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

Double Stuffed Pumpkin Pie Oreos | halfbakedharvest.com

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.

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

Double Stuffed Pumpkin Pie Oreos | halfbakedharvest.com

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 | halfbakedharvest.com

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 | halfbakedharvest.com

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 | halfbakedharvest.com

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

Yeah, so Halloween.

Double Stuffed Pumpkin Pie Oreos | halfbakedharvest.com

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 | halfbakedharvest.com

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 | halfbakedharvest.com

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 | halfbakedharvest.com

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 | halfbakedharvest.com

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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Ingredients

Cookies

Pumpkin Pie Filling

Cream Filling

Instructions

  • 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.

Notes

*Oreos adapted from [Bakerella | http://www.bakerella.com/homemade-oreos/]
View Recipe Comments

Double Stuffed Pumpkin Pie Oreos | halfbakedharvest.com

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

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Comments

  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! ?

  3. Hello
    I just have a quick question before I try this recipe, the first paragraph you have written place the butter and chocolate chips in microwave, whisk in sugar, whisk in vanilla and again chocolate. I am not sure about the second time you mention chocolate in your first paragraph.
    We are having a competition at work for the best use and inventive of all the pumpkins we have grown and this one looks awesome so I want to make sure I do it right. I have printed out 4 of your pumpkin recipes (pumpkin & broccoli pizza, pull apart pumpkin cinnamon bread and molten chocolate one) and need to try them all out to see which one will get me the first prize 🙂 wish me luck

    Thank you

    Madlene

    1. HI! I am sorry, that is a typo and I took it out. No second chocolate now! 🙂

      Hope one of the recipes gets first prize, how fun!! THANKS!!

  4. I know that this is SUPER long but I’m so exhausted from baking 1 million things today & these cookies really pissed me off which is totally my fault. So I’m sharing with you what I did wrong or whatever.

    My problems with these cookies (they’re still kinda awesome though) & please don’t be offended just trying to give my honest opinion & “constructive criticism”:

    #1) The recipe is written really poorly. I mean this in the nicest way possible, maybe it could just use a look-over & a few tweaks to make it better understandable to the reader/baker. For example, step 1 says to add the chocolate & then the egg. I didn’t know what that was even talking about because the “chocolate” part was step 2 (& yes I read the whole recipe 1st but I cant remember everything 😉 ). It was also confusing to me that the freezing parts were in one single step. If it was me, I would’ve had them in separate steps to avoid any mix-up. Maybe I’m just really stupid, I don’t know, but I just felt like the recipe could be organized better.

    #2) That damn cookie dough (Lol I’m frustrated): I could not (for the life of me) get this dough to be the right consistency. It was soooo crumbly. I had to substitute 1/4 stick of butter with margarine (the best kind), but I really do not think that is what caused this. Before I began to roll it out (still in mixing bowl), there was just the biggest puddle of oil at the bottom. When I picked up dough, it literally could’ve been dripping in oil. I know this sounds like something I did wrong, but I swear you guys I did it exactly the way I was directed (minus the margarine part). I feel like something was not absorbing the butter well enough (& yes I added the flour etc. correctly). Once I rolled it out is when it began to get crumbly & crackly. Now, I will say that where I live, the weather right now is so dry, like zero humidity, so I’m thinking that took a big part. Once it was all ready to cut, it completely crumbled as I cut into it. Luckily, ended up using a cookie roller w/ wet hands to roll it out & a cookie cutter to make the circles. So tedious, not what I was expecting to have to do the night before Thanksgiving. Anyways, I probably made them too thick because they were like rock hard to roll which runs into my last complaint that I will get to of them being too rich (they baked beautifully though, also easy to overcook if you’re a ditz like me 😉 ).

    #3) The pumpkin filling: Perfect flavor, but it was waaayyy too runny to turn into filling. I added an extra pack of gelatin* & put it in the freezer for a half an hour (could probably do 1 extra hour max). After that, it was SO perfect! There was SO much leftover though. Literally I could make a half of a pumpkin pie.

    #4) The cream filling: It was so heavenly (& simple)! Literally sent from the Gods. Just a little leftover, but not really because I ate it.

    #5) The final result: In the end, my cookies were too rich. I know that cutting the cookies out too thick had a huge part in it, but at the same time I made 20 cookies (technically 40) which is more than the recipe provided for, so I’m surprised. My cookies were a little hard too (I probably overcooked… 15 min is how long they were in). I’ve never thought of myself to be sensitive to richer desserts. So, I am keeping them in an airtight container in the fridge overnight, hoping that tomorrow the super-soft whipped filling with be a matchable consistency to the cookies.

    I really do appreciate this recipe though, even though I’m burnt I had a blast making these!! Sorry if I offended in any way, that’s definitely not what my intentions were. I use a lot of your recipes (repeatedly), and this is the very first one I’ve ever had a problem with. Thank you!!!

    1. I’m so glad I found your comment. This recipe is so poorly written, I don’t even know where to start. It would have been good to have gone through this and edited it before posting.