Jack O’Lantern Sugar Cookies

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A fun twist on Pumpkin Sugar Cookies, these Jack O’Lantern cookies taste like a homemade Milano cookie – but with a fun Halloween twist!

These Jack O Lantern cookies are a fun twist on sandwich cookies - the perfect Halloween cookie for adults

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.

 

Pin this fun Halloween Milano Cookie recipe:

A fun twist on Pumpkin Sugar Cookies, these Jack O'Lantern cookies taste like a homemade Milano cookie - but with a fun Halloween twist!

Grab your free printable for our fun Jack O’Lantern Milano cookie recipe:

 

Jack O’Lantern Sugar Cookies

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These fun pumpkin sandwich cookies are a delicious Halloween twist on the classic Milano cookies – perfect for adults and kids!

For more delicious Halloween recipes, check out our Slice and Bake Pumpkin Sugar Cookies or our Spooky Ghost Carrot Cake.

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3 Comments

  1. Do you know if the cookie cutter is available anymore? I followed your link and it goes to a different product now and I’m having trouble finding something similar. I really want to make these! Thanks!

    1. Hi Rachel – thanks for letting me know! I’m actually in the process of updating ALL of my fall content right now, so I’m moving this further up the list!
      This one is similar to the one I used: https://amzn.to/2CJ9jC4 I’ll let you know if I find a link to the exact one. I’m thinking they’ve discontinued it.

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