The Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe is a festive, comforting treat that’s perfect for cozy autumn days. These charming cookies combine a soft, buttery spiced cookie exterior with a luscious milk chocolate center, giving you the best of both worlds in every bite. Whether you’re baking for a Halloween party, a family gathering, or simply to enjoy a delicious homemade snack, this recipe brings warmth, sweetness, and a little bit of seasonal magic all wrapped up in a delightful pumpkin shape.

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

Ingredients You’ll Need

Gathering the right ingredients for the Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe is straightforward, and each one plays a key role in creating those perfect autumnal flavors and textures. From the rich butter that enriches the dough to the warm spices that make the cookies taste like fall in every bite, this ingredient list is simple but essential.

  • Unsalted butter (1 ½ cups or 3 sticks): Provides the rich, creamy base for tender cookies.
  • Brown sugar (1 cup, packed): Adds moisture and a deep, caramel-like sweetness.
  • Granulated sugar (½ cup): Balances sweetness while helping with texture.
  • Large eggs (2): Bind ingredients and contribute to cookie structure.
  • Vanilla extract (1 tablespoon): Enhances overall flavor with a warm, aromatic touch.
  • All-purpose flour (3 ¾ cups): Forms the sturdy yet tender part of the cookie dough.
  • Baking soda (1 teaspoon): Leavens the dough for a light, soft bite.
  • Ground cinnamon (1 teaspoon): Brings classic fall warmth and flavor.
  • Ground ginger (½ teaspoon): Adds a subtle spicy kick.
  • Ground nutmeg (¼ teaspoon): Delivers a hint of aromatic earthiness.
  • Salt (½ teaspoon): Balances sweetness and amplifies spices.
  • Milk chocolate (12 oz, chopped or bars): Stuffed inside each cookie for gooey, rich goodness.
  • Cinnamon sugar (for dusting): Adds a sweet, crunchy finish on top.

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

Step 1: Cream the Butter and Sugars

Start by beating the room temperature butter with both brown and granulated sugars until the mixture becomes light and fluffy. This step is vital because it incorporates air, helping to create soft and tender cookies. Once that’s done, add the eggs one at a time, ensuring each is fully mixed in before the next, then stir in the vanilla extract for that lovely fragrant boost.

Step 2: Combine Dry Ingredients and Form Dough

In a separate bowl, whisk together the flour, baking soda, cinnamon, ginger, nutmeg, and salt. This careful mix of spices will infuse the cookies with classic fall flavors. Gradually add the dry mixture to your wet batter, mixing steadily until a soft dough forms. Then, split the dough into two portions, wrap them tightly in plastic, and chill for at least 30 minutes to make rolling easier and to preserve the butter’s texture.

Step 3: Cut Out the Cookie Shapes

Once chilled, preheat your oven to 350°F (175°C). Lightly flour your workspace and roll out the dough to about ¼-inch thickness. Use a pumpkin-shaped cookie cutter to cut out as many pieces as possible. For half of those pumpkin pieces, use a small sharp knife or a specialized cutter to carve out Jack-O’-Lantern faces — these will become the cookie tops that reveal the melted chocolate inside.

Step 4: Assemble the Cookies with Milk Chocolate Filling

Place the plain pumpkin dough cutouts on a parchment-lined baking sheet. Nestle a piece of milk chocolate right in the center of each cookie — this chocolate is the heart of the Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe. Top with a Jack-O’-Lantern cutout and gently press the edges to seal the chocolate inside, creating that magical chocolate surprise.

Step 5: Bake and Finish with Cinnamon Sugar

Bake your assembled cookies for 10 to 12 minutes or until they start to turn a gentle golden color. As soon as they come out of the oven, dust the tops with cinnamon sugar for a sweet, sparkly finish that perfectly complements the warm spices. Let the cookies cool on the baking sheet for 5 minutes before transferring them to a rack, so they firm up just right without losing any of that melty goodness inside.

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

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

Garnishes

For an extra touch of seasonal charm, try sprinkling a bit more cinnamon sugar or even a light dusting of powdered sugar before serving. A few edible autumn leaves or a small candy pumpkin on the side can make the presentation really festive and inviting. These little details make your cookies feel like a delightful gift from the kitchen.

Side Dishes

These cookies pair beautifully with a warm cup of apple cider, a cozy chai latte, or even a cold glass of milk — each drinks helps balance the richness of the chocolate and spices. You could also offer roasted pumpkin seeds or spiced nuts on the side to keep the fall theme running strong and add some crunchy variety for your guests.

Creative Ways to Present

Whether you arrange these cookies on a rustic wooden platter or stack them in a clear jar tied with an orange ribbon, presentation sets the mood. For parties, serve them alongside little bowls of melted chocolate and cinnamon sugar for dipping. Wrapping individual cookies in parchment paper tied with twine makes them perfect for gift-giving or party favors — and everyone will be impressed by your crafty, delicious effort.

Make Ahead and Storage

Storing Leftovers

If you have any leftover Milk Chocolate Stuffed Jack-O’-Lantern Cookies, store them in an airtight container at room temperature for up to 3 days. The cookies stay soft and the chocolate inside keeps its gooey texture, making them just as enjoyable the next day.

Freezing

You can freeze the unbaked cookie dough or the fully baked cookies. For dough, wrap tightly in plastic wrap and freeze for up to 3 months — thaw overnight in the fridge before baking as usual. For baked cookies, freeze in a sealed container with parchment between layers to avoid sticking, and enjoy them anytime you need a little autumn delight.

Reheating

To bring that stuffed chocolate back to melty perfection, warm the cookies in a microwave for about 10-15 seconds or in a preheated 300°F oven for 3-5 minutes. This gentle reheating will refresh the flavors and textures without drying them out.

FAQs

Can I use dark chocolate instead of milk chocolate?

Absolutely! While this recipe is designed for milk chocolate’s creamy sweetness, switching to dark chocolate will add a richer, slightly bitter contrast that pairs wonderfully with the spiced dough.

Do I have to chill the dough before baking?

Chilling the dough is important because it firms up the butter, prevents spreading, and makes it easier to roll and cut the pumpkin shapes precisely. Skipping this step might affect the cookie’s texture and shape.

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

If you don’t have a pumpkin-shaped cutter, you can use any round or oval cutter and draw Jack-O’-Lantern faces with a knife on half of the cookies. Freehand or stencil, the character of the cookies still shines through with a little creativity.

Can I make these cookies gluten-free?

To make the Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe gluten-free, substitute the all-purpose flour with a gluten-free baking blend that measures cup-for-cup. Keep an eye on the dough’s texture—it might require a little adjustment in chilling time or moisture.

How long will these cookies stay fresh?

Stored in an airtight container at room temperature, these cookies stay fresh for about 3 days. Beyond that, it’s best to store them in the fridge or freezer to maintain their texture and keep the chocolate fresh.

Final Thoughts

I can’t recommend the Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe enough for anyone looking to add a bit of sweetness and warmth to their fall baking. These cookies are joyful to make, even more delightful to share, and a guaranteed crowd-pleaser with their rich chocolate centers and fun seasonal shapes. Give this recipe a try and watch your kitchen fill with the cozy scents of autumn—and those big smiles from anyone lucky enough to savor these treats.

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Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.2 from 89 reviews
  • Author: Diane
  • Prep Time: 30 minutes
  • Cook Time: 10-12 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 and delicious treats perfect for Halloween. Soft spiced sugar cookies are filled with creamy milk chocolate, topped with cute Jack-O’-Lantern faces, and dusted with cinnamon sugar for a flavorful and fun dessert.


Ingredients

Scale

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

  1. Prepare the dough: In a large bowl, beat the butter, brown sugar, and granulated sugar together until light and fluffy, about 2-3 minutes. Add the eggs one at a time, then the vanilla extract, mixing well after each addition.
  2. Mix dry ingredients and combine: In a separate bowl, whisk together the flour, baking soda, cinnamon, ginger, nutmeg, and salt. Gradually add the dry ingredients to the wet mixture, stirring until a dough forms. Divide dough in half, wrap in plastic, and refrigerate for at least 30 minutes until firm.
  3. Roll and cut dough: Preheat oven to 350°F (175°C). On a lightly floured surface, roll out chilled dough to about ¼-inch thickness. Use a pumpkin-shaped cookie cutter to cut cookies. Cut faces into half of the pumpkins using a sharp knife or small cookie cutter for Jack-O’-Lantern designs.
  4. Assemble cookies: Place uncut pumpkin cookies on a parchment-lined baking sheet. Center a piece of milk chocolate on each. Top with the Jack-O’-Lantern cut-out cookies and press edges gently to seal the filling inside.
  5. Bake: Bake cookies for 10-12 minutes or until lightly golden around the edges. Remove from oven, dust with cinnamon sugar while warm, and cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Notes

  • Chilling the dough is crucial for easy rolling and clean cookie shapes.
  • You can substitute semi-sweet or dark chocolate if preferred.
  • Ensure edges are sealed well to prevent chocolate from oozing out during baking.
  • Store cookies in an airtight container at room temperature for up to 5 days.
  • For a festive touch, use colored sugar or sprinkles instead of cinnamon sugar.

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