Oreo Dirt Box Cake Cups

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Oreo Dirt Box Cake is a recipe that I first made about 20 years ago for Thanksgiving. I saw it in a magazine and thought “Oh that looks fun”. And so it began – dirt box cake for Thanksgiving. I know silly right. But honestly some people do not like pumpkin pie and almost everyone loves Oreos. The first year I made it I went to Walmart and purchased a small plastic flower container. I took the container home and cleaned it really well. I made the dirt box cake and put it in the flower box. I purchased a few real silk flowers and put them in the cake and added some gummy worms. I know cheesy right. I walked into Nanny’s house (my husband’s grandmother) and placed the flower box on the dessert table. Can I tell you that my family members looked at me like I had lost my mind. That was until dessert time and I told them it was actually a dessert. After that – game on. There was not one single bite of the cake left.

This Oreo Dirt Box cake is traditionally a Thanksgiving dessert for our family but this year I decided to make them with a couple of my grandsons for Halloween. Due to Covid (hello 2020), I decided to make them in little cups for individual servings. Better yet these little cups had lids (thank you Walmart) so I was able to pop the lid on and put straight in the fridge. The boys had a blast and I am sure we will be making them for Thanksgiving with little pumpkins.

I have made them at Easter with marshmallow peeps (my favorite), at Christmas with candy canes and so many other holidays. This is a recipe to have fun with and let the kids in on the fun. I can promise you the kids will not remember what they ate for Thanksgiving from year to year but they will remember the time they spend with you in the kitchen making memories.

Quick Tip: Don’t you hate when you go to make a recipe and you realize you are out of powdered sugar. Well there is a way you can make your own. Click on this link for instructions: making homemade powdered sugar.

Oreo Dirt Box Cake Cups

Recipe by Cooking with Aunt PamCourse: DessertCuisine: AmericanDifficulty: Easy


Prep time




  • 2 (3.4 oz) packages Jello instant French vanilla pudding

  • 2 cups whole milk

  • 1 package Double Stuff Oreo cookies

  • 16 ounce container of Cool Whip (thawed)

  • 8 ounce package of cream cheese (room temperature)

  • 1 cup of powdered sugar

  • 1 tablespoon of vanilla

  • 1/4 cup of butter

  • Gummy worms or other favorite toppings


  • Crush cookies in a food processor or blender until cookies are finely crushed. Set aside.
  • In a mixing bowl, mix cream cheese, butter and powdered sugar until smooth. (I use a standing mixer but you can use a hand mixer).

  • In a separate bowl, whisk pudding mix, vanilla and milk for 2 minutes. Let it sit for a few minutes (2-3).
  • Slowly fold pudding into the cream cheese mixture.
    Then fold in coo[ whip.

  • Place about 1 Tablespoon of the crushed cookies into the bottom of each cup.
  • Then add a 2 Tablespoons of pudding to each cup.
    Then repeat another layer of cookies, then pudding, and then cookies.
  • Finish up by adding 2 gummy worms or any other fun topping to the top of each of the cups.
  • Refrigerate until well chilled, at least 3 hours and up to overnight.


  • Tips for crushing Oreos: Crush the entire cookie—do not remove the filling. You can crush your Oreos in a food processor or blender if you want them to be super fine. If you want chunky pieces of Oreos you can crush them in a Ziploc bag.
  • Pudding Flavors:  This recipe calls for French vanilla pudding or vanilla. My favorite is white chocolate pudding but it is sometimes hard to find. If you care a chocolate lover you can also use chocolate pudding.

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