Jack-O’-Lantern Sandwich Cookies are a festive and fun Halloween treat that combines buttery, tender cookies with a sweet, creamy filling. Shaped like classic carved pumpkins, these cookies bring all the charm of jack-o’-lanterns to your dessert table. Perfect for parties, gifting, or a spooky baking day at home, they’re as delightful to make as they are to eat.
These cookies start with a soft, buttery dough that’s easy to roll out and cut into pumpkin shapes. Half of the cookies have jack-o’-lantern faces cut out to create the signature look, while the other half remain solid to hold the filling. The faces can be simple triangles for eyes and a smile, or you can get creative with spooky, silly, or surprised expressions.
Once baked to a light golden color, the cookies are sandwiched together with a filling that’s sweet and creamy. Popular choices include vanilla buttercream, orange-tinted frosting, cream cheese filling, or even a smooth layer of chocolate or jam for a fun flavor twist. The filling peeks through the jack-o’-lantern faces, adding both color and a playful touch to every bite.
Decorating is where the real fun happens. You can tint the cookie dough orange using food coloring or leave it natural for a classic look. A dusting of powdered sugar or a drizzle of icing can add extra flair. These cookies look great arranged on a party platter, wrapped up as Halloween favors, or served alongside other festive treats like cupcakes and candies.
Not only are Jack-O’-Lantern Sandwich Cookies adorable, but they’re also delicious. The buttery, melt-in-your-mouth cookies pair perfectly with the creamy filling, making them irresistible to both kids and adults. They offer the perfect combination of festive fun and homemade charm, turning a simple cookie into a Halloween centerpiece.
Ingredients
- 1 cup unsalted butter softened
- 1 cup granulated sugar
- 1 teaspoon vanilla extract
- 1 large egg
- 2 3/4 cups all-purpose flour plus more for dusting
- 1/2 teaspoon baking powder
- 1/2 teaspoon salt
- 1/2 cup cream cheese softened
- 2 cups powdered sugar
- Orange food coloring
- 1 teaspoon milk
Instructions
- Preheat the oven to 350°F (175°C). Line baking sheets with parchment paper.
- In a large bowl, cream together the butter and sugar until light and fluffy.
- Mix in the vanilla extract and egg until well combined.
- Gradually add flour, baking powder, and salt, mixing until a dough forms.
- Roll out the dough on a lightly floured surface, about 1/4 inch thick.
- Cut out cookies using a pumpkin-shaped cookie cutter. Use a knife to carve Jack-O’-Lantern faces into half of the cookies.
- Place cookies on prepared baking sheets and bake for 8-10 minutes or until edges are lightly golden. Cool completely.
- To make the filling, beat the cream cheese until smooth, then gradually add powdered sugar until combined.
- Mix in a few drops of orange food coloring and milk until desired consistency and color are reached.
- Spread the filling on the flat side of each non-carved cookie. Top with a carved cookie to create a sandwich.
I dunno, cookies with faces on ’em? Seems weird to me. But hey, each to their own! 🤷♂️
I actually think they’re super cute! The kids will love them. 😍
I tried this recipe but forgot the milk in the filling. Still tasted ok but not so pretty.
These are super cute! My kids loved making them. We had a blast! 🎃
My dough felt dry after mixing in the flour—like it wouldn’t really come together. I had to add a splash of milk to get it workable. After that, they baked up fine. Maybe I measured wrong, but yeah.
Just ok. My filling was too runny. 🤮
Oh no! Sounds like the filling might have been too runny because the cream cheese wasn’t beaten enough or the powdered sugar wasn’t added slowly. I’m sure you can fix it next time!
Eww, that does sound gross! But have you tried chilling the filling before using it? It might help. 🤷♂️
I don’t get why you need food coloring. Can’t they just be regular color? 🤔
Tastes great, but my cookies didn’t look anything like the picture. More practice needed, I guess!
These cookies are adorable and taste amazing! My kids loved helping with the faces. Will make again for Halloween!
These taste okay, but I expected more pumpkin flavor. What’s the point of pumpkin cookies if you don’t use real pumpkin?
I totally get you! Real pumpkin would definitely enhance the flavor. I’ve tried recipes with actual pumpkin, and they’re way better. Next time, maybe add some canned pumpkin puree?
Who needs real pumpkin? These cookies are sweet enough as is! Plus, pumpkin spice is the important part, right? Just enjoy them!
These were SUCH a fun Halloween project. The pumpkin cutter plus the faces made them look way more impressive than my actual carving skills 😅 The filling tasted like sweet cream cheese icing—would definitely make again.
THese r the best!! I made them last year. Everyone loved them. Will do it again for sure!
In the instructions, it says to carve faces. Do you carve pumpkins too? Lol.
Yum! Just made a batch, and they’re the best cookies ever! 🥳
These cookies are adorable! My kids loved making them for Halloween. Will definitely make again! 🎃
I’m so glad to hear that! These cookies are super fun to make, especially with kids. 🎃🍪
Easy to follow! Just made these for our Halloween party. They turned out perfect! 🎃
Yum yum yum! Will be making these every year! 👏🧡
I don’t get why you need orange food coloring. I mean, cookies are supposed to be brown, right?
Yummy! Would love to try these with chocolate filling next time!
I used chocolate chip instead of cream cheese. Still yummy! 😋
Chocolate chips? That’s different! But I bet it still tastes great. Who needs cream cheese anyway?
idk if I like orange in cookies, seems weird. lol.
Why do they call them Jack-O’-Lanterns? They don’t even have eyes! 🤔
Haha, right? Maybe they should call them Jack-O’-Biscuit! 😄
I think they call them that because of the lanterns in Halloween lore. It’s just an old tradition! But yeah, no actual eyes! 🤷♀️
Too much butter, I think. The cookies were greasy. Next time, I will lessen the butter, maybe?
I totally get it! Butter can be tricky. I usually just use a bit less too. It helps a lot!
Nah, it’s fine! A little grease just means they’re richer! More butter, more flavor, right? 😄
I don’t get why there’s both baking powder and a pretty short bake time—mine were kind of dry. Next time I’ll pull them earlier.
I’ve had the same issue with shorter bakes—9 minutes sounds right but my oven runs hot. I’d pull them the second the edges look set, not golden-brown.
So cute! But I think real pumpkins are better for carving than cookies.
Aint nobody got time for this! Just buy cookies at the store.
Great recipe! But I added chocolate chips too, just because. It turned out super delicious!
Too sweet for my taste, but they look festive. Not my fave.
I followed it pretty closely, but my cookies spread a bit more than I expected. Still tasted great though—vanilla + cream cheese combo is a win. Next time I’ll chill the dough before rolling.
Good recipe, but why does everyone insist on using butter? Margarine is just as good!
This recipe is fab! I made them for my kids and they loved it!
That’s awesome! I’m glad your kids loved them! They look so cute!
Is it really necessary to use cream cheese? Can’t I just use regular frosting?
Tasted great but my cookies flattened out. What did I do wrong? 😩
10/10 would recommend to anyone who loves cookies!
I can’t believe how good these turned out! My kids loved making them, too!
These cookies make me think too much of Halloween! I’m not ready yet. 😅
Not gonna lie, the carving part was chaos for me 😅 The faces came out more “random jack-o-lantern” than detailed. But the sandwich cookies were still delicious, so I’m keeping the recipe.
Cute idea, but the dough was kinda sticky for me. I had to keep adding flour while rolling, otherwise the cutter stuck. Still worth it for Halloween parties!
Yum! My kids were super excited for these. Thanks for sharing!
I followed the recipe, but the dough was way too sticky. What did I do wrong?
Honestly? Cute idea but the “sandwich” part made them fall apart when I tried to assemble. Maybe I waited too long after baking? Still ate them anyway lol.
Aw man, I’m sorry! I’ve noticed if the cookies aren’t *fully* cool, the filling makes them a little slick and they crack when you try to press them together. Did you cool completely like 100% cool?
Same thing happened to me 😅 I waited like 10 mins and then tried assembling… rookie mistake. Next time I cooled on a rack longer and they held up way better.
I’m skeptical about baking powder with sandwich cookies—mine had a weird little puffiness. Still decent, but I’d try fewer baked minutes next time.
Not sure about using powdered sugar + food coloring + milk—mine was grainy until I kept beating longer. Once it smoothed out, it was fine.
Totally agree—mine got grainy too at first. I was impatient and didn’t beat long enough. After another minute or two it smoothed out and tasted great.
Hmm, I might try a different approach next time. I used fewer drops of food coloring and only a tiny splash of milk, but I still felt like it turned a little thick/gritty. Did you sift the powdered sugar?
These are sooo cute! Perfect for Halloween. My kids loved them!
OMG these are so cute I almost don’t want to eat them. The filling ratio (cream cheese + powdered sugar) is spot on—easy to pipe/spread and not too sweet.
Made these with my kids, they had so much fun! Sweet and spooky! 🎃
That sounds like a blast! I can’t wait to try this with my kids too! 🎉
I messed up and used baking soda instead of powder, and they turned out flat. Who knew? Lol. Still tasted good tho.
These cookies are adorable! My kids loved helping to carve the faces. Will definitely make again!
These cookies were a hit at the Halloween party! Everyone loved them!
Isn’t cream cheese kinda weird for a cookie? I think I’ll skip it.
I actually think cream cheese adds a nice creaminess! Give it a try. You might be surprised!
Nah, I can’t see how cream cheese belongs in cookies. Sounds more like a cheesecake filling instead of a cookie!
I don’t know about baking, but my sister said they look proffesh! 😂
These cookies are sooo cute! Perfect for Halloween. 🎃
Easy to follow and turned out delicious, but mine didn’t look as pretty as the pictures.
Don’t worry about the looks! Taste is what counts. I’m sure they were still yummy!
Never thought I’d make cookies from scratch, but this recipe was easy enough! Tastes great too!
So tasty and not too sweet! I added some chocolate chips, made them even better. YUM!
I had a hard time getting the dough right. It was sticky and I ended up adding more flour. But they looked cute in the end.
These are super cute! I made them for a Halloween party and they vanished fast. The orange filling really makes the faces pop.
Aww love that! “Vanished fast” is the best compliment—those orange faces must look so fun on a Halloween table 😄🎃
Loved it! Gonna make again! Perfect for my lil’ goblins ❤️
They taste good but took me forever to get the dough right. Maybe I added too much flour?
I had the same issue with the dough! Maybe try adding the flour slowly next time. It’s such an awesome recipe, though!
Easy and fun! Perfect for Halloween. Will make again for sure!
I tried making these but mine fell apart. I don’t think I did it right. 🙁
Works great if you don’t overbake. Mine held together and the sandwich part didn’t squish. Will make again—simple enough.
These were surprisingly easy for “holiday-looking” cookies. My only tweak: I chill the dough 20 min before rolling so it doesn’t get sticky.
Totally agree—8–10 min is the sweet spot. I overbaked mine once and they got crumbly, but when I pulled them early the faces stayed crisp.
I found the dough too sticky, need to add more flour next time.
Ugh, these were a disaster. Overcooked in 8 min, so disappointed. 😞
Not good, tastes weird. I expected more pumpkin flavor.
5 stars for the creativity! But can anyone tell me why I need orange food coloring? 🤔
The orange food coloring is just for the color! It makes the filling more festive for Halloween! 🎃
Not sure why mine spread. I used 1/4 inch thickness like the instructions say, but the pumpkin cutter details blurred. Flavor is good, presentation… kinda haunted.
This recipe is great but the instructions are a bit confusing. I messed up the filling part.
350°F seems right, but my cookies browned fast on the edges. I’d check earlier—like at 7 minutes—especially if your oven runs hot. Also, parchment helped a lot so they didn’t stick.
I followed it exactly, but my dough was super sticky even with extra flour. I had to wrestle it a lot and the faces lost some detail. Still tasty though—just not as neat.
Wow! These turned out amazing! 👻
Not as good as I thought. The filling needed more flavor. 😕
5/5 cookie cutter dream. 🎃
Right?! These look like the exact kind of cute pumpkin project I wish I could pull off every year. 🎃
Pretty straightforward recipe. I chilled the dough for 30 minutes before rolling, and it made cutting so much easier. Also, 8 minutes was perfect in my oven (10 made the edges slightly too dark).
I tried this but my dough felt super sticky, even after chilling. I ended up using extra flour and it still kinda spread. What thickness do you aim for after rolling?
Chilling the dough is the move! I did 20 minutes and mine cut way cleaner too. Love the note about 8 minutes—I’m always worried about overbaking.
I followed the recipe exactly, but something went wrong. My dough was too sticky. 🤷♀️
The taste was good, but my cookies spread too much and didn’t hold the shape. What did I do wrong?
Too much work for me! I just want to eat cookies, not play arts & crafts! 😩
Not gonna lie, cutting the faces was harder than the recipe makes it sound. I ended up keeping it simple—just carved eyes and a grin—and they still looked cute. Cookies were tasty though, just take your time.
I tried making these but my dough was too sticky. What did I do wrong?
didnt turn out right. maybe I did it wrong
I used pumpkin spice instead of vanilla and they were a hit! 😊 Definitely making again!
These cookies were a hit at our Halloween party! Super cute and delicious!
Can you use margarine instead of butter? I’m outta butter… 😩
Yeah, you can use margarine! It might change the flavor a bit, but it should work fine! Good luck! 😊
These turned out super cute! The pumpkin faces looked exactly like a jack-o’-lantern, and the cream cheese filling tastes way better than I expected. I did bake them 9 minutes for perfect golden edges.
I made these too and totally agree—mine also needed a little less time than the recipe says. 9 minutes worked great for the golden edges.
Ahh love this! The jack-o’-lantern faces are the best part—so glad the cream cheese filling surprised you (in a good way). 🍪🎃
Tried to make these with my grandma but she forgot the milk. Still turned out fun though! 😂
These came out adorable! The orange filling tastes like a mellow cream cheese frosting, and the texture is spot on. My kids actually fought over who got the “spookiest” one 😂
Nailed it! Perfect for Halloween. Everyone was impressed and they disappeared so fast!
Meh. I expected more flavor, that’s a lot of sugar for not so much taste.
I followed everything, but my cookies spread more than I expected and the details got a bit fuzzy. Still tasty though—just not as “Jack-o-lantern” as the photos.
Pretty easy, but I had to bake closer to 10–11 minutes for them to set. The filling tasted great though—orange color was perfect.
Same here! Mine looked done at 8 minutes but weren’t really set—10–11 minutes fixed it. Love that orange was spot-on too!
Hmm I followed the 8–10 minutes exactly and they came out a bit dry 😕. Maybe my oven runs hot? Either way the filling flavor is legit.
Not bad. I used less orange coloring and it was more like orange cream cheese blobs lol. Would make again.
Omg orange cream cheese blobs sounds hilarious 😂 but honestly that’s probably even tastier than the “perfect” look. Love that you’d make them again!
I made these last year and mine also turned kind of blob-y if I went light on coloring. Next time I’ll try your approach—less is more maybe?
I tried this but they came out super flat. What did I do wrong? 🤨
The cookie dough was a little crumbly at first, but after a quick extra mix it came together. Carving the faces is honestly the best part.
Totally agree—the face carving is the fun part 😂 My dough was crumbly too at first but a little extra mixing fixed it!
Super cute! My kids loved helping me cut the faces. Can I use chocolate instead of cream cheese?
Mine spread a little and some faces blurred. I think my butter was too soft and I didn’t chill the dough. Still tasted good!
The amount of flour feels like it might vary. I needed closer to the 2 3/4 cups? Maybe my butter was softer than usual. Dough came together eventually, but I was nervous at first.
350°F for only 8-10 min seems too short—mine were pale and soft in the middle. Flavor was okay, but I think the cookie thickness needs adjusting. Also I ran out of powdered sugar so I used regular sugar (bad idea).
Really yummy😋😋! The cream cheese filling is the best part! Makin these again for sure!
These cookies are adorable! They were a big hit at our Halloween party! 🎃
I’m so glad to hear that! They look so fun! 🎉 What did you decorate them with?
I made these too, but they didn’t turn out as cute. 🤷♀️ Mine were just blobs!
I don’t understand why you need to roll out the dough. Can’t just scoop it out right? Seems easier.
These came out adorable—my kids LOVED the faces. I dusted a bit extra flour like it said and the cutouts stayed sharp.
I don’t get why people are so excited about these cookies. They’re just cookies. 🙄
They’re not just cookies; they’re festive! Halloween is a big deal for many, and this recipe brings that spirit to life. 🎃
I think cookies are just cookies, but maybe people like the idea of spooky shapes? Still not convinced they are worth all the hype.
I think 2 cups of powdered sugar is way too much for the filling. Mine got super thick and almost gritty. Next time I’ll reduce it or add more cream cheese/milk to balance. Otherwise flavor was okay.
Too much butter and sugar. I feel like I’m going to explode! 😩
I think my oven runs hot because mine browned fast at like 6-7 minutes. Also the carving step took longer than I thought—my pumpkins looked more like angry blobs 😅
Yeah that browned fast at 6–7 min usually means the oven runs hotter or the rack’s too close to the heating element. I’ve done the same thing—burnt cookies before the “edges lightly golden” part 😂
Nice recipe but what’s the point of the food coloring? Can’t we just use real pumpkins??
I followed it exactly but the dough was crumbly. Maybe I used a smaller egg? I added a tiny splash more milk and it turned around. Would make again.
I’m glad it turned around for you! Crumbly dough can happen if the flour is a bit packed or the egg is on the smaller side—adding that tiny milk splash is exactly what I do too.
These are so cute! I made them for my kids and they loved them!
Not gonna lie, the filling came out too sweet when I followed it exactly. Next time I’ll cut back on powdered sugar or add a tiny pinch of salt. Cookies themselves were buttery though.
Turned out pretty good, but my dough felt a little dry before I baked it. I added a tiny splash more milk when shaping and it came together nicely. Baking time was perfect at about 9 minutes for me.
Quick question: can you use gel food coloring instead of drops? I used like 10 drops and it was WAY too bright orange, lol. Taste was fine just intense.
These are adorable! The pumpkin shape really sells the Halloween vibe, and the cream cheese filling is perfectly sweet without tasting too heavy. I used a little extra orange coloring and they looked super fun on the tray.