These Chocolate Ganache Filled Jack-O’-Lantern Cookies are the cutest and have finally given me an excuse to use the jack-o-lantern cookie cutters I bought ages ago. The dough is soft, buttery, and uses only brown sugar so you can imagine how delicious. Well then we add cinnamon, nutmeg, ginger, and vanilla. Yep, pretty much the perfect fall cookie. And you could make these in any shape all fall and winter long.
Ok, confession time: Halloween is not and has never been my favorite holiday. Like, I’d be ok if it didn’t exist. I see it as a hurdle we have to jump over to get to the good stuff: Thanksgiving and Christmas! I just don’t love candy very much and I don’t love being out at night (hello, homebody). But I could learn to love it more if I was snuggled up on the couch, safe from the ghouls and goblins, munching on these adorable and delicious cookies! Let’s talk about how to make them.
I can’t take credit for this recipe; these come courtesy of the endlessly talented and always inspiring Tieghan of Half Baked Harvest. I switched up the filling and opted for a chocolate ganache rather than just straight-up milk chocolate because I wanted a filling that would stay soft even after cooling, but the ingredients for the cookie dough are exactly as she has it written. I made a few changes to the process just based on how I like to do things, but she deserves all the credit here.
You can find her recipe and post here: Milk Chocolate Stuffed Jack-O’-Lantern Cookies
I actually don’t remember where I got these cutters, but you can find some cute, similar cutters on amazon.
I should add that cut-out cookies and decorated cookies are usually the kinds of recipes I avoid. They are just too finicky and fiddly for me. But when I saw Tieghan’s post on Instagram I remembered I had these long lost cookie cutters and I just had to give them a try.
The dough comes together in a snap as long as your butter and eggs are at room temp, which mine always are. It is a soft dough to work with, but just use plenty of flour when you roll them out and cut them. Also, I found when cutting them to go straight down and up. Don’t wiggle your cookie cutter. Every time I wiggled mine the dough would get stuck.
Another miracle of this dough is that it can be reshaped and re-rolled multiple times without sacrificing texture. I was able to use all but the tiniest little scraps and get a total of 48 cookies which made 24 sandwiches.
The freezing step is key to the cookies holding their shape, which again is another miracle and a reason I hardly make cutout cookies. Nobody wants to spend time cutting out cookies just to have them puff and spread in the oven and come out looking nothing like the cookie cutter. Good news: these cookies won’t do that to you.
Give these cookies a try. I hope you love them!
A soft, buttery, lightly spiced dough filled with rich chocolate ganache and coated in sweet cinnamon sugar.
- 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
- 2 cups chocolate chips (I used half milk and half bittersweet)
- 1 cup heavy cream
CINNAMON SUGAR COATING
- 4 tablespoons salted butter
- 1 cup of cinnamon sugar
Place chocolate in medium bowl.
Heat cream to just below a boil.
Pour cream over chocolate and let sit for 3 minutes.
gently whisk chocolate until you have a thick, creamy, shiny ganache.
Let cool to room temperature and allow to thicken slightly before filling cookies.
In a large mixing bowl, or stand mixer fitted with paddle attachment, cream together the butter, sugar, and vanilla until light and fluffy, about 3-5 minutes. Add the eggs, 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. Flour the top of the dough and dip your cookie cutter in dough too. You can’t be too careful.
Cut out the cookies using a pumpkin cookie cutter. If you have the solid pumpkin as well as the jack-o-lantern cutter, make sure you are making an equal amount of both.
Carefully transfer the cookies to a parchment lined baking sheet. 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. Melt butter either in microwave or on stove top. Brush the butter over the top half of the cookies and then sprinkle the cookies with cinnamon sugar. I like placing my cinnamon sugar in a large pie dish so I can just lay the cookies face down. You won’t use the whole cup, it just makes the process so much easier to have a large amount.
5. To assemble, spread the room temperature ganache 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 ganache firm up and store in an airtight container for up to 3 days.
If you don’t have the jack-o-lantern cutter, you can use a sharp knife to cut out faces. Or just use the solid pumpkin cutters and you’ll still have delicious and festive sandwich cookies.
Feel free to spice up the ganache too. The same spices that go into the cookies play really well with chocolate too. Or add some cinnamon and cayenne for a Mexican Chocolate twist.
The yield will depend on your cookie cutter. As long as you are rolling them to 1/4 inch thick, the cook time should still be the same. Just keep an eye and don’t over-bake. You want a nice, soft sugar cookie. I found 9 minutes to be perfect.
Keywords: halloween cookies, cookies, sugar cookies
Here’s a recipe to use up that leftover cinnamon sugar: