Milk Chocolate Stuffed Jack-o-Lantern Cookies

Happy (almost) Halloween!

Every year for Halloween, I try to make the girls some festive treats to eat (I’ve made a bunch – you can take a peak at them here)! There’s everything from sweet to savory, breakfast to dessert and more!

This year, I wanted to make something to eat on the go as we head out for our beloved nature walks. We are keeping pretty socially distanced this year, so everything we can do to make it feel like a ‘normal’ year helps!

These cookies are a true win in this case! They are pumpkin shaped filled chocolate cookies with a snicker-doodle like outside. They’re pillowy soft and gooey right out of the oven. And they taste absolutely delicious. They’re a Halloween win from the kids in the neighborhood and the kids that live in our spooky house. 🙂

I hope you love them too – if you do, you can thank Half Baked Harvest as these are another gem of hers! Happy Halloween!


Milk Chocolate Stuffed Jack-o-Lantern Cookies

  • Servings: 45
  • Difficulty: easy
  • Print


  • 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

Cinnamon Sugar Coating

  • 2 tablespoons salted butter
  • 3 tablespoons cinnamon sugar


  1. 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, and mix until evenly combined. Add the flour, baking soda, cinnamon, ginger, nutmeg, and salt, beat until combined and the dough forms a ball.

  2. 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. Make sure you’re using enough flour or your dough will stick. Cut out the cookies using a pumpkin cookie cutter. Carefully transfer the cookies to a parchment lined baking sheet. Cut eyes and a mouth in half the cookies using a pairing knife or cookie cutter. Cover the baking sheet and place the sheet in the freezer, freeze until firm, about 15-20 minutes. Roll out the leftover scraps, and repeat with the remaining disk of dough.

  3. Preheat oven to 350 degrees. Bake the cookies on the middle rack of the oven for 8-12 minutes (for soft cookies) or until just lightly golden brown. Do not over bake. Cool on the baking sheet five minutes and then transfer to a wire cooling rack to cool completely.
  4. Add the butter to medium pot. Allow the butter to slightly brown until it smells toasted, about 2-3 minutes. Stir often. Remove from the heat and let cool 5 minutes. Brush the butter over the top half of the cookies and then sprinkle the cookies with cinnamon sugar.
  5. To assemble, spread the melted milk chocolate over the half of the cookies with no face. Place the top pumpkin faced cookies over the chocolate, gently pressing to adhere. Cookies can be served immediately or let the chocolate firm up and store in an airtight container for up to 3 days. Enjoy!

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