Jack O’ Lantern Cookies are so fun for kids and adults! The chocolate oozing through the face brings joy to every chocolate lover out there. The cookie itself has a brown sugar & spice taste to it. This cookie will last you well to Thanksgiving, but you can change up your cookie cutter and do one for each holiday!
Once the weather breaks, we love transitioning from grilling and fruit centered dishes, to baking and holiday-themed desserts. One of the first ones we worked on this fall is this recipe for Jack O’ Lantern Cookies. We typically don’t do cookie sandwiches…and to be honest, I have no idea why! This was a super fun cookie to create and it wasn’t too hard at all.
We love cookies that have a unique flair to them, so these are definitely not considered “boring cookies” to us. They are a conversation starter all on their own!
Creating the Jack O’ Lantern Cookies’ Face
The most time consuming part is the cutting out of the face on the top cookies. Now, if you have a jack o’ lantern cookie cutter complete with the face portion, that’s awesome! You can add this one to your Amazon cart. Total time saver for sure! However, we do not have one of these (it needs added to the list). So, we went old school with using a paring knife and got down with our freehand roots!
If you are going the same route as we did, start with two simple triangles on either side of the upper half of the pumpkin. Then, start the mouth. We found it easiest to start at the right or left mouth corner so we weren’t freehanding from the center. Add a crooked tooth here and there and you’re finished!
Jack O' Lantern Cookies
- 1 1/4 cups light brown sugar packed
- 1 tbsp vanilla extract
- 3 sticks salted butter room temperature
- 2 extra large eggs room temperature
- 4 1/2 cups all purpose flour
- 1 tsp baking soda
- 1 tsp cinnamon
- 1/4 tsp nutmeg
- 1/2 tsp salt
- 12 ounces milk chocolate melted
- Cream together the brown sugar, vanilla, and butter in a large mixing bowl (for about 3-5 minutes).
- Add one egg at a time. Mix each one in until combined.
- Beat in the flour, baking soda, cinnamon, nutmeg, and salt until combined. You want the dough to form a ball.
- Prep your work area with a good bit of flour (your dough will stick if you skimp on flour). Divide the cookie dough in half and flatten both halves into disks. Roll out the dough to 1/4 inch thickness.
- Start using your cookie cutter to form the pumpkins, then transfer them to a parchment lined baking sheet. If you do not have a cookie cutter with the face cut-outs included, you will have to use a paring knife to free hand the eyes and mouth (description of how to do this in the above article).
- Cover the baking sheet and put it in the freezer for about 20 minutes. Roll out the leftover scraps and repeat with the remaining cookie dough.
- Preheat your oven to 350 degrees F. Bake 8-14 minutes (depending on your oven) until just lightly golden brown. Allow to rest on the baking sheet for 5 minutes, then transfer to a cooling rack.
- Once all the top and bottom cookies are cooled completely, you will start to assemble your Jack O' Lantern Cookies. Spread the melted milk chocolate over the cookies that don't have a face (bottom of sandwich). Then, place the cookie with a face on top. Gently press together to allow some of the melted chocolate to ooze through the face.
The inspiration for this recipe came from Half Baked Harvest. Thank you so much! This will be a cookie passed down for years to come.
Everyone have a great Halloween and bake something up with your family soon! 🙂
Looking for some other Halloween-inspired recipes?