If you’re craving a treat that’s as fun to make as it is to eat, this Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe is an absolute showstopper. These adorable pumpkin-shaped cookies hide a gooey surprise of creamy milk chocolate inside, perfectly blending classic fall spices with a rich, melty center for a bite that’s pure joy. Whether you’re baking for a Halloween party or just want to fill your home with comforting aromas and smiles, this recipe combines delightful textures and flavors that’ll have everyone reaching for seconds.

Ingredients You’ll Need
These ingredients are simple yet essential, each bringing its own special touch to the cookies. From the warm spices that evoke cozy autumn vibes to the luscious butter and rich milk chocolate that create the perfect melt inside, every item is chosen to make your Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe unforgettable.
- Unsalted butter (1 ½ cups or 3 sticks): Room temperature butter ensures a smooth, creamy dough with great texture.
- Brown sugar (1 cup, packed): Adds moisture and a deep caramel flavor that complements the spices.
- Granulated sugar (½ cup): Balances sweetness and helps give the cookies a tender crumb.
- Large eggs (2): Bind the dough together while adding richness.
- Vanilla extract (1 tablespoon): Enhances all the flavors with a warm, sweet aroma.
- All-purpose flour (3 ¾ cups): The base of the dough, providing structure and the perfect chewy bite.
- Baking soda (1 teaspoon): Helps the cookies rise to just the right height.
- Ground cinnamon (1 teaspoon): Delivers cozy spice that’s a hallmark of fall desserts.
- Ground ginger (½ teaspoon): Adds a gentle heat and depth of flavor.
- Ground nutmeg (¼ teaspoon): Brings a warm, nutty fragrance to the mix.
- Salt (½ teaspoon): Balances sweetness and enhances the spices.
- Milk chocolate (12 oz, chopped or bars): The luscious creamy center that melts in your mouth.
- Cinnamon sugar (for dusting): Adds a final sparkle of sweetness and a touch of spice on top.
How to Make Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe
Step 1: Creaming the Butter and Sugars
Start off by beating the room-temperature butter with the brown and granulated sugars until the mixture is light, fluffy, and beautifully creamy—about 2 to 3 minutes. This step is key to achieving that melt-in-your-mouth texture. Then, add in the eggs one at a time to keep the mixture smooth, followed by the vanilla extract to infuse a lovely aromatic sweetness into your dough.
Step 2: Mixing the Dry Ingredients
In a separate bowl, whisk together your flour, baking soda, cinnamon, ginger, nutmeg, and salt. These spices bring that unmistakable autumn warmth to your cookies while the baking soda ensures they rise perfectly. Gradually add the dry mixture to your wet ingredients, mixing gently until a soft dough forms. Splitting the dough and chilling it helps in rolling out smooth, clean shapes for your Jack-O’-Lanterns.
Step 3: Cutting Out the Pumpkin Shapes
Preheat the oven to 350°F (175°C). On a lightly floured surface, roll your chilled dough to about ¼ inch thickness. Using a pumpkin-shaped cookie cutter, cut out as many cookies as possible. For the top half of your sandwiches, carefully cut out Jack-O’-Lantern faces with a knife or small cutters, giving your cookies that iconic spooky look. This step brings the recipe to life and makes it uniquely festive.
Step 4: Assembling the Stuffed Cookies
Place the uncut pumpkin cookies on a parchment-lined baking sheet and add a piece of milk chocolate in the center of each. Then top with the Jack-O’-Lantern face cut-outs, pressing the edges firmly to seal the chocolate inside. This delightful hidden center will surprise anyone who bites in!
Step 5: Baking and Finishing Touches
Bake the cookies for 10 to 12 minutes until they are lightly golden around the edges, signaling they are perfectly baked yet still soft inside. Once out of the oven, dust them with cinnamon sugar for that extra signature sparkle of sweetness and spice. Let the cookies cool for about 5 minutes on the baking sheet before transferring them to a rack to cool completely. This resting time allows the chocolate to set just enough for easy handling while maintaining its gooey charm.
How to Serve Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe

Garnishes
Enhance your Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe experience by sprinkling a little extra cinnamon sugar just before serving or adding a tiny drizzle of melted white chocolate for contrast. Freshly whipped cream or a dollop of pumpkin butter on the side makes each bite even more indulgent and festive.
Side Dishes
Pairing these cookies with a warm mug of spiced apple cider or a creamy pumpkin spice latte will truly elevate your taste buds to autumnal heaven. For a party, consider serving alongside a cheese platter with mild cheeses and fresh fruit to balance the sweetness.
Creative Ways to Present
Lay your Jack-O’-Lantern cookies on a rustic wooden board decorated with autumn leaves and tiny gourds for a charming fall centerpiece. For kids, you can set up a DIY decorating station with edible markers and colorful icing to personalize their spooky faces. Packaging them in clear cellophane bags tied with orange ribbon makes for a perfect treat to give away during Halloween festivities.
Make Ahead and Storage
Storing Leftovers
Keep any leftover Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe fresh by storing them in an airtight container at room temperature. They will stay delightful for up to 4 days, maintaining their soft texture and flavorful spices.
Freezing
If you want to prepare your cookies ahead of time or save some for later, freezing is a great option. Place cooled cookies in a single layer on a baking sheet for an hour, then transfer to a freezer-safe container or bag. Frozen cookies can last for up to 3 months. Just be sure to thaw them at room temperature before enjoying.
Reheating
To recapture that warm, melty chocolate feeling, pop your cookies in a 300°F oven for 5 to 7 minutes or warm them gently in the microwave for about 10 seconds. This quick reheating makes them taste just like fresh-baked, with gooey centers ready to delight.
FAQs
Can I use dark chocolate instead of milk chocolate?
Absolutely! Using dark chocolate will give your cookies a richer, slightly bitter contrast to the sweet and spicy dough, which many find delicious. Just be sure to chop it finely so it melts evenly inside the cookies.
What if I don’t have a pumpkin-shaped cookie cutter?
No worries! You can use any round or oval cookie cutter and create faces with a sharp knife for a similar Jack-O’-Lantern effect. Even freehand cutting adds a charming, homemade touch.
Can I make these cookies vegan or gluten-free?
With some ingredient swaps, yes! Use vegan butter and egg substitutes along with a gluten-free flour blend. Keep in mind this might slightly alter the texture, but the cookies will still be tasty and festive.
How do I keep the chocolate from leaking out during baking?
Pressing the edges firmly when sandwiching the cookies helps seal the chocolate inside. Chilling the dough before baking also reduces spreading, so the chocolate stays neatly tucked in.
Can I prepare the dough in advance?
Definitely! You can make the dough up to 2 days ahead and keep it wrapped in the fridge. Just bring it to a slightly softened state before rolling and cutting for best results in this Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe.
Final Thoughts
There’s something truly magical about biting into a cookie that has a melty milk chocolate surprise inside, especially when it’s dressed up like a cheerful Jack-O’-Lantern. This Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe combines warmth, sweetness, and festive fun all in one, making it a perfect treat to share well beyond Halloween. Trust me, once you try these, they’ll become a beloved tradition you’ll look forward to year after year!
Print
Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe
- Prep Time: 30 minutes
- Cook Time: 12 minutes
- Total Time: 42 minutes
- Yield: 24 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are festive, soft-spiced cookies perfect for Halloween. Filled with rich milk chocolate and decorated with cute Jack-O’-Lantern faces, they offer a delightful combination of warm spices and melty chocolate inside a tender cookie shell.
Ingredients
Cookie Dough
- 1 ½ cups (3 sticks) unsalted butter, room temperature
- 1 cup packed brown sugar
- ½ cup granulated sugar
- 2 large eggs
- 1 tablespoon vanilla extract
- 3 ¾ cups all-purpose flour
- 1 teaspoon baking soda
- 1 teaspoon ground cinnamon
- ½ teaspoon ground ginger
- ¼ teaspoon ground nutmeg
- ½ teaspoon salt
Filling and Topping
- 12 oz milk chocolate, chopped or use chocolate bars
- Cinnamon sugar (for dusting)
Instructions
- Prepare the Butter and Sugars: In a large bowl, beat the unsalted butter, brown sugar, and granulated sugar together until the mixture is light and fluffy, which usually takes about 2-3 minutes. This step creates a smooth base for your dough. Then add the eggs one at a time, beating well after each addition, followed by mixing in the vanilla extract until fully combined.
- Combine Dry Ingredients and Form Dough: In a separate bowl, whisk together the all-purpose flour, baking soda, ground cinnamon, ground ginger, ground nutmeg, and salt. Gradually add these dry ingredients to the wet mixture, stirring until a uniform dough forms. Divide the dough into two parts, tightly wrap each in plastic wrap, and chill in the refrigerator for at least 30 minutes or until firm enough to roll.
- Roll and Cut Cookies: Preheat your oven to 350°F (175°C). On a lightly floured surface, roll out one portion of chilled dough to about ¼-inch thickness. Using a pumpkin-shaped cookie cutter, cut out as many cookies as possible. For half of these cutouts, use a sharp knife or smaller cutters to carve Jack-O’-Lantern faces to create the top cookie layer.
- Assemble the Stuffed Cookies: Place the plain pumpkin-shaped cookies on a baking sheet lined with parchment paper. Place a piece of chopped milk chocolate or a small chunk of chocolate bar on the center of each plain cookie. Then carefully top with a Jack-O’-Lantern face cookie, pressing gently around the edges to seal the two halves together, enclosing the chocolate inside.
- Bake and Finish: Bake the assembled cookies in the preheated oven for 10-12 minutes or until they turn lightly golden on the edges. Once baked, immediately dust the cookies with cinnamon sugar while still warm. Let the cookies cool on the baking sheet for 5 minutes before removing them to a wire rack to cool completely.
Notes
- Ensure the dough is well chilled before rolling to prevent sticking and easier handling.
- Use good quality milk chocolate for the best melty center.
- Press cookies firmly when sealing to keep the chocolate from oozing out during baking.
- Store leftover cookies in an airtight container at room temperature for up to 5 days.

