A fun twist on Pumpkin Sugar Cookies, these Jack O’Lantern cookies taste like a homemade Milano cookie – but with a fun Halloween twist!
Jack O’Lantern Cookies Recipe
Milanos are one of my favorite cookies when I’m craving chocolate.
They are that perfect combination of melt-in-your-mouth sugar cookie, rich chocolate ganache, and I find even having a single one is super satisfying.
Now these aren’t exactly like a Milano because the cookies they use have a very “wet” batter which cannot be cut into shapes, and I really wanted to make my homemade Milanos into Jack O’Lantern shapes, but I think my homemade sugar cookie recipe works perfectly with the traditional bittersweet chocolate ganache (which tastes exactly like the Milano version).
You can skip a few steps and use premade sugar cookie dough, but I personally don’t find that it tastes that great. Sugar cookie dough is super simple to make and once you taste the difference in these homemade cookies, you won’t ever give the store-bought dough a second glance.
These cookies would be such a cute option for Halloween – whether brought to a party or tucked into your child’s lunch box. (Personally, I loved serving them for coffee with friends. Moms get to have fun, too!)
Ingredients for Jack O’Lantern Sandwich Cookies
- 3/4 cup unsalted butter, room temperature
- 3/4 cup sugar
- 1 large egg
- 2 teaspoons vanilla extract
- 2 cups flour
- 1/2 teaspoon baking powder
- 1/4 teaspoon salt
- Orange food dye
Chocolate Ganache Filling
- 1 cup chopped chocolate
- ½ cup heavy cream
Tip: if you love your pumpkin spice, feel free to add some to either the cookie dough or the ganache.
Kitchen Tools You May Find Helpful
- Jack O’Lantern sugar cookie cutter
- 2 disposable piping bags fitted with a number 2 tip
- 1 squeeze bottle
- Measuring cups and spoons
- Electric mixer
- Cutting board
- Rolling pin
- Cookie Sheets
- Cooling racks
- Small pot
- Heat-safe bowl
How to Make Jack O’Lantern Cookies
Preheat oven to 350 degrees
Cover two cookie sheets with parchment paper and set aside
Place the butter and sugar in a large bowl and beat until light and fluffy, about 2 minutes.
Add the egg and vanilla extract, and beat to incorporate, about 2 minutes.
In a small separate bowl, whisk together the flour, baking powder and salt. Add half of the flour mixture to the sugar-butter mixture, combine, and then add the remaining half.
Lightly flour a cutting board and knead the cookie dough a couple of times
Roll out the dough to about 1/2 inch thick.
Cut out your pumpkin or Jack O’Lantern cookie shapes, re-rolling out the dough as needed, and place onto the prepared cookie sheets.
Bake for 8-12 minutes or until lightly golden brown at the edges.
Let cookies cool completely.
To make the ganache, place the chocolate in a medium-sized microwave-safe bowl.
Place the heavy cream in a small pot over medium heat and bring to a boil. Pour immediately over the chocolate, and stir to melt. Let cool slightly before applying to the cookies.
Spoon the melted ganache into the center of the bottom cookie and then sandwich on the top cookie. Repeat with all cookies.
Grab your free printable for our fun Jack O’Lantern Milano cookie recipe:
Jack O’Lantern Sugar Cookies
These fun pumpkin sandwich cookies are a delicious Halloween twist on the classic Milano cookies – perfect for adults and kids!