Chocolate Chess Oreo Pie Recipe (2024)

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Cookies and Chess Pie are a match made in heaven!! You’ll love this decadent Oreo version with a rich chocolate chess filling and buttery Pillsbury pie crust! And you’ll never believe what the secret ingredient is…

I participated in a campaign on behalf of Mom Central Consulting for Heinz Vinegar. I received a product sample to facilitate my review and as a thank you for participating.

My interest in dessert (beyond stuffing it in my face whenever possible) began with Food Network. Anyone else?

When some of their night-time shows (which, I think we can all agree, are generally “cooler” than their daytime cooking shows… no disrespect, of course. I love you Alton!) started gaining a little more attention, it finally dawned on me that I might like food more than just for eating. Like… maybe I wanted to make a career out of it.

Anyway. Short story: Chris and I become obsessed with nighttime food TV.

One of our favorite shows on Food Network was, “The Best Thing I Ever Ate.” They interview celebrity foodies who share with us their favorite places to eat within a specific genre (favorite fried foods, favorite ice cream, favorite food truck food, etc…). One of the foods mentioned on this show was the Baltimore Bomb Pie, created by Dangerously Delicious Pies in Baltimore, MD (which I recently visited for the first time!!)

And it was hearing about this Baltimore Bomb Pie that first introduced me to Chess Pies. I don’t know about the rest of you, but that’s the first time I had ever heard the word “chess” in a food context, and I was thoroughly intrigued. A pie filling that calls for vinegar??? Super weird.

But, you know me. I don’t really ask many questions when it comes to sugar. Point me in the right direction, and I’m there, fork in hand. So I attempted my own version of Baltimore Bomb Pie and made (and ate!) my very first chess filled pie, vinegar and all.

I loved every, delicious moment of it.

I think the best way to describe a chess pie to someone who has never eaten one is to say that it’s a little bit like a pecan pie. Only not quite so squishy. And without the pecans.

In fact, my favorite chess pies are filled with cookie pieces. I loved this Pumpkin Cookie variation from last fall!

So when an opportunity came along to work with Heinz Apple Cider Vinegar, it seemed like a perfect opportunity to create a new variation on my favorite vinegar-including dessert. Don’t let the vinegar scare you! It adds just a teeny-tiny-bit of tang to the chocolate that is really, really delicious.

And it turns out that Oreos make for an incredible chocolate chess pie. Although, was there really any doubt?

I love my pies a la mode. And if you’re an ice-cream-sundae addict like me, whip up a batch of this homemade chocolate syrup to pour on top as well!

You can eat this pie warm, of course. But I think it’s really best the next day once it’s set up really well. And, for some reason, I actually like the flavor a little better at room temperature too!

Chocolate Chess Oreo Pie

Ingredients

• 24 Oreos (1 1/2 sleeves from a standard sized package), crumbled
• 1 unbaked Pillsbury pie crust
• 1 stick unsalted butter, melted
• 3 tbsp. cocoa powder
• 1 cup sugar
• 2 eggs
• 1 1/2 tablespoons Heinz Apple Cider Vinegar
• 1 teaspoon vanilla extract
• 1/4 teaspoon kosher salt
• 1/2 cup semi-sweet chocolate chips

Instructions

1. Preheat oven to 350 degrees F.
2. Press the pie crust into the pan. Fill the pie crust with the crumbled Oreos. Set aside.
3. Whisk together the melted butter, cocoa powder, sugar, eggs, vinegar, vanilla extract, and salt.
4. Pour the filling over the Oreo crumbles. Use a spatula to spread the filling evenly over the Oreos, and then to gently mix so that the filling is mixed in with the cookie pieces. Sprinkle chocolate chips over top.
5. Bake for 35-45 minutes, until the pie appears set in the middle.
6. Let cool for at least 20 minutes before cutting and serving.
7. Serves 8

I participated in a campaign on behalf of Mom Central Consulting for Heinz Vinegar. I received a product sample to facilitate my review and as a thank you for participating.

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