Peanut Butter Stuffed Chocolate Jack-O’-Lantern Cookies.

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!

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.

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.

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.

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!

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!

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!