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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 these cookies. Perfect for both a spooky Halloween night, or an elegant Thanksgiving dinner…or just when you need a deliciously sweet chocolate filled cookie.

overhead photo of Milk Chocolate Stuffed Jack-O'-Lantern Cookies with mini pumpkins in photo

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!

Milk Chocolate Stuffed Jack-O'-Lantern Cookies | halfbakedharvest.com #halloween #thanksgiving #cookies #easyrecipes #chocolate #holidayrecipes #fallrecipes

Aside from their major cuteness factor, these 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!

close up side angle photo of Milk Chocolate Stuffed Jack-O'-Lantern Cookies

overhead photo of Milk Chocolate Stuffed Jack-O'-Lantern Cookies

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 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.

Milk Chocolate Stuffed Jack-O'-Lantern Cookies sitting on top of mini pumpkin

side angled photo Milk Chocolate Stuffed Jack-O'-Lantern Cookies

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.

close up overhead photo of Milk Chocolate Stuffed Jack-O'-Lantern Cookies on plate

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.

close up photo of Milk Chocolate Stuffed Jack-O'-Lantern Cookies on plate

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

Prep Time 30 minutes
Cook Time 15 minutes
Total Time 45 minutes
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.

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Ingredients

Cinnamon Sugar Coating

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. 
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Comments

  1. 5 stars
    Very excited to make these! Question: could I place chocolate morsels on the dough and bake? Or maybe bake as a sandwich? I am very bad at working with melted chocolate. Thank you!

    1. Hi Mel,
      So sorry, I am not sure what you mean:) I would not bake these as a sandwich. I promise the melted chocolate is super easy to work with:) Let me know if you give the recipe a try! xx

  2. 4 stars
    Followed the directions exactly and the dough was really dry and cracking. It was hard to form a dough ball and when rolled the cookie has cracks. How would I fix this… more butter?

    Made these for a party tonight and mine turned out ugly but they do taste delicious. 🙂

    1. Hi Alice,
      Thanks for giving the recipe a try, so sorry to hear about the dough! Try covering it and popping in the fridge for a bit to see if that helps at all. Let me know how they turn out! xT

  3. I tried making these yesterday and the dough was super sticky. I added more flour but I think I added too much. I ended making just 8 of the 30 cookies and they turned out delicious. Better that I didn’t make so many because I would have ate them all. I put the rest of the dough in the freezer as the question was not yet answered on whether the dough could be in the freezer. How long can I store the dough in the freezer? Thank you for the recipe!

  4. Hey Tieghan!

    Can this dough be frozen overnight or is it best just to do it all in one day? I am planning on making them for a treat this weekend. 🙂

    1. Hi! I have the same question as another person about storing the dough overnight. Can the dough be refrigerated overnight? Or do you recommend still freezing if waiting until the following day to bake? Thanks!

    2. Hey Hannah,
      You could make the dough overnight and just keep in the fridge:) I hope this recipe turns out well for you, please let me know if you give it a try! xT

  5. Hi Tieghan! I’m about to attempt this recipe and was wondering, why 4 cups of flour? I’m worried it might be too much flour and dry out the cookie? Appreciate any advice you have, this are very cute and I can’t wait to make them!

    1. Hi Norah,
      I’ve never had any issues with the amount of flour, the recipe makes a lot of cookies:) Let me know how they turn out, I hope you love them! 🎃

  6. 5 stars
    These cookies are my absolute favorites. I’ve been making them for a few years now. Thank you for this great recipe. They taste like fall and all things I love.

    1. Hi Kerstin,
      Happy Monday!! 👻 I am so glad this recipe was tasty for you, thanks a lot for trying it out! xT

  7. 4 stars
    I was able to make 28 cookies (14 sandwiches) plus little scraps. On their own without the cinnamon sugar or chocolate, they’re rather dry, but with the topping and filling they come together nicely! We made a few not as sandwiches, but a single cookie coated in cinnamon sugar and drizzled with chocolate for the younger kiddos. Yum!

    1. Hey Heather,
      Wonderful!! I am thrilled to hear that this recipe was enjoyed and truly appreciate you making it! Have a great weekend! 🍁🍂

  8. Hello,
    Planning to make these for a Halloween party this weekend and I’m sure they’ll be a hit! One question- did you put all 3 sticks of butter in the batter? Or is any of that reserved for the later melting/brushing of the baked cookie?
    Thank you!

    1. Hey Samantha,
      You are going to use all 3 sticks in the dough and then just use a couple tablespoons for the brushing. I hope this recipe turns out amazing for you! xT

  9. 1 star
    Mine were an epic fail. I don’t know what I did wrong, but something! I bought the cookie cutters but the dough just got stuck in them.

    Oh well, the granddaughters will never know.

    1. Hi Lisa,
      Thanks for trying the recipe, so sorry to hear you had some issues. Was there anything you adjusted in the recipe? Sounds like you may have needed some more flour or to chill the dough. Please let me know if I can help in anyway! xT