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! 🎃
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? 😄
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.
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. 😅
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.
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!
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!