Looking for something yummy and unique to bring to a Halloween party? Or just to enjoy yourself?! Look no further my friend, you’ve found the prefect recipe!
These Jack-O-Lantern sugar cookies are such a fun treat to make! And just look at how cute they are!
I know that some people love to go all out and do the creepy crawly snacks and treats for Halloween. But not me! I like to keep things a little more on the cute side around here. After all, I’m not looking to gross or creep my kids out! They’re still very young (and picky). So these Jack-O-Lantern chocolate filled sugar cookies are always a smash hit with my littles. And I can see why!
They are sweet, chocolatey, totally adorable, and easily transportable in all their cookie sandwich style glory. Plus, a LOT of fun for the kids to help make. What’s not to love?!
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Equipment needed to make Jack-O-Lantern Sugar Cookies
- Stand Mixer
- Spatula
- Baking Sheet
- Small Mixing Bowl
- Small Cooking Pot
- Pumpkin Shaped Cookie Cutter
- Sharp Knife
Ingredients to make Jack-O-Lantern Sugar Cookies
For the Cookies
- Unsalted butter (at room temperature)
- Brown Sugar
- Vanilla Extract
- Eggs
- Unbleached All Purpose Flour
- Cinnamon
- Baking Soda
- Salt
- Semi Sweet or Milk Chocolate (melted)
For the Cinnamon Sugar Topping
- Salted Butter (melted)
- Cinnamon
- Granulated Sugar
Instructions to make Jack-O-Lantern Sugar Cookies
Making the Cookies
1. In a stand mixer, us the whisk attachment to combine room temperature butter, brown sugar and vanilla extract. Mix until light and fluffy.
2. Next, add the eggs one at a time. Mixing after each addition.
3. Once the eggs are well incorporated, add all of the dry ingredients to the bowl. Mix until well combined and dough no longer sticks to the sides of the bowl.
4. Generously flour your work surface.
5. Shape the dough into a large ball. Lightly roll it into a circular shape and divide in half.
6. Wrap one half the of dough with plastic wrap and place it into the fridge.
7. Then, roll the first half of the dough out until it is roughly 1/4 inch thick. Using a cookie cutter, cut the dough into pumpkin shapes. Continue this step until all or nearly all of the first half of the dough is used.
8. Place the pumpkin shaped dough in a single layer onto a baking sheet lined with wax paper.
9. Put the pan in the freezer for 10-15 minutes to chill the dough.
10. Preheat your oven to 350 degrees.
11. Take the second half of the dough out of your refrigerator and being rolling it out until it is about 1/4 inch think.
12. Just as before, cut the dough into pumpkins with a cookie cutter until all of the dough is used.
13. Using a small sharp knife, cut eyes and mouth into each cookie. These will be the top of the cookies where the chocolate filling oozes out from. YUM!
14. Once you have all of the faces cut out of the cookies, do as before and place them in a single layer onto a wax lined baking sheet. Place them into the freezer for approximately 15 minutes to chill.
15. Once the dough has chilled and your oven is preheated, place the cookies into the oven. Bake for 15 minutes until just lightly golden brown.
16. Let the cookies rest on the pan for two minutes before transferring them onto a cooling rack.
17. Let the cookies cool completely before moving onto the next step.
18. After the cookies are cooled, melt the chocolate (semi-sweet or milk chocolate) on the stove top.
19. Let the melted chocolate cool slightly before working with it.
20. While the chocolate filling is cooling down slightly, prepare the cinnamon sugar topping. (directions below)
Making the Cinnamon Sugar Topping
1. Melt the butter on the stove top until lightly browned.
2. Let the melted butter cool for a moment while mixing together the cinnamon sugar topping.
3. Mix together 2-3 Tablespoons of sugar and 1 teaspoon of cinnamon. This is the topping for the face of the cookies.
4. Set aside until ready to use.
Finishing up the Jack-O-Lantern Sugar Cookies
21. Once you have the cinnamon sugar topping mixed together, brush the face of the cookies with the melted butter and dip in the cinnamon sugar topping to coat them. Continue this step until all of the cookies faces are covered with the cinnamon sugar topping.
22. Now, using a flexible spatula, spread 1.5-2 Tablespoons of the melted chocolate onto one of the solid pumpkin shaped cookie. Top it with one of the cinnamon sugared face cookies and press together. Do this with all the of the remaining cookies.
And just like that, you’re done! You’ve made quite possibly some of the most adorable cookies ever!
Keep them all for yourself (no judgement here), or WOW your friends and family with your impressive baking skills!
A Great Party Activity!
To make this a fun Halloween Party or even Thanksgiving get together activity, go ahead and get everything made beforehand. Mix together the cinnamon sugar topping and shape and bake the cookies.
All that’s left to do at the time is melt the chocolate and butter! So do that then lay everything out on a table and turn this into a cookie making station for your guests! It’s a HUGE hit with kids, but I know plenty of adults’ who would enjoy themselves while doing this too. 😏 Me included!
A Few Variations Worth Trying
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 or Nutella would also make delicious fillings for these cookies. So if that’s more your style or taste, give it a try!
How to Store 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, haha!
I hope you go ahead and give these cookies a try because I don’t think you’ll be disappointed my friend!
Tried and liked this recipe? Give it a rating and leave a comment below! Then snap a photo and tag us over on IG @ _jchandelle
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Jack-O-Lantern Cinnamon and Brown Sugar Cookies with Chocolate Filling
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
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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!
