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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
Servings: 30 (30 cookies)
Calories Per Serving: 254 kcal
Nutritional information is only an estimate. The accuracy of the nutritional information for any recipe on this site is not guaranteed.
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
*I recommend these cookie cutters.
*If you don't have a pumpkin cookie cutter, just simple cut out 3 inch circles and use a sharp pairing knife to make the eyes and mouth.
This post was originally published on October 12, 2018
Might be a silly question, but when you stick them in the freezer have you already removed the extra pieces of dough yet? Or does the freezing help make it easier to remove the extra dough pieces?
Hey Brooke, you should remove the extra pieces of dough before freezing. Please let me know if you have any other questions. I hope you love this recipe! Thank you! xTieghan ???
Quick question!! Can I freeze the cookie dough to do the rest another day?
I don’t see why you couldn’t freeze the dough and make them another day. That sounds like a fantastic way to let the fun of Halloween last even longer throughout the month. Enjoy! Let us know if you have any questions.
These look delicious. Could you re-share the exact cookie cutter link? I’m getting a different product. Love all your recipes!
Hi Melissa! Thank you! There isn’t a link for the exact cutter up any more but this is as close as you can get https://rstyle.me/n/c9457zb9wzf
Another idea is to snap the stem off the base cookie, so there’s only one stem.
Thank you Anita! xTieghan
I made these and they are gorgeous and delicious. I used the jack-o-lantern cutter in this set: https://www.amazon.com/gp/product/B07GFNP5TH/ref=ppx_yo_dt_b_asin_title_o00_s00?ie=UTF8&psc=1. But, I was having a difficult time making nice cutouts. My husband figured out how to detach the inner face from the outer, main cutter – this was the hack I needed -was amazing. One other note: If you cut the bottoms/background pumpkins in the same direction as the face pumpkins, and want to put the chocolate on the flat side, the stems will go in opposite direction – so you can use the back side of the cutter to cut out the base – just be careful, because the sharper side will be facing up.
I am so happy to hear that these turned out so well for you, Anita! Thank you so much! xTieghan
I made these tonight and they were amazing! I made some with chocolate, and some without. The brown butter on top really made the flavors sing. Thanks for the great recipe 🙂
I am so glad you loved these and they turned out amazing for you! Thank you so much!
Made these cookies the other night to add to my Halloween treat bags I was taking to work. They were so cute and everyone loved them! The cookies by themselves are a little bland so I wouldn’t suggest making these as a stand alone cookie, but when filled with the milk chocolate they were perfect. I used a pumpkin cookie cutter to cut out the pumpkin shapes and a paring knife for the eyes and smiles. I learned bigger is better! The first batch, the eyes and mouth expanded and didn’t leave a hole as big as I wanted for the milk chocolate to peek through, but once I learned this I made the adjustments and the results were great. Thanks for sharing this one Tieghan. My co-workers thank you 😉
Thank you so much Kimiko! I am so glad you loved these cookies and they turned out amazing for you! Also, so sweet you added them to your treat bags!
Delicious! I made these (used dark brown sugar because it’s all i had) and they were great. Easy to make – assembly does take a bit longer though but super cute. They remind me of a Keebler fudge sandwich cookie but homemade and some extra cinnamon! Would definitely recommend making for a fun baking project.
I am so glad these turned out amazing for you and you enjoyed them Morgan! Thank you so much! I hope you had a great Halloween!
I rarely leave reviews, but these were the easiest cookies to roll out and cut. Made my second batch today to take to all the grandchildren, 14, on Halloween. Thanks for a great recipe.
Thank you so much Barbara! I am so glad you enjoyed these!
The recipe says it makes 30 cookies – is that 30 complete sandwiched cookies or 30 single cookies? Thanks!
HI! It is 30 sandwiched cookies. Please let me know if you have any other questions. I hope you love this recipe. Thanks so much! xTieghan
These are the most adorable cookies, I love them!!
Thank you!
I am definitely giving these a try! I am in the U.K. what would the measurement of sugar be in grams?
Hi Laurie! It is 250grams. I hope you love these cookies! Let me know how they turn out!
Hi Laurie! It’s about 250 grams of sugar. Please let me know if you have any other questions. I hope you love this recipe. Thanks so much! xTieghan
These are super cute and I’m making them for the office on Halloween! Question: what is the value of using salted butter as opposed to unsalted?
HI! I love using salted butter as I think it makes baked treats like cookies extra special. You can use unsalted butter, but add 1/2 to 1 teaspoon kosher salt to the dough. Please let me know if you have any other questions. I hope you love this recipe. Thanks so much! xTieghan
These were delicious! The spice in the cookie was my favorite part. Also, I liked how they weren’t super sweet. Definitely better the next day when the chocolate hardened, I used the Ghiardelli milk chocolate which I highly recommend! I found that the thinner, more lightly browned cookies were much better than the softer cookies! I’m not very good at evenly rolling cookies, so some cooked more than others 🙂 I made ghosts and pumpkins and they were so cute. I will definitely make these cookies again soon.
Thank you so much Ashley! I am so glad you loved this recipe and it turned out well for you!
I’m a bit confused. Are you putting the cookies right in the oven after freezing or waiting until they’re soft again?
HI! You should bake the cookies right after freezing. Please let me know if you have any other questions. I hope you love this recipe. Thanks so much! xTieghan