Cook on a Whim: Chocolate Ganache-Filled Jack-o’-Lantern Cookies

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 and 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.

Okay, confession time: Halloween is not and has never been my favorite holiday. Like, I’d be okay 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.

These cookies are filled with a soft chocolate ganache. They keep for days and somehow don’t dry out, but become more soft and tender with each passing day. A miracle?

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.

I should add that cutout cookies and decorated cookies are usually the kinds of recipes I avoid. They are just too finicky and fiddly for me. But this dough is a dream to work with and 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.

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!


Chocolate Ganache-Filled Jack-o’-Lantern Cookies



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

For the ganache:

2 cups chocolate chips (I used half milk and half bittersweet)

1 cup heavy cream

For the cinnamon sugar coating:

4 tablespoons salted butter

1 cup of cinnamon sugar



For the ganache:

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.

For the 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 to 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.

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 and freeze until firm, about 15 to 20 minutes. Roll out the leftover scraps and repeat with the remaining disk of dough.

Preheat oven to 350 degrees. Bake the cookies on the middle rack of the oven for 8 to 12 minutes (for soft cookies) or until just lightly golden brown. Do not overbake. Cool on the baking sheet for 5 minutes and then transfer to a wire cooling rack to cool completely.

Melt butter either in microwave or on stovetop. 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.

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.

Photo by Anita Parris Soule. Courtesy Cook on a Whim.


  • 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. 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 overbake. You want a nice, soft sugar cookie. I found 9 minutes to be perfect.

Recipe adapted from Half Baked Harvest.

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