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Fridays require something sweet, enter these Milk Chocolate Stuffed Jack O’ Lantern Cookies. Sweet milk chocolate, sandwiched between spiced brown sugar cookies, and finished with a light dusting of cinnamon sugar. There’s nothing not to love about this cookie sandwich. Perfect for both a spooky Halloween night, or an elegant Thanksgiving dinner…or just when you need a deliciously sweet chocolate filled cookie.
This is one of those Fridays that I’m so excited for.
One, it’s just been a very, very long week. Lots of good things, plenty of cooking, one afternoon/night of not feeling well (probably due to lack of sleep), so much pretty white snow, cold temperatures, and a whole slew of other things. It’s safe to say that I’m ready for the weekend…and my inbox to slow down for a couple of days.
Two, we have cookies to talk about. Delicious, cute, chocolate filled cookies, that are the quintessential autumn dessert.
I’m obsessed with these cookies and have been so excited to share them with you guys!
Aside from their major cuteness factor, these jack-o-lantern cookies are honestly so good.
The cookie itself is a brown sugar cookie that’s been spiced with cinnamon, ginger, and nutmeg. I wanted the cookie to really have that “spiced” flavor and taste sweet and warming with every bite. It is a fall cookie after all! That said, I didn’t include any pumpkin in my cookies. I just don’t think it’s needed every time I make a pumpkin cookie. Pumpkin often causes the cookie to turn out cakey…and I’m not the biggest fan of cakey cookies. So no pumpkin here, just pumpkin shaped!
Speaking of which, I’ve been searching unsuccessfully for the exact cookie cutter I used to make these. I wanted to give you guys the link. It’s an old Target cookie cutter, probably over five years old now. Sadly, I’m guessing it’s no longer available. Oh well, I found some just as cute ones that I really wish I had right now.
These cookie cutters are my favorite, and would make for really fun cookies. I love that each cookie would be unique. This cookie cutter would give you more of the look of my cookie, but I think they’d be just a bit bigger. Also, I have this cutter and love it, but it does not have a face. Any of these options work great! And then of course, if you already have a pumpkin cookie cutter, use that. Then just cut out eyes using a sharp paring knife.
Don’t stress about making the cookies look perfect either. If you’re making these for Halloween, the more messed up they are, they spookier, which is perfect.
For the filling, I knew I wanted it to be straight up milk chocolate. Sometimes you need a good dark chocolate moment in your life, and sometimes life just calls for milk chocolate…preferably melted and sandwiched between these cookies.
Today is a milk chocolate day cookie day.
Go with me on this, you will be so happy you did.
To give each cookie a little sparkle, I dusted them lightly with cinnamon sugar.
Yes, yes, yes…sugar cookies, milk chocolate, and cinnamon sugar. All things sweet, all things perfect, and everything you need out of a cookie right now. There’s even a little browned butter too.
If you’re doing cookies, you might as well do them up right, you know?
Make these tonight, make them this weekend, or maybe even for Halloween. And then maybe even again for Thanksgiving. It doesn’t matter, just make them soon. Trust me, you’ll be making batch after batch because these cookies are that good.
If you make these jack-o’-lantern cookies please be sure to leave a comment and/or give this recipe a rating! Above all, I love to hear from you guys and always do my best to respond to each and every comment. And of course, if you do make this recipe, don’t forget to also tag me on Instagram! Looking through the photos of recipes you all have made is my favorite!
Milk Chocolate Stuffed Jack-O'-Lantern Cookies
Ingredients
- 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
- 12 ounces milk chocolate, melted
Cinnamon Sugar Coating
- 2 tablespoons salted butter
- 3 tablespoons cinnamon sugar
Instructions
- 1. In a large mixing bowl, cream together the butter, sugar, and vanilla until light and fluffy, about 3-5 minutes. Add the eggs, one at a time, 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. Cut out the cookies using a pumpkin cookie cutter. Carefully transfer the cookies to a parchment lined baking sheet. Cut eyes and a mouth in half the cookies using a pairing knife or cookie cutter. Cover the baking sheet and 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, Add the butter to medium pot. Allow the butter to slightly brown until it smells toasted, about 2-3 minutes. Stir often. Remove from the heat and let cool 5 minutes. Brush the butter over the top half of the cookies and then sprinkle the cookies with cinnamon sugar.5. To assemble, spread the melted milk chocolate 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 chocolate firm up and store in an airtight container for up to 3 days.
Notes
Nutrition
Nutritional information is only an estimate. The accuracy of the nutritional information for any recipe on this site is not guaranteed.
Did you make this recipe? Please rate & comment below.
My niece Alyssa and I loooved these! They were delicious and so adorable. Thanks for sharing xoxo
Thank you so much Julie! I am so happy you enjoyed this one! xTieghan
Wasted 3 hours trying to get the recipe to work out. I have never not succeeded at baking any cookies ive tried. I had very disappointed kids this year because of this. Cutter did not work well, dough was too soft to cut out faces, freezing did not help. Had to pitch entire thing. So not worth making
Hi Julie! I am really sorry this did not turn out well for you. Is there anything that could have gone wrong while making it? I would love to help! xTieghan
I made these today. I have no idea how you got them done in 45 minutes. It took about an hour just to roll out the dough and cut out the cookies. Then you have to freeze for 15-20. Which i didn’t do. Then they bake for 12 minutes. I also got 48 sandwich cookies and 16 single layer ones. I used a decent size cookie cutter too, not a small one.
I hope they are worth all the work.
Hi Emily! I am sorry these took longer than expected! I hope these still turned out amazing for you! xTieghan
There are no instructions of how to melt the chocolate or what exact type to use!
Hey T,
I like to use milk chocolate and simply melt in the microwave:) I hope you love the recipe, please let me know if you have any other questions! xTieghan
your cookie cutter links arent working
Hey Jack,
So sorry they aren’t working for you, but they are working on our end. I hope you love the recipe, please let me know if you have any other questions! xTieghan
Hello is it ground ginger or fresh ginger?
Hey Destiny,
You will want to use ground ginger. I hope you love the recipe, please let me know if you have any other questions! xTieghan
I hate to leave a negative comment, but these did not turn out for us at all. The dough was so, so sticky that it could hardly be rolled out. I kept adding flour to fix it and then they came out tasting just like flour. The eyes and mouth shapes also looked terrible (that’s on me). Curious how anyone rolled out this dough successfully without sacrificing the flavor.
Hi Mari! I am really sorry to hear that! Is there anything that could have been changed while making this? I would love to help! xTieghan
hi tieghan, i’m so excited to make these this weekend as a gift for a friend! i am used to measuring flour in scales, and was just wondering if when you measure flour you spoon and level/if you have a weight estimate!
thanks!
Hi Isabel! I spoon and level a cup measurement! I hope this helps! Please let me know if you have any other questions! xTieghan
I haven’t made these yet as I’m waiting for my granddaughter this weekend! Was wondering if I can use chocolate buttercream frosting instead of chocolate?thanks, Ann
Hey Andrea,
Yes that would work. I hope you love the recipe, please let me know if you have any other questions! xTieghan
Made these for my nieces and nephews last week. They were super easy and a big hit with the both the kids and adults! My pumpkin cutter did not have eyes or a nose, so I cut those out with a paring knife. I was afraid they would fill in while the cookie baked, but I think the tip to freeze them before baking did the trick and they looked so cute! In fact, I liked these cookies so much that I am thinking about making them for Christmas with a gingerbread man cookie cutter.
Ooo love that! I am so glad these turned out so well for you! xTieghan
Totally made these for Halloween and they turned out so good!! Love the texture and the spices with the milk chocolate. The cinnamon sugar really took it over the top. Also really impressed because usually my sugar cookie dough sticks really bad but this one was really easy to work with! We ended up using a knife to cut out faces and we actually really loved that because each one had its own little mini vibe and they all looked so silly or crazy, it cracked everybody up. So I highly recommend cutting faces out sometime because it adds a whole new fun element to the recipe!! This will be an every Halloween recipe for sure, thank you for the share!!
Thank you Elle! I am so glad these turned out so well for you! xTieghan
Love these adorable cookies! They taste delicious — my daughter loved helping us make them into little cookie sandwiches!!
One issue: rolling the dough 1/4 inch made the cookies too thick, but the thinner versions broke when we tried to lift the dough. Any idea where we went awry? We do live at 8000 ft… Cheers!
Hey Rachel!! For a thinner cookie, use a metal spatula dusted with flour to lift the cookie off the counter and onto the cookie sheet OR roll the cookie out between 2 pieces of parchment paper. Either option should solve the issue of the dough breaking on you! Please let me know if you have any other questions. I am so glad you guys love this recipe! Thank you! xTieghan ??
I cannot wait to make these cookies this weekend! Thank you for linking the cookie cutters! Can I make the dough ahead of time and store it in the freezer before rolling it out and baking it?
HI! Yes that works really well! Please let me know if you have any other questions. I hope you love this recipe! Thank you! xTieghan ???
Could you use Nutella in this recipe instead of the milk chocolate?
Hi Jenn! I am sure Nutella will be delicious. Great idea! Please let me know if you have any other questions. I hope you love this recipe! Thank you! xTieghan ???
Making these now, I hope they are good! Taking me forever to make!
I hope you love these Elizabeth! Let me know how they turn out for you! xTieghan