Jack-O’-Lantern Halloween Cookies

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Jack-O’-Lantern Halloween Cookies are sure to put a smile on your face! Chewy cookies layered with milk chocolate and topped with cinnamon sugar, they’re the perfect tasty treats for spooky season.

Halloween season is here. That means it’s time for Spider Rice Krispie Treats, Halloween Dirt Cake and our other favorite fun and spooky Halloween muddy buddies.

Jack O Lantern pumpkin cookie filled with chocolate.
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Why These Halloween Cookies are Best

Pumpkins aren’t the only thing you can carve on Halloween. These easy cut-out cookies are shaped like pumpkins with a face carved right into each one.

  • Pumpkin shaped cookies carved just like a jack-o’-lantern!
  • Sandwiched with melted milk chocolate.
  • Perfect cinnamon sugar topping.
  • No food dye or frosting needed.
  • An eye-catching Halloween dessert that’s easy to make!

The milk chocolate gives them that “hollow” appearance just like a real jack-o-lantern while adding a creamy sweet layer in the middle of the cookie.

The only question is whether you’ll give your Halloween Jack-o’-lantern cookies a frightening face or a silly smile?

Either way, these creative cookies are sure to turn a few heads at your next Halloween bash. Give our candy corn sugar cookies a try next time you’re feeling creative! Or try our christmas tree sugar cookies for your next holiday.

Ingredient Notes

Cut out cookies shaped like pumpkin faces before baking.
  • Dark brown sugar – The dark color helps give the cookies their golden hue without the need of yellow or orange dyes.
  • Vanilla extract – Vanilla is the primary flavor of the sugar cookies themselves, so it’s always best to use a good quality pure extract, or use our homemade vanilla extract recipe to save money!
  • Milk chocolate morsels – Melted in the microwave or on a double boiler, this creates the chocolate center for the sandwich cookies. You could also use Nutella if you prefer!
  • Unsalted butter – Melted and brushed on top of the baked cookies to help the cinnamon sugar stick.
  • Cinnamon sugar- A combination of ground cinnamon and cinnamon sugar gives these cookies a delicious hint of fall spice and picture-perfect finished appearance. We’ve got the best tips and tricks on making your own cinnamon sugar mix.

Tips and Tricks

Melted chocolate and cinnamon sugar mix in bowls with pumpkin cut out cookies before assembly.

We used a simple cut-out sugar cookie dough as the base for these Halloween Jack-O’-Lantern cookies.

  • After making, chilling and cutting out the dough into pumpkin shapes, it’s time to turn them into jack-o’-lanterns!
  • Use a sharp knife to cut out eyes and a mouth in half the cookies. Leave the other half of the cookies uncarved. Bake all the cookies until lightly golden.

Now that your Jack-o’-lantern cookies are baked and cooled, here’s how to assemble them.

  • Brush each cookie with melted butter. Sprinkle cinnamon sugar on top.
  • Spread a layer of melted milk chocolate over the uncarved cookies.
  • Cover each one with a carved jack-o’-lantern cookie.

Don’t they look so fun? They taste even better with that delicious (and underrated!) combination of cinnamon and chocolate.

Pumpkin sandwich cookies with a bite taken out.

Recipe FAQs

Are these cookies pumpkin flavored?

These cookies are not pumpkin flavored. They’re just cut into pumpkin shapes. If you want to give the cookies even more fall flavor, you can add a teaspoon of Pumpkin Pie Spice to the dough. So easy and delicious!

What kind of cookie cutter do I need?

You can use any standard size pumpkin cookie cutter to cut out the cookie dough.
To save time, use a jack-o’-lantern cookie cutter like this one for half the cookies, instead of carving them by hand.
If you do use two different cookie cutters, just make sure the pumpkin outlines are the same size and shape so the finished cookies fit together.

How do you melt the chocolate morsels?

The easiest way to melt the chocolate is in the microwave. Heat them for 30 seconds at a time, then stir well. Repeat until the chocolate is smooth and melted.

How do I store Halloween cookies?

You can store these Halloween Cookies at room temperature for up to 3 days. If your house runs warm, I recommend storing them in the refrigerator. They taste great chilled.

Halloween shaped cookies with chocolate filling.

More Fall Baking

Easy Cookie Recipes

See all Cookies recipes

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Jack-O’-Lantern Halloween Cookies

5 from 5 votes
By: Aimee
Jack-O'-Lantern Halloween Cookies are sure to put a smile on your face! Chewy cookies layered with milk chocolate and topped with cinnamon sugar, they're the perfect tasty treats for spooky season
Prep Time: 30 minutes
Cook Time: 10 minutes
Chill Time: 1 hour
Total Time: 1 hour 40 minutes
Servings: 18 sandwich cookies


For the Cookies

  • 4 cups all-purpose flour
  • 1 teaspoon baking soda
  • ¼ teaspoon kosher salt
  • 1 cup unsalted butter softened
  • 1 cup dark brown sugar packed
  • 1 Tablespoon vanilla extract
  • 2 large eggs

For the Filling and Topping

  • 1 Tablespoon cinnamon
  • ¼ cup granulated sugar
  • 2 Tablespoons unsalted butter melted
  • 8 ounce milk chocolate morsels
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  • Preheat your oven to 350 degrees F. Line your cookie sheet with parchment paper and set aside.    
  • Combine the flour, baking soda, and salt in a bowl and keep aside.   
  • In a stand mixer (you can also use the hand mixer for this) add the softened butter, brown sugar, and vanilla. Beat at medium speed, scraping down the sides of the bowl as needed, for at least 2-3 min or until the mixture is creamy.    
  • Add in the eggs and beat until blended into the cookie dough.    
  • Add the flour mixture to the butter mixture in batches and mix just until the dough is formed.     
  • Flatten the dough to form a large disc, wrap it with plastic wrap, and refrigerate for at least an hour.     
  • Once chilled, roll out the dough on a lightly floured surface to 1/4-inch thickness and cut out pumpkin
    shapes using a pumpkin cookie cutter.    
  • Transfer the cut-out cookies carefully to the prepared baking tray and then use a sharp knife to carve out eyes and mouths as you like in half of the cookies (or use a cookie cutter that has the face shapes).
  • Roll the leftover dough and repeat the process.    
  • Bake in a preheated oven for 11-13 minutes or until they begin to turn golden-brown.
  • Let the cookies cool for 5 minutes on the cookie sheet before transferring them to a wire rack to cool completely.    
  • Combine cinnamon with sugar for the topping. Brush melted butter on top of the cooled cookies and then sprinkle cinnamon sugar on top.   
  • Assembling – Apply a layer of the melted chocolate on the base cookie and then place the carved-out cookie on top. Press gently.    


  • Store HALLOWEEN JACK-O-LANTERN COOKIES in an airtight container for 3 days at room temperature or in the refrigerator.       
  • You can add ground cinnamon, nutmeg, ginger, and all-spice powder to the cookies for an extra kick of warm flavors. Or add a teaspoon of pumpkin pie spice to the cookie dough.


Serving: 1cookie, Calories: 331kcal, Carbohydrates: 42g, Protein: 5g, Fat: 16g, Saturated Fat: 10g, Polyunsaturated Fat: 5g, Cholesterol: 54mg, Sodium: 110mg, Fiber: 1g, Sugar: 19g
Course: Cookies
Cuisine: American
Did you make this recipe?Mention @shugarysweets or tag #shugarysweets!

Jack-O’-Lantern Halloween Cookies are the perfect pumpkin shaped dessert for any Halloween party!

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About Aimee

Aimee is a dessert lover (specifically rice krispie treats), workout enthusiast, self-taught foodie, and recipe creator.

Learn more about Aimee.

Affiliate Disclosure:**There may be affiliate links in this post! By clicking on them, or purchasing recommended items I may receive a small compensation. However, I only recommend products I love! Thank you for supporting Shugary Sweets! See my disclosure policy for more info**

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Posted on September 12, 2022

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