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Celebrate Halloween with Milk Chocolate Stuffed Jack-O’-Lantern Cookies, soft treats filled with creamy chocolate. These Festive Halloween Cookies are perfect for spooky parties or cozy baking. Enjoy this simple recipe for a chocolate-filled pumpkin cookie that delights all!

Why You’ll Love Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Chewy Bliss: Milk Chocolate Stuffed Jack-O’-Lantern Cookies shine in this simple recipe.
Rich Filling: Creamy chocolate in these festive Halloween cookies.
Party-Ready: Ideal for events with this spooky dessert.
Fun to Make: Kid-friendly for this chocolate-filled pumpkin cookie.
Make-Ahead: Perfect for prepping this festive Halloween cookie.

Ingredients for Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Here’s what you’ll need for this spooky dessert (makes ~16 cookies):

2 ½ cups (310 g) all-purpose flour
½ tsp baking powder
½ tsp salt
1 cup (225 g) unsalted butter, softened
1 cup (200 g) packed brown sugar
½ cup (100 g) granulated sugar
1 large egg
1 tsp vanilla extract
8 oz (225 g) milk chocolate (bars or chips), melted or chopped
Orange food coloring gel (optional)
Optional: Black gel icing or melted dark chocolate, sprinkles

Equipment

Large mixing bowls
Electric or stand mixer
Measuring cups and spoons
Rolling pin
Pumpkin-shaped cookie cutter
Small paring knife
Baking sheets with parchment paper
Cooling racks

Ingredient Tips

Chocolate: Quality milk chocolate for this chocolate-filled pumpkin cookie.
Brown Sugar: Adds depth to these festive Halloween cookies.
Flour: Ensures structure for this simple recipe.
Food Coloring: Orange gel for this spooky dessert’s charm.
Icing: Black gel for this festive Halloween cookie’s faces.

Directions

Let’s create this delightful spooky dessert!

Make Cookie Dough

I whisk 2 ½ cups flour, ½ tsp baking powder, and ½ tsp salt in a bowl. In another, I beat 1 cup butter, 1 cup brown sugar, and ½ cup granulated sugar until fluffy, add 1 egg and 1 tsp vanilla, then mix in dry ingredients. I optionally tint half the dough orange, wrap, and chill 30 minutes for this simple recipe.

Cut Out Cookies

I preheat the oven to 350°F (175°C). On a floured surface, I roll dough to ¼-inch thick, cut out ~32 pumpkin shapes (16 pairs), and carve Jack-O’-Lantern faces on half with a knife for these festive Halloween cookies.

Stuff and Bake

I spoon 8 oz melted milk chocolate onto whole cookies, top with carved cookies, seal edges, and bake on parchment-lined sheets for 10–12 minutes until golden for this chocolate-filled pumpkin cookie.

Decorate and Serve

I cool cookies on racks, optionally decorate with black gel icing for faces or sprinkles, and serve for this Milk Chocolate Stuffed Jack-O’-Lantern Cookies.

Nutrition

Prep Time: 20 minutes
Chill Time: 30 minutes
Cook Time: 10–12 minutes
Total Time: ~1 hour
Servings: ~16 cookies
Calories: ~250 kcal per cookie
Macros per Cookie: 30g carbs, 3g protein, 12g fat

Variations for Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Try these twists on this spooky dessert:

Candy-Filled: Use peanut butter cups for this chocolate-filled pumpkin cookie.
Mini Cookies: Make bite-sized festive Halloween cookies.
Gluten-Free: Use gluten-free flour for this simple recipe.
Vegan: Swap butter for margarine in this spooky dessert.
Dark Chocolate: Use dark chocolate for this festive Halloween cookie.

Serving Ideas:

Pair with Food and Tips’ pumpkin soup for a cozy chocolate-filled pumpkin cookie meal.
Serve with Food and Tips’ cider for a festive Halloween cookie vibe.
Enjoy with Food and Tips’ beet salad for a spooky dessert spread.

Storage

I store these chocolate-filled pumpkin cookies in an airtight container at room temperature for 3 days or refrigerate for 1 week. Freeze for 1 month and thaw before serving this simple recipe.

Serving Tips

Presentation: Serve Milk Chocolate Stuffed Jack-O’-Lantern Cookies on a dark platter for a festive Halloween cookie.
Garnish: Add edible glitter for this spooky dessert’s charm.
Pairing: Enjoy with Food and Tips’ cocoa for a chocolate-filled pumpkin cookie treat.
Portion Size: 1–2 cookies per person for a satisfying serving.
Occasions: Perfect for Halloween parties, bake sales, or cozy nights.

FAQs About Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Here are answers to common questions about this festive Halloween cookie:

Can I make dough ahead?
Yes, chill up to 2 days for this chocolate-filled pumpkin cookie.

Can I use other chocolate?
Dark or white chocolate works for this spooky dessert.

Can I freeze cookies?
Yes, freeze for 1 month for this festive Halloween cookie.

No pumpkin cutter?
Use a round cutter and shape stems for this simple recipe.

How to prevent leaks?
Use minimal filling for this chocolate-filled pumpkin cookie.

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Conclusion

Milk Chocolate Stuffed Jack-O’-Lantern Cookies are a whimsical, chocolatey treat for Halloween. This simple recipe delivers a delightful festive Halloween cookie perfect for parties or cozy nights. Enjoy these chocolate-filled pumpkin cookies that bring spooky fun!

Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Milk Chocolate Stuffed Jack-O’-Lantern Cookies are a whimsical, chocolatey treat for Halloween. This simple recipe delivers a delightful festive Halloween cookie perfect for parties or cozy nights.

Print Recipe Pin Recipe

Prep Time 20

Cook Time 10

Total Time 1

Course cookies

Cuisine American

Servings 16 cookies

Calories 250 kcal

Ingredients

2 ½ cups 310 g all-purpose flour
½ tsp baking powder
½ tsp salt
1 cup 225 g unsalted butter, softened
1 cup 200 g packed brown sugar
½ cup 100 g granulated sugar
1 large egg
1 tsp vanilla extract
8 oz 225 g milk chocolate (bars or chips), melted or chopped
Orange food coloring gel optional
Optional: Black gel icing or melted dark chocolate sprinkles