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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 5 year old and I had a blast making these together today!! Best part is we had all the ingredients so super easy to make on a lazy Saturday!
I am so glad you and your daughter loved making these and they turned out well for you! Thank you Michelle!
Will these cookies be good as next day cookies? I’d like to make them for a party, and I’d have to do them the night before (being served at lunch the next day). I’m afraid they might get too soggy or something.
Hey Nina! These cookies are great the next day!! Please let me know if you have any other questions. I hope you love this recipe. Thanks so much! xTieghan
These are adorable!!
Thank you Deborah!
Excelente idea!!! Wonderful idea!!
Thank you Marta!
These look fantastic!!
Rebecca | http://www.peppermintdolly.com
Thank you Rebecca!
Oh my, what a cute cute cookie!!
Can’t believe you already have snow; it’s 78° in south of France and I’m still scrolling through your summer recipes. Back to this cutie, we don’t do Halloween here (and don’t eat much pumpkin either) but I love all these creative and pretty recipes you offer in October. Sending some warmth along, à bientôt!
Thank you so much Anaïs! I am so glad you love these!
These are almost too cute to eat. They bring a smile to my face. I’d ALMOST feel sad, I said almost, biting into one of these. I’ll have to give them a try. I like the twist on these with the autumn spices in the cookie.
Thank you so much! I hope you love them!
These are adorable! I don’t have a pumpkin cookie cutter but might just make them as circle sandwich cookies.. def not as cute but probably still delicious!
Thank you so much Gillian! I am so glad you are loving these cookies and I am sure they would be so great as just circles!
hey girl- these are so cool! yummy! Have a great weekend!
Thank you so much Shawnna! I hope you love this!
Was able to order the exact cookie cutter you used on Amazon – ordered and will be making for my Daisy girl scouts next Monday. Will make again for Thanksgiving – a nice addition to pie.
That is so sweet! I hope they all love these cookies, Debbi! Thank you so much!
Yay, I love when you do nut-free desserts (although I do like LOOKING at all the peanut butter goodness too haha)! I definitely think I’m going to be trying this soon.
You totally should! I hope you love this Victoria! Thank you!
I’ve ordered the cookie cutter from etsy and i’m SO excited to make these!
Perfect! I hope you love this Charlotte!
Well Tieghan….I was just thInking I wanted to make cookies today. Forgot I had a pumpkin cookie cutter! Do you think some Nutella might work inbetween those cookies?
HI! Nutella will be so delicious. Great idea! Please let me know if you have any other questions. I hope you love this recipe. Thanks so much! xTieghan
It seems so delicious
Thank you!
This is officially my favorite Halloween cookie of 2018. I mean, how cute, yet spooky do these look. And thanks for linking the cookie cutter, buying it right now! Hooray!
I am so glad! I hope these turn out amazing for you, when you make them Maja!!