Name: Milk Chocolate Stuffed Jack-O'-Lantern Cookies
Prep time: 30 min
Cook time: 12 min
Total time: 42 min
Cuisine: American
Ingredients: 1 1/2 cups salted butter, softened; 1 1/4 cups light brown sugar, packed; 1 tablespoon pure vanilla extract; 2 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 ounces milk chocolate, melted; 2 tablespoons salted butter; 3 tablespoons cinnamon sugar

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If you’re looking for a fun and delicious treat to celebrate Halloween or just to brighten up a regular day, these Milk Chocolate Stuffed Jack-O’-Lantern Cookies are perfect! Imagine biting into a soft, spiced brown sugar cookie only to find creamy milk chocolate hidden inside. It’s like a little surprise in every bite, making them a favorite not just for kids but for anyone who loves a good cookie. Whether you’re hosting a Halloween party, enjoying a cozy fall evening with family, or just treating yourself, these cookies will surely bring smiles all around.

I love how versatile this recipe is. You can whip it up on busy weeknights or make them ahead for gatherings. Plus, they look adorable with their pumpkin faces, adding a festive touch to any occasion!

Why You’ll Love This Recipe

Easy to Make: With simple steps and familiar ingredients, making these cookies is a breeze!
Family-Friendly Fun: Kids will love helping to cut out the shapes and decorate with chocolate.
Perfect for Any Occasion: Whether it’s Halloween or Thanksgiving, these cookies fit right in.
Delicious Flavor: The combination of spices and sweet milk chocolate creates an unforgettable taste.
Make-Ahead Convenience: Bake them ahead of time and store for quick treats throughout the week.

Ingredients You’ll Need

To make these delightful Milk Chocolate Stuffed Jack-O’-Lantern Cookies, you’ll need some simple and wholesome ingredients that you likely already have in your pantry. Here’s what you’ll need:

For the Cookies

3 sticks (1 1/2 cups) salted butter, softened
1 1/4 cups light brown sugar, packed
1 tablespoon pure vanilla extract
2 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

For the Filling and Topping

12 ounces milk chocolate, melted
2 tablespoons salted butter
3 tablespoons cinnamon sugar

Variations

This recipe is wonderfully flexible! You can easily tweak it to suit your tastes or dietary needs. Here are some fun ideas:

Try Dark Chocolate: If you’re a fan of rich flavors, swap out the milk chocolate for dark chocolate.
Add Nuts: Sprinkle in some chopped nuts like pecans or walnuts for added crunch and flavor.
Experiment with Spices: Feel free to add other spices like cloves or allspice for an extra kick.
Make Them Gluten-Free: Use a gluten-free flour blend instead of all-purpose flour for gluten-free cookies.

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

Step 1: Cream Together the Butter and Sugar

In a large mixing bowl, cream together the softened butter, light brown sugar, and vanilla extract until light and fluffy. This usually takes about 3-5 minutes. This step is crucial because it incorporates air into your mixture, which helps make the cookies nice and soft!

Step 2: Combine Wet Ingredients and Dry Ingredients

Add the eggs one at a time, mixing well after each addition. Then gradually add in the flour, baking soda, cinnamon, ginger, nutmeg, and salt. Mix until everything is combined and forms a cohesive dough. This is where the flavors start to come together!

Step 3: Roll Out the Dough

Generously flour your work surface before dividing your dough in half. Flatten each half into disks and roll out to about 1/4 inch thickness. Use enough flour here—no one likes sticky dough! Cut out cookies using a pumpkin-shaped cutter. Make sure you also cut out eyes and mouths on half of them so they can be assembled later.

Step 4: Chill Before Baking

Carefully transfer your cookie shapes to a parchment-lined baking sheet. Cover with plastic wrap and place in the freezer for about 15-20 minutes until firm. Chilling prevents spreading while baking so you get those adorable pumpkin shapes.

Step 5: Bake Until Golden Brown

Preheat your oven to 350 degrees Fahrenheit while you wait. Bake your cookies on the middle rack for about 8-12 minutes until they are just lightly golden brown around the edges. Be careful not to overbake; we want soft cookies! Let them cool on the baking sheet for five minutes before transferring them to a wire cooling rack.

Step 6: Add Cinnamon Sugar Topping

While your cookies cool, melt additional butter in a medium pot over low heat until it slightly browns and smells toasted—about 2-3 minutes. Brush this golden butter over the tops of half of your cooled cookies before sprinkling generously with cinnamon sugar.

Step 7: Assemble Your Cookie Sandwiches

Spread melted milk chocolate over the flat side of each un-faced cookie. Place one of your decorated pumpkin-faced cookies on top of each one and gently press down so they stick together nicely. You can enjoy these right away or let them sit so that chocolate firms up before storing them in an airtight container.

Now you’re ready to share (or keep) these delightful Milk Chocolate Stuffed Jack-O’-Lantern Cookies! Enjoy every bite!

Pro Tips for Making Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Baking is an adventure, and with these handy tips, you can make your cookie experience even sweeter!

Use room temperature ingredients: This allows for better mixing, creating a smoother dough that results in perfectly soft cookies.
Chill the dough: If the dough feels too soft to work with, chilling it for an additional 10-15 minutes can make rolling out and cutting shapes much easier.
Don’t overbake: Keep an eye on your cookies while they bake. They should be just lightly golden brown around the edges; this ensures they remain soft and chewy inside.
Experiment with chocolate types: While milk chocolate is delightful, consider trying dark chocolate or even white chocolate for a different flavor twist!
Add fun decorations: Use colorful sprinkles or edible glitter on top of the cookies after brushing them with butter for a festive look that’s sure to impress.

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

These cookies are not only delicious but also visually appealing, making them perfect for any occasion. Whether it’s a Halloween party or a cozy family gathering, here are some fun ways to serve them!

Garnishes

Chocolate drizzles: A drizzle of melted chocolate on top adds an elegant touch and extra sweetness.
Whipped cream: A dollop of whipped cream beside the cookies can provide a lovely contrast in texture and flavor.

Side Dishes

Pumpkin spice latte: The warm spices in this classic drink complement the flavors of the cookies perfectly, creating a cozy pairing.
Apple cider: Serve warm apple cider alongside your cookies for a comforting fall treat that enhances the seasonal experience.
Cheese platter: A selection of mild cheeses can balance out the sweetness of the cookies while providing a savory element to your dessert spread.
Vanilla ice cream: Pairing these cookies with a scoop of vanilla ice cream creates an irresistible dessert combo that everyone will love!

Now that you’re armed with all these tips and serving ideas, you’re ready to whip up some delightful Milk Chocolate Stuffed Jack-O’-Lantern Cookies that will steal the show at any gathering! Happy baking!

Make Ahead and Storage

These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are not just delicious; they’re also perfect for meal prep! You can make them in advance and enjoy the delightful flavors whenever you want.

Storing Leftovers

Store any leftover cookies in an airtight container at room temperature.
They will stay fresh for up to 3 days, but trust me, they won’t last that long!

Freezing

To freeze, place the assembled cookies in a single layer on a baking sheet and freeze until solid.
Once frozen, transfer them to a freezer-safe bag or container. They can be stored for up to 2 months.
For best results, freeze before adding any toppings like cinnamon sugar.

Reheating

To reheat frozen cookies, allow them to thaw at room temperature for about 30 minutes.
Warm them in a preheated oven at 350°F (175°C) for about 5 minutes to restore their soft texture.

FAQs

Got questions? No problem! Here are some common inquiries about these charming cookies.

Can I use dark chocolate instead of milk chocolate for the Jack-O’-Lantern Cookies?

Absolutely! While this recipe calls for milk chocolate, dark chocolate can add a deliciously rich flavor that pairs well with the spiced brown sugar cookies.

How do I store Milk Chocolate Stuffed Jack-O’-Lantern Cookies?

To store your Milk Chocolate Stuffed Jack-O’-Lantern Cookies, keep them in an airtight container at room temperature for up to 3 days. Enjoy the sweetness while it lasts!

Can I make the cookie dough ahead of time?

Yes! You can prepare the dough ahead of time and refrigerate it. Just wrap it tightly in plastic wrap and store it in the fridge for up to 3 days before rolling out and baking.

What if I don’t have pumpkin cookie cutters?

No worries! You can use any shape cookie cutter you have on hand. Just remember that they won’t have that classic jack-o’-lantern look but will still taste fantastic!

Are these cookies suitable for kids?

Definitely! These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are kid-friendly and perfect for Halloween parties or family gatherings. Just make sure to supervise younger children when using kitchen tools.

Final Thoughts

I hope you find as much joy in making these Milk Chocolate Stuffed Jack-O’-Lantern Cookies as I do! They’re not only a fun treat to prepare but also a delightful dessert that brings smiles all around. Perfect for sharing with friends and family during Halloween or Thanksgiving gatherings—or anytime you need a bit of sweetness in your life. Happy baking, and don’t forget to share your cookie creations with me!

Milk Chocolate Stuffed Jack-O’-Lantern Cookies

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Author: Madison
Prep Time: 30 minutes
Cook Time: 12 minutes
Total Time: 42 minutes
Yield: Approximately 24 cookies 1x
Category: Dessert
Method: Baking
Cuisine: American

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Description

Celebrate fall with these delightful Milk Chocolate Stuffed Jack-O’-Lantern Cookies, a perfect treat for Halloween or any cozy gathering. Each cookie features a soft, spiced brown sugar base that hides a luscious milk chocolate filling, ensuring a delicious surprise in every bite. They’re not only fun to make but also visually appealing with their cute pumpkin faces, making them an instant hit among kids and adults alike. With their easy preparation and versatile options, these cookies are ideal for both busy weeknights and festive occasions. Get ready to spread joy with each sweet creation!

Ingredients

Scale

1 1/2 cups salted butter, softened
1 1/4 cups light brown sugar, packed
1 tablespoon pure vanilla extract
2 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 ounces milk chocolate, melted
2 tablespoons salted butter
3 tablespoons cinnamon sugar

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Instructions

In a large bowl, cream together the butter and brown sugar until fluffy. Mix in the vanilla extract and eggs one at a time.
Gradually add flour, baking soda, spices, and salt; mix until combined to form dough.
Roll out the dough to about 1/4 inch thick and cut into pumpkin shapes (with eyes and mouths).
Chill the shapes in the freezer for 15–20 minutes before baking at 350°F for 8–12 minutes until lightly golden.
Cool slightly, brush melted butter on half of the cookies, sprinkle with cinnamon sugar, then sandwich with melted chocolate.