnamon, ginger, nutmeg, and salt. Blend until the dough comes together and forms a smooth, manageable ball. You should be able to press it without it sticking too much to your fingers.
Once your dough is ready, divide it in half and shape each half into a flat disk. Generously flour your surface and roll the dough to about ¼ inch thickness. Keep the surface floured to prevent sticking.
Use a pumpkin cookie cutter to cut out as many cookies as possible from the first rolled dough. For half of the cutouts, carefully carve out eyes and a mouth using a small paring knife or a smaller cutter—these will be your Jack-O’-Lantern faces.
Place all cookies onto a parchment-lined baking sheet, cover, and freeze for about 15–20 minutes. This helps the cookies hold their shape while baking. Meanwhile, roll out the remaining dough scraps and repeat the cutting and freezing steps.
While the cookies chill, preheat your oven to 350°F (175°C). Bake on the middle oven rack for about 8–12 minutes. The cookies should be slightly golden at the edges but still soft. Avoid overbaking for the best texture. Let them cool on the baking sheet for a few minutes before moving them to a wire rack.
While they’re cooling, prepare the cinnamon sugar coating. Melt the 2 tablespoons of butter in a pan over medium heat, allowing it to slightly brown for a toasted aroma—this takes about 2–3 minutes. Remove from heat and let it cool slightly.
Brush the browned butter over the carved face cookies only. Then, sprinkle with cinnamon sugar until lightly coated.
To assemble, take the uncut cookies and spread a spoonful of melted milk chocolate over each one. Top with a Jack-O’-Lantern face cookie, pressing gently to secure. You can serve them right away, or let them sit until the chocolate firms up.
Now you’ve got festive cookies with a fun twist—rich, warm, and filled with gooey chocolate.
How to Serve Milk Chocolate Stuffed Jack-O’-Lantern Cookies
These cookies are best served at room temperature when the chocolate is soft enough to bite into but not messy. They make a wonderful dessert for Halloween parties, fall festivals, or cozy nights at home. Arrange them on a large wooden board with orange slices, caramel popcorn, and spiced apple cider for a complete fall dessert spread.
You can also place them individually in small treat bags with a festive tag for party favors or gifts. If you’re hosting a Halloween-themed event, use these cookies as edible place cards by piping names on them with icing. No matter how you serve them, they’re guaranteed to get attention for both their appearance and flavor.
Expert Tips: Milk Chocolate Stuffed Jack-O’-Lantern Cookies
- Chill the dough before cutting and baking to help the cookies hold their shape. If you skip this step, the details of the pumpkin face might melt away in the oven.
- Use good-quality milk chocolate for the filling. It makes a big difference in taste and texture. You want chocolate that melts smoothly and stays creamy after baking.
- Avoid overbaking the cookies. They should come out just slightly golden at the edges and still soft in the center. This keeps them tender and gives a nice contrast to the crisp edges.
- Re-roll scraps gently. When working with leftover dough, try not to overwork it. Too much handling can make the cookies tough.
- Experiment with faces. If you’re feeling artistic, try creating different expressions for each Jack-O’-Lantern. Silly, spooky, or surprised faces make the batch more fun.
- Add a little spice to the chocolate. For a twist, mix a pinch of cinnamon or chili powder into the melted chocolate before assembling the cookies. It adds an unexpected warmth.
How to Store Milk Chocolate Stuffed Jack-O’-Lantern Cookies
To keep your cookies fresh, store them in an airtight container at room temperature. They will stay good for up to 3 days. If your kitchen is particularly warm, you might want to store them in the fridge to prevent the chocolate from melting.
If you’re making them ahead, you can also freeze the baked cookies (without the chocolate) and then fill and decorate them closer to serving time. Just make sure they’re completely cool before freezing and separate the layers with parchment paper.
Variation of Milk Chocolate Stuffed Jack-O’-Lantern Cookies
There are several ways you can tweak this recipe to make it your own. One easy swap is to use dark or white chocolate instead of milk chocolate for the filling. Each brings a different taste and color that can change the mood of your cookies.
You can also flavor the dough differently—try adding a bit of orange zest for a citrusy kick or swap out the ginger for cardamom for a more exotic twist. For a slightly crunchier texture, sprinkle the inside with chopped nuts or crushed graham crackers before sealing the cookies.
Not in the mood for a face design? Simply cut circles or leaf shapes and turn these into spiced sandwich cookies. The same rich flavor, with less effort on decoration. You can even skip the filling and enjoy the cookies plain with a hot drink on the side.
FAQ – Milk Chocolate Stuffed Jack-O’-Lantern Cookies
What’s the best chocolate to use for stuffing these cookies?
You’ll get the creamiest results with a smooth milk chocolate bar that melts easily. Avoid chocolate chips unless they’re labeled as good for melting.
Can I make the dough ahead of time?
Yes, you can make the dough up to 2 days in advance and store it tightly wrapped in the fridge. You can also freeze it for longer storage.
Do I need a pumpkin cookie cutter?
It helps, but it’s not required. You can use a round cutter and then carve the pumpkin face with a paring knife.
Can I use unsalted butter?
Yes, but add an extra ¼ teaspoon of salt to the dough to balance the flavors.
Why are my cookies spreading too much in the oven?
This usually happens if the dough wasn’t chilled enough before baking. Make sure to freeze or refrigerate the cutouts before they go into the oven.
How do I keep the chocolate from leaking out?
Don’t overfill. Spread the chocolate neatly in the center and leave a small edge around the cookie so it doesn’t spill out when pressed together.
Are these cookies safe for kids to help make?
Absolutely! Kids will love cutting out the shapes and decorating the faces. Just be sure an adult handles the hot melted chocolate and oven steps.
Milk Chocolate Stuffed Jack-O’-Lantern Cookies
Equipment
- Mixing Bowl
- Pumpkin Cookie Cutter
- Baking Sheet
Ingredients
- 1 1/2 cups salted butter (3 sticks, softened)
- 1 1/4 cups packed light brown sugar
- 1 tablespoon pure vanilla extract
- 2 large eggs (at room temperature)
- 4 1/2 cups all-purpose flour
- 1 teaspoon baking soda
- 1 teaspoon ground cinnamon
- 1/2 teaspoon ground ginger
- 1/4 teaspoon ground nutmeg
- 1/2 teaspoon salt
- 12 ounces milk chocolate (melted)
- 2 tablespoons salted butter (for coating)
- 3 tablespoons cinnamon sugar
Instructions
- In a large mixing bowl, cream together softened butter and brown sugar until light and fluffy.
- Add vanilla extract and beat in eggs one at a time until well blended.
- Gradually mix in flour, baking soda, cinnamon, ginger, nutmeg, and salt until a smooth dough forms.
- Divide dough in half, shape each half into a disk, and roll out to ¼ inch thickness on a floured surface.
- Use a pumpkin cookie cutter to cut out cookies, carving faces on half of them for Jack-O’-Lanterns.
- Place cookies on a parchment-lined baking sheet, cover, and freeze for 15–20 minutes.
- Preheat oven to 350°F (175°C) and bake cookies for 8–12 minutes until slightly golden.
- Cool cookies on the baking sheet for a few minutes before transferring them to a wire rack.
- Melt 2 tablespoons of butter in a pan until slightly browned; let cool slightly.
- Brush browned butter over carved face cookies and sprinkle with cinnamon sugar.
- Spread melted milk chocolate over uncut cookies, then top with carved cookies to assemble.
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