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Would you believe me if I told you I did not like Oreos?

Double Stuffed Pumpkin Pie Oreos |

Probably not, considering I have made peanut butter dipped Oreos, chocolate dipped homemade peanut butter Oreo mocha ice cream sandwiches and more recently these peanut butter cup cookies and cream salted caramel popcorn bars.

And I mean, that was all within the last ten months.

PicMonkey Collage

You also probably wouldn’t believe me because, I mean who the heck does not like Oreos?

Double Stuffed Pumpkin Pie Oreos |

Well me, but only sorta.

When I say I don’t like Oreos, I really only mean the store-bought ones. But that’s only since I started making homemade Oreos. Store-bought Oreos? Sure they are good and actually they are really good in treats like these gooey chocolate Oreo crunch butter cake bars because they hold up a million times better when being stuffed INTO something and baked again, but when eating them alone?

Sub par, they have nothing and I mean nothing on a homemade Oreo.

Double Stuffed Pumpkin Pie Oreos |

Basically what I am saying is, I am a homemade baked goods brat.

Just a straight up, spoiled rotten brat. Seriously, don’t try to feed me store-bought Oreos. Either hand me a bucket of peanut butter to dip those suckers in (YES!! Do this) or stuff them in something homemade and awesome.

Double Stuffed Pumpkin Pie Oreos |

I was planning on waiting until closer to Thanksgiving to post these, but then I made them and just plain freaked out at their awesomeness.

Ok fine, and their cuteness.

Double Stuffed Pumpkin Pie Oreos |

Plus, they are kind of fun for Halloween. Orange and black?

Yeah, so Halloween.

Double Stuffed Pumpkin Pie Oreos |

And since we are on the Halloween subject, you should know that it has been snowing here.

Half the day yesterday and it is predicted to continue on all day today. I kind of love it. To me it screams cozy, snuggle in and bake cookies weather. The kind of weather that reminds me of  when my mom and I (and probably a handful of brothers + friends) would bake chocolate chip cookies on a cold rainy October Cleveland day (swap the rain for snow here though, it never rains in October).

Those were the best days, especially when those days fell on a Friday. Friday meant no school for two whole days.

That was a big fat AWESOME in my brain.

Double Stuffed Pumpkin Pie Oreos |

Making these is no harder than making any other cookies, they just require some time to chill in the fridge.

If you can make cookies and do some stirring, you can make these.

Double Stuffed Pumpkin Pie Oreos |

The pumpkin pie filling is actually true pumpkin pie filling.

Oh yes, oh yes, it is incredible. Seriously, I could eat that stuff with a spoon. SO good.

I made my own pumpkin purée by roasting a sugar pumpkin and puréeing it in my food processor. If you have time, do this!! It is a trillion times better and seriously so easy. Plus, so worth it.

Double Stuffed Pumpkin Pie Oreos |

The rest is pretty simple.

Oreo meets pumpkin pie and they make one heck of a cookie. I just really don’t even know what else to say. Just do it. Do it now. Make them over and over and over again until December twenty-fifth when you have decided you just can’t take anymore pumpkin. Does that happen?

Oh and the best part about making your own Oreos?

Double Stuffed Pumpkin Pie Oreos |

Pumpkin Cream Pie Oreos

Prep Time 30 minutes
Cook Time 30 minutes
Rest 2 hours
Total Time 3 hours
Servings: 18 Cookies
Calories Per Serving: 286 kcal

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

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Pumpkin Pie Filling

Cream Filling


  • In a medium microwave safe bowl, place the butter and chocolate chips in microwave, stirring every 30 seconds until melted. Whisk in the sugar until well combined. Whisk in the vanilla and chocolate. Whisk in the egg until combined.
  • In another bowl, whisk flour, cocoa, salt and soda until combined. Stir flour mixture into the chocolate mixture. Beat with a mixer until the dough comes together as a solid.
  • Transfer the dough to a sheet of wax paper. Shape into a log about 2 1/2 inches in diameter. Place log along the edge of wax paper and roll. Shape as you roll to maintain a smooth cylinder. Twist ends of paper to secure and help keep the shape compact. Refrigerate at least two hours or until firm. If log settles and flattens on one side, rotate every 15 minutes or so to maintain a round shape. Or you can transfer the dough to a sheet of wax paper. Shape into a log about inches 7 to 8 in diameter. Place log along the edge of wax paper and roll. Shape as you roll to maintain a smooth cylinder. Twist ends of paper to secure and help keep the shape compact. Refrigerate at least two hours or freeze one hour until firm.
  • While the dough chills make the pumpkin pie filling. In a heavy saucepan combine gelatin, cinnamon, ginger, nutmeg, and salt. Stir in condensed milk and beaten eggs, mixing well. Let stand one minute, then place on burner over low heat, stirring constantly for about 10 minutes, or until gelatin dissolves and mixture thickens. Stir the the pumpkin and vanilla until completely smooth. Remove from heat and place in the fridge for one hour.
  • Heat oven to 325 degrees and line baking sheet with parchment paper.
  • Cut dough in quarter inch thick slices and place on prepared baking sheet. Bake for about 12-18 minutes or until cookies are firm to the touch. Just watch them because it’s hard to tell by looks if they are done especially since they are so dark to begin with. If your cookies are small circles, they will only need 12-15 minutes and if they are bigger circles they will need closer to 18-20 minutes.
  • Cool and prepare the cream filling. In a mixer, beat the butter until smooth and creamy. Add sugar and vanilla and beat until smooth.
  • Grab the pumpkin pie filling and place it in the bowl of a stand mixer or a large bowl. Beat the filling until smooth and whipped, about 2 minutes.
  • To assemble the cookies, spread a little of the pumpkin pie filling on half of all the cookies, be generous with the filling. Now spread the cream filling on the remaining half of the cookies. Sandwich the pumpkin pie cookies with the cream cookies. Now eat them!!
  • Store in an airtight container in the fridge or on the counter.


*Oreos adapted from [Bakerella |]

Double Stuffed Pumpkin Pie Oreos |

You can not only double stuff, go ahead and live dangerously – triple stuff!

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  1. 2 questions:
    1) Shouldthe butter be melted, cooled, and then demented with chocolate chips?
    2) How much gelatin do you need. 1 oz or 0.25?

    1. Hi Heather! Yes, the butter does not need to be melted, it will melt with the chocolate chips. You need .25 ounces of gelatin. Recipe has been fixed! Please let me know if you have any other questions. I hope you love this recipe! Thank you!! xTieghan

  2. These would be perfect for a fall themed baby shower I am hosting. Could the chocolate cookies be made ahead of time and frozen?

    1. Hi Patti, yes the cookies can be made ahead and frozen, then thawed. It will work great! 🙂 Let me know if you have other questions. Enjoy!

      1. Thanks! Made the cookie part last weekend and they did freeze beautifully. Now a question about the pumpkin layer. I have a 1 oz box of gelatin with 4 packets of .25 oz each in it. Do I use all 4 packets?

        1. Hi! Just use 1 packet of gelatin. Please let me know if you have any other questions. Hope you love this recipe! Thank you! ?

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