Irresistible Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Name: Milk Chocolate Stuffed Jack-O'-Lantern Cookies
Prep time: 15 min
Cook time: 12 min
Total time: 27 min
Cuisine: American
Ingredients: 2 1/4 cups all-purpose flour; 1 cup granulated sugar; 1/2 cup brown sugar, packed; 1 tsp baking soda; 1 cup unsalted butter, softened; 2 large eggs (room temperature); 2 tsp pumpkin spice; 1 cup milk chocolate chips; 1 tsp vanilla extract

Published: September 16, 2025

by Amelia

Why You'll Love This Recipe

The Milk Chocolate Stuffed Jack-O’-Lantern Cookies are incredibly easy to prepare, perfect for novice bakers or seasoned pros alike
Their chocolatey flavor combined with festive pumpkin spice makes them irresistibly delicious
These cookies are visually stunning, bringing a fun Halloween vibe to any gathering
Their versatility means you can enjoy them any time of the year, not just during spooky season

Every time I bake these cookies, my kids gather around like moths to a flame, eagerly waiting for the warm treats to come out of the oven.

Essential Ingredients

Here’s what you’ll need to make this delicious dish:

All-Purpose Flour: Use fresh flour for the best texture. Sift it for lighter cookies if desired.
Granulated Sugar: This adds sweetness and helps create those beautiful golden edges.
Brown Sugar: The molasses in brown sugar gives these cookies that rich color and depth.
Baking Soda: This is essential for making your cookies rise beautifully. For more inspiration, check out this Thick and Chewy Caramel Coconut Cookies recipe.
Butter: Use unsalted butter for better control over salt levels in your baking.
Eggs: They add richness and moisture; room temperature eggs work best!
Pumpkin Spice: The star ingredient for that seasonal warmth and flavor burst.
Milk Chocolate Chips: Choose good quality chocolate chips; they’re the gooey surprise inside every cookie.
Vanilla Extract: Pure vanilla extract enhances all those lovely flavors harmoniously.

The full ingredients list, including measurements, is provided in the recipe card directly below.

Milk Chocolate Stuffed Jack-O'-Lantern Cookies

Let’s Make it Together

Preheat Your Oven: Start by preheating your oven to 350°F (175°C). This ensures even baking right from the start.

Create Your Cookie Dough Base: In a large bowl, cream together softened butter with granulated sugar and brown sugar until fluffy and light. The mixture should look pale and inviting.

Add Eggs and Vanilla: Mix in one egg at a time along with vanilla extract. Beat until smooth; this adds moisture and flavor throughout your dough.

Sift in Dry Ingredients: Gradually add in flour, baking soda, pumpkin spice, and salt. Spooky Ghost Pumpkin Cookies Stir gently until just combined; don’t overmix or you’ll have tough cookies!

Fold in Chocolate Chips: Carefully fold in the milk chocolate chips until evenly distributed throughout your dough. Feel free to sneak a few for yourself!

Scoop & Bake!: Using a cookie scoop or tablespoon, drop rounded mounds of dough onto parchment-lined baking sheets about two inches apart. Bake for 10-12 minutes until edges are lightly golden but centers remain soft.

Enjoy the delightful aroma wafting through your kitchen as these magical treats bake! Allow them to cool on the tray for five minutes before transferring them to wire racks for complete cooling.

These Milk Chocolate Stuffed Jack-O’-Lantern Cookies aren’t just about taste—they’re about creating memories around the kitchen table with laughter and love. So go ahead—dive into this festive treat that will surely enchant everyone who bites into its delightful charm! For more inspiration, check out this Irresistible Double Chocolate Cookies recipe.

You Must Know

Milk chocolate stuffed Jack-O’-Lantern cookies bring a fun twist to your Halloween treats
The gooey chocolate center and vibrant orange color will wow your guests
Plus, they are easy to make, leaving you more time for spooky decorations!

Perfecting the Cooking Process

Start by chilling the dough before baking to avoid spreading. Shape your cookies, then refrigerate them while preheating the oven. This ensures that they hold their shape during baking, resulting in perfectly plump Jack-O’-Lantern cookies.

Add Your Touch

Feel free to swap milk chocolate with dark or white chocolate for a different flavor profile. You can also add orange zest or spices like cinnamon for an extra kick. Get creative with your cookie designs; the spookier, the better!

Storing & Reheating

Store these cookies in an airtight container at room temperature for up to five days. If you need to reheat them, pop them in the microwave for about 10 seconds to revive that melty chocolate goodness.

Chef's Helpful Tips

For fluffy cookies, don’t overmix the dough; mix just until combined
Use a cookie scoop for uniform sizes, ensuring even baking
Lastly, let them cool slightly before indulging to avoid burning your tongue on that delicious melted chocolate

There’s nothing quite like watching friends’ faces light up when they take a bite of these delightful cookies. I once brought a batch to a Halloween party and they vanished faster than you could say “Boo!”