Name: Milk Chocolate Stuffed Jack-O-Lantern Cookies Recipe
Prep time: 25 min
Cook time: 12 min
Total time: 1 h 10 min
Cuisine: American
Ingredients: 1 1/2 cups (3 sticks) salted butter, softened; 1 1/4 cups light brown sugar, packed; 1 tablespoon pure vanilla extract; 2 large eggs, at room temperature; 4 1/2 cups all-purpose flour; 1 teaspoon baking soda; 1 teaspoon cinnamon; 1/2 teaspoon ginger; 1/4 teaspoon nutmeg; 1/2 teaspoon salt; 12 oz milk chocolate, melted; 2 tablespoons butter (for cinnamon sugar topping); Cinnamon sugar (for sprinkling)

Jump to Recipe

There is something utterly magical about making Milk Chocolate Stuffed Jack-O-Lantern Cookies that instantly brings the spirit of the season right into your kitchen. These delightful treats combine perfectly spiced pumpkin-shaped cookies with a rich, creamy milk chocolate center that melts in your mouth with every bite. Whether you’re baking for a festive gathering or just because, these cookies offer a charming blend of cozy autumn flavors and playful Halloween fun that’s sure to impress both kids and adults alike.

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

Ingredients You’ll Need

Each ingredient in this recipe plays a crucial role, working together to build a cookie that is tender, flavorful, and irresistibly chocolaty. From the buttery richness to the warming spices, every element elevates the experience of these Milk Chocolate Stuffed Jack-O-Lantern Cookies.

1 1/2 cups (3 sticks) salted butter, softened: Provides richness and helps achieve a tender cookie texture.
1 1/4 cups light brown sugar, packed: Adds moisture, sweetness, and a hint of caramel depth.
1 tablespoon pure vanilla extract: Enhances all the flavors with a warm, fragrant note.
2 large eggs, at room temperature: Binds ingredients together and helps create a soft crumb.
4 1/2 cups all-purpose flour: The base structure for your cookies, offering just the right firmness.
1 teaspoon baking soda: A leavening agent that keeps the cookies light.
1 teaspoon cinnamon: Infuses that unmistakably cozy, autumn spice.
1/2 teaspoon ginger: Adds a gentle zing that lifts the warmth of the spices.
1/4 teaspoon nutmeg: Provides a subtle earthiness that complements the other spices.
1/2 teaspoon salt: Balances sweetness and enhances all other flavors.
12 oz milk chocolate, melted: The luscious center that makes these cookies unforgettable.

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

Step 1: Prepare the Dough

Start by creaming the softened butter and brown sugar until light and fluffy, which takes about 3 to 5 minutes—this step is key for light, tender cookies. Stir in pure vanilla extract, then beat in the eggs one at a time to fully incorporate them. Slowly add the flour, baking soda, cinnamon, ginger, nutmeg, and salt. Stir gently until the dough forms a nice, cohesive ball; if it feels sticky, don’t hesitate to sprinkle on a bit more flour as needed.

Step 2: Roll and Cut the Cookies

Flour your work surface generously and divide the dough into two halves, flattening each into a disk. Roll the dough out to about 1/4-inch thickness, flouring as you go to prevent sticking. Use your pumpkin-shaped cookie cutter to cut out plenty of dough shapes. For half of these, carefully carve jack-o-lantern faces using a pairing knife or small cutters—let your creativity shine here! Transfer the cookies to a parchment-lined baking sheet and freeze them for 15 to 20 minutes to keep their shape during baking.

Step 3: Bake the Cookies

Preheat your oven to 350°F (175°C). Once heated, place the chilled cookie sheets on the center rack and bake for 8 to 12 minutes. Look for lightly golden edges as a sign that they are perfectly baked. Let them cool on the sheet for about 5 minutes before moving the cookies to a wire rack to cool completely—handling them carefully so those delicate jack-o-lantern faces stay intact.

Step 4: Prepare the Cinnamon Sugar Topping

For an extra layer of flavor, melt two tablespoons of butter over medium heat until it turns a lovely golden brown and fills your kitchen with a toasted aroma—about 2 to 3 minutes. After it cools slightly, brush this browned butter over the jack-o-lantern face cookies, then sprinkle with cinnamon sugar. This adds a tantalizing sweet spice that is the perfect complement to the chocolate center.

Step 5: Assemble the Milk Chocolate Stuffed Jack-O-Lantern Cookies

Spread the melted milk chocolate generously on the flat, non-face cookies, then gently press a decorated jack-o-lantern face cookie on top of each one. This sandwich of cookie and milk chocolate is what makes these treats truly special. Let the chocolate set fully before serving to enjoy the perfect texture and flavor fusion.

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

Garnishes

Adding a touch of festive garnish can elevate your presentation. Consider a dusting of powdered sugar to mimic autumn’s first frost or a drizzle of white chocolate for a contrast that looks like moonlight on a dark night. Fresh mint leaves or a sprinkle of crushed nuts can also add color and texture, creating an enticing visual and flavor contrast.

Side Dishes

Serve these cookies alongside warm spiced apple cider or creamy pumpkin spice latte to keep your taste buds cozy. A scoop of vanilla ice cream or whipped cream on the side also pairs beautifully, balancing the richness of the chocolate and spices with a refreshing creaminess.

Creative Ways to Present

To impress guests, arrange the Milk Chocolate Stuffed Jack-O-Lantern Cookies on a tiered cake stand dressed with autumn leaves, miniature pumpkins, and candles. For a playful touch at a Halloween party, nestle them inside hollowed-out mini pumpkins or use decorative plates shaped like skulls and bats to set a spooky yet sweet scene.

Make Ahead and Storage

Storing Leftovers

Leftover Milk Chocolate Stuffed Jack-O-Lantern Cookies keep wonderfully in an airtight container for up to a week at room temperature. Store them in a cool place away from direct sunlight to maintain their texture and prevent the chocolate from melting.

Freezing

If you want to prepare these cookies in advance, freeze the fully assembled cookie sandwiches in a single layer on a baking sheet. Once frozen, transfer them to a freezer-safe container or bag. They can be kept frozen for up to three months without losing their delightful flavor or texture.

Reheating

To enjoy the cookies warm, let frozen cookies thaw overnight at room temperature, then warm them gently in a 300°F oven for 5-7 minutes. This refreshes the cookie’s softness and softly melts the chocolate center, creating a gooey, irresistible treat all over again.

FAQs

Can I use dark chocolate instead of milk chocolate for the filling?

Absolutely! Dark chocolate will add a deeper, slightly bitter note that pairs nicely with the subtle spices in the cookie. Just melt it the same way and enjoy a more intense chocolate experience.

Do these cookies need to be refrigerated?

They don’t require refrigeration if you plan to eat them within a week. However, if your home is very warm, keeping them in the fridge can help prevent the chocolate from melting too much.

Can I make the cookie dough ahead of time?

Yes! The dough can be refrigerated for up to three days or frozen for up to a month. Just bring it to room temperature and roll it out as usual before cutting and baking.

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

No worries! You can use any fall-themed cookie cutter or even a simple circle cutter—the faces are the key to the jack-o-lantern look, so you can cut small face shapes on top cookies regardless.

How can I make these cookies vegan?

To veganize this recipe, substitute butter with a vegan butter alternative, use flax eggs instead of regular eggs, and choose dairy-free milk chocolate. The flavor and texture will still be deliciously festive!

Final Thoughts

Trying your hand at Milk Chocolate Stuffed Jack-O-Lantern Cookies is like capturing the heart of autumn in a single, delicious bite. These cookies are a joyful way to celebrate the season, whether you’re baking with family or sharing them at a cozy get-together. I encourage you to dive into this recipe wholeheartedly—you’ll create not just wonderful cookies but lasting memories filled with warmth, laughter, and that unbeatable chocolatey goodness.

Milk Chocolate Stuffed Jack-O-Lantern Cookies Recipe

★★★★★

4.8 from 12 reviews

Author: Hugo
Total Time: 1 hour 10 minutes
Yield: About 24 stuffed jack-o-lantern cookies 1x
Diet: Vegetarian

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Description

Delightfully festive and perfect for Halloween, these Milk Chocolate Stuffed Jack-O-Lantern Cookies combine spiced sugar cookie dough with a creamy milk chocolate center. Carved with charming jack-o-lantern faces, they offer a fun, seasonal treat that’s both visually appealing and deliciously satisfying.

Instructions

Prepare the Dough: In a large mixing bowl, cream together the softened butter and light brown sugar until light and fluffy, about 3-5 minutes. Add in the vanilla extract and then mix in the eggs one at a time until fully combined. Gradually incorporate the flour, baking soda, cinnamon, ginger, nutmeg, and salt until the dough forms a cohesive ball. Add a little extra flour if dough is too sticky.
Roll and Cut the Cookies: Flour your work surface generously. Divide the dough into two halves and shape each into a disk. Roll out each disk to about 1/4-inch thickness. Use a pumpkin-shaped cookie cutter to cut out cookies. For half, carve jack-o-lantern faces with a knife or smaller cutters. Place the cookies on a parchment-lined baking sheet and chill in the freezer for 15-20 minutes to firm.
Bake the Cookies: Preheat the oven to 350°F (175°C). Arrange chilled cookies on the middle rack of the oven and bake for 8-12 minutes until edges are lightly golden. Let cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.
Prepare the Cinnamon Sugar Topping: Melt 2 tablespoons of butter in a small pan over medium heat, cooking until it becomes a light golden brown with a toasted aroma (about 2-3 minutes). Allow to cool slightly. Brush this browned butter over the jack-o-lantern face cookies and sprinkle with cinnamon sugar for extra flavor.
Assemble the Cookies: Spread the melted milk chocolate generously on the flat, non-face cookies. Place the jack-o-lantern face cookies on top, pressing gently to adhere. Allow the chocolate to set completely before serving for the perfect stuffed cookie experience.

Notes

Chilling the dough helps prevent the cookies from spreading too much during baking, preserving the jack-o-lantern shapes.
Use high-quality milk chocolate for a richer filling that sets nicely between the cookie layers.
The browned butter cinnamon sugar topping adds a warm, nutty flavor that complements the spices in the dough.
Store the assembled cookies in an airtight container at room temperature for up to 3 days.
For a dairy-free option, substitute butter and milk chocolate with vegan alternatives.

Prep Time: 25 minutes
Cook Time: 12 minutes
Category: Dessert, Cookies
Method: Baking
Cuisine: American