Jack-O-Lantern Cinnamon and Brown Sugar Cookies with Chocolate Filling
A simple to make and sweet to eat, cinnamon and sugar chocolate filled Jack-O-Lantern cookie! Make these for a Halloween or Thanksgiving get together and wow your guests. Or make them all for yourself!
Equipment
- 1 stand mixer
- 1 spatula
- 1 baking sheet
- 1 small mixing bowl
- 1 small cooking pot
- 1 pumpkin shaped cookie cutter
- 1 small sharp knife
Ingredients
For the Cookies
- 3 sticks unsalted butter room temperature
- 1 ¼ cup packed brown sugar
- 1 tablespoon vanilla or almond extract
- 2 large eggs
- 4.5 cups unbleached all purpose flour
- 1 teaspoon baking soda
- 1 teaspoon cinnamon
- ½ teaspoon salt
- 12 ounces semi-sweet, milk or white chocolate melted, for the filling
For the Topping
- 2 tablespoons salted butter melted
- 2-3 tablespoons granulated sugar
- 1 teaspoon cinnamon
I earn a commission from Instacart from qualifying purchases.
Instructions
Making the cookie dough
- In the bowl of a stand mixer, combine the softened butter, sugar and vanilla (or almond) extract. Mix for a few minutes, until light and fluffy.
- Add the eggs one at a time, mixing after each addition until very well incorporated.
- Add all of the dry ingredients to the wet ingredients and mix until combined and dough isn't sticking to the sides of the bowl.
- Generously flour your work surface.
- Turn the dough out onto the floured surface, shape into a ball and divide in half.
- Wrap one half of the dough in plastic wrap and place into the refrigerator.
- Roll out the other half of the dough until it is about 1/4 inch think. With your pumpkin shaped cookie cutter, cut the dough. Do this until all of the dough is used or there isn't enough left to form another pumpkin.
- Line a baking sheet with wax paper. Place the shaped cookies on to the baking sheet and put them into the freezer for 15 minutes to chill before baking.
- Preheat your oven to 350 degrees.
- Next, take the second half of the dough out of the refrigerator and do as you did with the first half. Roll the dough out to about 1/4 inch thickness and cut with your cookie cutter into pumpkins.
- Once you have cut the dough into pumpkins, use a small sharp knife to cut out the eyes and mouths of the pumpkins.
- When done, place the cookies on a wax lined baking sheet and chill them in the freezer for `5 minutes before baking.
- Once the cookies have chilled and your oven is heated to temperature, cook the cookies for 15 minutes or until lightly golden brown.
- Once the cookies are baked, let them rest of the pan for 2 minutes before transferring them onto a cooling rack to cool completely.
Making the cinnamon sugar topping
- Melt 2 tablespoons of salted butter in a small pot on the stove until lightly browned.
- In a small bowl combine 2-3 tablespoons of granulated sugar and 1 teaspoon of cinnamon. Mix well.
- Brush the tops of the baked cookies that have the faces cut out of them, and dip into the cinnamon sugar mix.
Making the filling
- Melt 12 ounces of semi-sweet, milk or white chocolate either on the stove top or in a microwave.
- Let it cool slightly before using,
Assembling the cookies
- Once the cookies have cooled, the chocolate filling has slightly cooled and the cookies with the faces have been dipped in the cinnamon sugar topping, it's time to assemble!Grab one of the solid pumpkin shaped cookies and spread 1-2 tablespoons of the melted chocolate onto it.Then top it with one of the cinnamon sugar topped face cookies and press together like a sandwich.Repeat until all of the cookies have been made into cookie sandwiches!And viola, you're done!
Notes
Flavor variations
My family and I aren’t huge Nutmeg fans. But if that’s a flavor you like, then go ahead and add a Teaspoon of Nutmeg to the cookie dough recipe!
The same goes for Ginger! We don’t particularly care for it so we don’t incorporate it. But if you’d like to, then just add a 1/2 Teaspoon or so to the cookie dough. A little goes a long way.
While I love all things Almond, I do prefer Vanilla extract for these cookies. However, they can just as easily be made with Almond extract and still taste fantastic.
White Chocolate would also be a GREAT filling for these cookies. So if that’s more your style or taste, go for it!
Storing the cookies
So, you can shape the cookies and store them in the freezer until you’re ready to use them.
However, once baked, store them in an air tight container for up to 1 week. Anything longer than that and you’ll have to eat them at your own discretion!
