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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: 178 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. 

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

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Comments

  1. I was able to find and order the cookie cutters from a seller on Etsy! I’m excited to try this recipe with my daughter when they arrive.

  2. Hi! Iam going to try this recipe tomorrow. I’ve never baked cookies like these before, so Iam very excited for it! We do’nt have Halloween in my country, so I quess it would be just for a little Friday treat. 🙂

  3. I’m going to try this recipe this weekend, so excited! Question, can you freeze the dough and bake at another time?

    1. Hey Lisa,
      Sure, that would be just fine to do! I hope you love the recipe, please let me know how it turns out! xTieghan

    1. Hey Chelsea,
      The recipe will make 15 sandwiches. I hope you love the cookies, please let me know how it turns out! xTieghan

    1. Hey Carol,
      Yes, that should work well for you. I hope you love this recipe, please let me know if you give it a try! xTieghan

  4. 5 stars
    Made them last Halloween and they were a big hit with all the family! So delicious, just making a batch now as a sweet treat for the weekend. Can I freeze the dough to make more another time? If so how long would you recommend keeping it in the freezer before using? Thanks 🙂🎃

    1. Hey Olivia,
      Awesome! It is so great to hear that this recipe was enjoyed, thanks a lot for giving it a go! I would freeze for no more than 3 months. xTieghan

  5. Hi, made these cookies and they were delicious. Do you think I can use the dough recipe to make gingerbread houses? My kids don’t like the gingerbread flavor

    1. Hey Neomi,
      Thanks so much for giving the recipe a try! Sorry I have never used this dough for gingerbread houses so I am honestly not sure how that will work out. Please let me know if you have any other questions! xTieghan

  6. 4 stars
    Perfectly amazing texture and held shape perfectly too. The taste was very mild but still craveable. I felt like it was a bit bland (tasted only a hint of the spice) and am wondering if I could add the something I felt missing… but beautiful texture and great fun to make!

  7. 5 stars
    Love these so much ! I’m also freezing some cookies after baked so they are ready to just add the chocolate to before Thanksgiving.. thank you Teagan 🙂

  8. Do you divide the butter? The recipe calls for you to brown butter at the end, but the first step is to cream all the butter.

    1. Hey Midge,
      The butter that I am referring to in step 4 is for the cinnamon sugar coating. I hope you love the recipe, please let me know if you have any other questions! xTieghan

  9. These are so cute so I figured I would give them a try But the dough was super crumbly and was really hard to transfer to the baking sheet without falling apart. Do you have any tips for keeping the dough a bit more solidified? Thank you!!

    1. Hey Lindsay,
      So sorry you had issues with the dough? Did you happen to adjust the recipe at all? Different cooking method? These would help me to better answer your question! xTieghan

  10. 5 stars
    OMG TIEGHAN
    Thank you
    these are literally amazing. I’m blown away at this cookie I’ve just created. The sugar cookie is so buttery and crisp and then the browned butter/cinnamon sugar top tastes so good. Then the milk choc stuffed inside?!? I’m in love and they are actually so adorable. I’m making these for a local Halloween treat bake-off! I hope I place.

    1. Aw you are so kind!! I am really glad these cookies turned out so well for you and hopefully you win the bake-off!! Thank you! xTieghan

  11. Hi, these looked super cute and fun to make but not at fun as expected… they took much longer than expected. Amazing idea and all, but I was wondering how i could make the cookies thinner without burning them (minus the freezing – sorry!). Thanks so much, Holly

    1. Hey Holly,
      Thanks for giving the recipe a try! To make them thinner, you would just roll thinner. I hope you love the recipe, please let me know if you have any other questions! xTieghan

    1. Hey Nat,
      Yes that would be fine! I hope you love the recipe, please let me know if you have any other questions! xTieghan

  12. 5 stars
    I just wanted to say how much I love your recipes!! I made these cookies today with my 3 year old, we filled them with Nutella and let me just say how amazing they turned out!! Mine were definitely not as cute as yours but they sure tasted great!! Thanks for all the wonderful recipes!! Keep them coming!! Xoxoxo

    1. Thank you so much Sarah Jane!! I am so happy you have been loving my recipes and I hope you continue to! xTieghan

    1. Hi Carolyn,
      The 1.5 cups of butter is being used in the cookie batter. The butter you are browning in step 4 is 2 tablespoons of butter for the cinnamon sugar coating. I hope you love the recipe, please let me know if you have any other questions! xTieghan

    1. Hey Sara,
      Yes totally fine! I hope you love the recipe, please let me know if I can help in any other way! xTieghan

  13. 1 star
    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

    1. 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

  14. 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.

    1. 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

    1. 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

    1. 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

  15. 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.

    1. 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

  16. 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!

    1. Hi Isabel! I spoon and level a cup measurement! I hope this helps! Please let me know if you have any other questions! xTieghan

  17. 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

    1. Hey Andrea,
      Yes that would work. I hope you love the recipe, please let me know if you have any other questions! xTieghan

  18. 5 stars
    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.

  19. 5 stars
    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!!

  20. 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!

    1. 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 ??

  21. 5 stars
    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?

    1. 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 ???

    1. 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 ???

  22. 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?

    1. 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 ???

    1. 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.

  23. 5 stars
    These look delicious. Could you re-share the exact cookie cutter link? I’m getting a different product. Love all your recipes!

  24. 5 stars
    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.

  25. 5 stars
    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 🙂

  26. 5 stars
    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 😉

    1. 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!

  27. 4 stars
    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.

    1. 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!

  28. 5 stars
    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.

    1. 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

    1. 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

  29. 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?

    1. 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

  30. 5 stars
    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.

  31. I’m a bit confused. Are you putting the cookies right in the oven after freezing or waiting until they’re soft again?

    1. 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

  32. 5 stars
    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!

  33. 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.

    1. 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

  34. 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!

  35. 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.

  36. 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!

    1. 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!

  37. 5 stars
    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.

  38. 5 stars
    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.

  39. 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?

    1. 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

  40. 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!