why make this recipe
Milk Chocolate Stuffed Jack-O’-Lantern Cookies are the perfect treat for Halloween or any fun fall gathering. These cookies combine the warmth and spice of autumn with a rich milk chocolate surprise inside. They’re not just delicious, but they also bring a playful spirit to your dessert table. Kids and adults alike will love the cute pumpkin designs and the gooey filling. Baking these cookies can be a great family activity, making them a wonderful way to bond and create delicious memories together.
how to make Milk Chocolate Stuffed Jack-O’-Lantern Cookies
Ingredients:
- 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
- 12 ounces milk chocolate, melted
- 2 tablespoons salted butter
- 3 tablespoons cinnamon sugar
Directions:
In a large mixing bowl, cream together the butter, sugar, and vanilla until light and fluffy, which takes about 3-5 minutes. Add the eggs one at a time, mixing until everything is well combined. Then, add the flour, baking soda, cinnamon, ginger, nutmeg, and salt. Beat the mixture until combined, forming a dough ball.
Generously flour your work surface. Divide the dough in half and flatten each half into a disk. Roll out the dough to 1/4 inch thickness. Use enough flour to prevent sticking. Cut out pumpkin shapes using a cookie cutter. Carefully transfer the cookies to a parchment-lined baking sheet. Use a pairing knife or cookie cutter to cut out eyes and a mouth in half of the cookies. Cover the baking sheet and freeze for about 15-20 minutes until firm. Roll out leftover scraps and repeat with the remaining dough.
Preheat your oven to 350 degrees. Bake the cookies on the middle rack for about 8-12 minutes, or until they are lightly golden brown. Make sure not to overbake. Let the cookies cool on the baking sheet for five minutes before transferring them to a wire cooling rack to cool completely.
In a medium pot, add the butter and allow it to brown slightly until it smells toasted, which takes about 2-3 minutes. Stir often. Remove from heat and let cool for 5 minutes. Brush the brown butter over the top half of the cookies, then sprinkle with cinnamon sugar.
To assemble the cookies, spread melted milk chocolate on the bottom half of the cookies without faces. Place the pumpkin-faced cookies on top, pressing gently to make them stick. You can serve them right away or let the chocolate firm up and store them in an airtight container for up to three days.
how to serve Milk Chocolate Stuffed Jack-O’-Lantern Cookies
These cookies are best served fresh, but they can also be enjoyed later once the chocolate has set. They make for great party favors, treats for trick-or-treaters, or just a sweet snack during family movie night. Adding a glass of milk or a warm cup of cider can make the experience even better.
how to store Milk Chocolate Stuffed Jack-O’-Lantern Cookies
To keep the cookies fresh, store them in an airtight container at room temperature. They will stay good for up to three days. If you want to keep them longer, you can freeze them. Just make sure to wrap them well to prevent freezer burn.
tips to make Milk Chocolate Stuffed Jack-O’-Lantern Cookies
- Make sure your butter is softened for the best texture. Leave it at room temperature for about an hour before starting.
- Don’t overwork the dough once you add the flour; mixing too much can make the cookies tough.
- Use a variety of pumpkin cookie cutters for fun shapes and sizes.
- If your dough is sticky, refrigerate it for a bit before rolling it out.
- Experiment with different chocolate types or add some orange food coloring to the chocolate for a spooky twist.
variation (if any)
You can switch up the filling by using white chocolate, dark chocolate, or even caramel instead of milk chocolate. Another fun variation is to add mini chocolate chips or candy corn inside the cookies for an extra sweet surprise.
FAQs
1. Can I use unsalted butter instead of salted butter?
Yes, you can use unsalted butter. Just add a pinch of salt to the dough for flavor.
2. How do I prevent the cookies from spreading too much while baking?
Chilling the dough before baking and ensuring your oven is accurately preheated can help maintain the cookies’ shape.
3. Can I freeze the dough before baking?
Absolutely! You can freeze the cookie dough for up to two months. Just roll it into disks or cut shapes and wrap it tightly before freezing. Thaw in the fridge before baking.

Milk Chocolate Stuffed Jack-O'-Lantern Cookies
Ingredients
Method
- In a large mixing bowl, cream together the butter, sugar, and vanilla until light and fluffy, about 3-5 minutes.
- Add the eggs one at a time, mixing until well combined.
- Add the flour, baking soda, cinnamon, ginger, nutmeg, and salt, then beat until combined to form a dough ball.
- Generously flour your work surface. Divide the dough in half and flatten into disks, then roll out to 1/4 inch thickness.
- Cut out pumpkin shapes using a cookie cutter and transfer to a parchment-lined baking sheet.
- Use a pairing knife to cut out eyes and a mouth in half of the cookies. Cover and freeze for 15-20 minutes until firm.
- Roll out leftover scraps and repeat with the remaining dough.
- Preheat the oven to 350 degrees. Bake the cookies on the middle rack for about 8-12 minutes until lightly golden brown.
- Let the cookies cool on the baking sheet for 5 minutes, then transfer them to a wire cooling rack to cool completely.
- In a medium pot, brown the butter slightly, stirring often for 2-3 minutes. Let cool for 5 minutes.
- Brush the brown butter over the top of the cookies without faces and sprinkle with cinnamon sugar.
- Spread melted milk chocolate on the bottom halves of the cookies without faces, then press the pumpkin-faced cookies on top.
- Serve right away or let the chocolate firm up before storing in an airtight container for up to three days.
