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Chocolate Peanut Butter Stuffed Jack-O’-Lantern Cookies. Sweet and creamy peanutty buttercream, sandwiched between two chocolate sugar cookies and dipped into milk chocolate. They taste like a peanut butter cup, but in cookie form. Yep, there’s nothing not to love about these cookies. And to top it all off…they’re the easiest to make. Just as perfect for Halloween night as they are after an elegant Thanksgiving dinner. But maybe best when you’re simply in need of a deliciously sweet peanut butter filled chocolate cookie!

overhead photo of Peanut Butter Stuffed Chocolate Jack-O’-Lantern Cookies on serving trey

Ending the week on a very sweet (and very cute) note with these chocolate Jack-O’-Lantern cookies.

I love these cookies so much. Sometimes I make recipes and they just don’t turn out. Sometimes I remake them and can get them to work. Then, sometimes I have recipes like today that originally were something completely different. But over the course of two weeks turned into an entirely new recipe. That is this recipe, and it’s probably my favorite of the month.

Because I mean, are these cookies not the cutest?! And what could be better than a chocolate cookie stuffed with peanut butter?! Especially one that’s covered in milk chocolate and a pinch of flaky sea salt too.

Nothing is better. Your weekend needs these cookies. Trust me.

overhead photo of Chocolate Jack-O’-Lantern Cookies before baking

The Cookies.

Start with the cookies themselves, which are essentially a chocolate sugar cookie. Similar to an Oreo cookie, but so much better…because these cookies actually have delicious chocolate flavor. The secret is to use dark chocolate cocoa powder instead of regular cocoa powder. Not only does the dark cocoa add a rich chocolate flavor. It also gives the cookies a pretty color that doesn’t fade away once the cookies bake.

The best part about these chocolate sugar cookies? They are so simple to make and so forgiving. I’m talking simple. Think beating butter with sugar, adding an egg, adding the dry ingredients, rolling, cutting, and baking. There is absolutely nothing fancy or complicated about these cookies.

Whenever I make any kind of cut out cookie, I always like to roll the dough out, cut the cookies, and then freeze the cut cookies on a baking sheet for a few minutes. This ensures the cookies hold their shape. AND I don’t have to wait for the dough to chill. It’s the easiest.

To cut my cookies, I used these pumpkin cookie cutters, but also made some circle cookies stamped with cute pumpkins. I preferred the pumpkin cookie versus the stamps, but if you want to go the stamp route, I recommend these cute ones.

Chocolate Jack-O’-Lantern Cookies on baking sheet before baking

The Peanut Butter Filling…

While the cookies are baking, make the filling…a simple mix of peanut butter, butter, sugar, and vanilla.

It’s creamy, salty, perfectly sweet, and tastes just like the inside of a peanut butter cup.

So addicting.

overhead photo of Peanut Butter Stuffed Chocolate Jack-O’-Lantern Cookies on serving trey

And on to assembling…

Here’s the deal. I’ve said this many times, but I am by no means a professional when it comes to decorating cookies. Early on in my baking “experiments” I tried so hard to create perfectly decorated cookies with what I’ve found to be, pretty flavorless icing. I was never happy with my creations. In fact, most times my efforts ended in tears. So instead of trying to create perfect-looking cookies, I focused on creating cookies that actually taste GOOD. Meaning no weird colored frostings, no overly sugared candies, and no food dies.

Just not my thing.

But decorating with melted chocolate? Yes, yes. That I can…and will…do!

For these cookies, I simply dipped half the cookie into melted milk chocolate. Then I drew on little lines of chocolate as additional decoration. To draw the chocolate on the cookies I used a small ziplock bag with melted chocolate inside. I then cut a tiny portion of the corner off of the bag off. This is my go-to trick for drizzling chocolate.

Finish each cookie with a sprinkle of flaky sea salt. If you wanted to add a little festive pop of orange color, sprinkles would work too!

side angle photo of Peanut Butter Stuffed Chocolate Jack-O’-Lantern Cookies stacked on top of each other

Not only are these cookies insanely delicious. They’re also just a fun, festive, and truly easy cookie that EVERYONE can make.

Meaning…great for kids, but fun for adults too.

I’m looking forward to recreating these for my family’s Thanksgiving, as I know they’ll be a huge hit.

Because again, chocolate and peanut butter. Best combo ever!

Looking for another Halloween cookie option? Try theses Milk Chocolate Stuffed Jack-O’-Lantern Cookies from last year!

overhead close up photo of Peanut Butter Stuffed Chocolate Jack-O’-Lantern Cookies on serving trey

If you make these Peanut Butter Stuffed Chocolate Jack-O’-Lantern Cookies, 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 tag me on Instagram! Looking through the photos of recipes you all have made is my favorite!

Peanut Butter Stuffed Chocolate Jack-O’-Lantern Cookies

Prep Time 30 minutes
Cook Time 15 minutes
Total Time 45 minutes
Servings: 12
Calories Per Serving: 1174 kcal

Nutritional information is only an estimate. The accuracy of the nutritional information for any recipe on this site is not guaranteed.


Peanut Butter Filling


  • 1. Preheat oven to 350 degrees. In a large mixing bowl, cream together the butter, sugar, and vanilla until light and fluffy, about 3-5 minutes. Add the egg and mix until evenly combined. Add the flour, 1/2 cup cocoa powder, baking soda, and salt, beat until combined and the dough forms a ball. If your dough feels too wet to roll out, add the additional 2 tablespoons cocoa powder.
    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 or pumpkin cookie stamp. Carefully transfer the cookies to a parchment-lined baking sheet. Cover the baking sheet and place the sheet in the freezer, freeze until firm, about 10 minutes. Roll out the leftover scraps, and repeat with the remaining disk of dough.
    3. Bake the cookies for 10-12 minutes. Cool on the baking sheet five minutes and then transfer to a wire cooling rack to cool completely.
    4. To make the filling. Add the peanut butter, butter, powdered sugar, and vanilla to the bowl of a stand mixer. Beat until light and fluffy.
    5. Dip half of the cookies, stem side down, into melted chocolate to coat about 1/3 of the top (see photos). Decorate as desired with additional melted chocolate. Sprinkle with sea salt. Chill the cookies in the freezer for 10 minutes. Spread the peanut butter filling over the cookie halves with no chocolate. Place the top cookie, chocolate side up over the peanut butter, gently pressing to adhere. Cookies can be served immediately or stored in an airtight container for up to 3 days. 


Pumpkin Cookie Cutter
Pumpkin Cookie Stamp
To Make Gluten Free: Use an equal amount of your favorite gluten free flour blend in place of the all-purpose flour. I recommend Cup4Cup gluten free flour
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  1. 5 stars
    This is the recipe I will be using from now on for chocolate sugar cookies. They turned out so yummy! I baked them for five mins, then let them rest for another five mins on the cookie sheet before putting them on the wire rack. So soft and yummy. They would be excellent for a soft Oreo dupe recipe!

    1. Hey Doja,
      I truly appreciate you making this recipe and sharing your feedback, so glad to hear it turned out well for you! xx

    1. Hi Fiona,
      Wonderful! I really appreciate you giving this recipe a try, I love to hear that it was enjoyed!! xTieghan