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Molasses cookie cups are filled with delicious pumpkin pudding then topped with fresh whipped cream, everyone will love this delectable fall recipe!
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Have you seen my last two fall recipes? No? That’s okay! I will be using both Spiced Molasses Snap Cookies and Homemade Pumpkin Pudding in this easy thanksgiving dessert recipe!
Let’s think about Thanksgiving for a second. All the delicious fixings, stuffing, sweet potatoes, corn, the turkey, and every year we eat too much! Nothing is worse than when your tastebuds crave dessert but your stomach just won’t allow it! I am totally guilty of baking way too much but pumpkin pie cookie cups are the perfect ending to your fall gathering! Not only are the little bite-sized pieces of heaven delicious but they are EASY! I prefer to make everything from scratch but if you like a little semi-homemade action you are more than welcome to buy the Jello brand pumpkin pudding. If you don’t want all those preservatives I suggest you use my microwavable recipe, Homemade Pumpkin Pudding.
If you caught my Spiced Molasses Snap Cookies you may remember I purposely wanted them nice and crunchy. Firstly because it’s nice to have a crunchy cookie every now and then but secondly I wanted a sturdy base for this dessert. If you have been following me for a while you may recall my Oreo Cookie Pudding Bars, the cookie bars inspired these pumpkin pie pudding cups!
Why are they called pumpkin pie cookie cups?
Alright so they aren’t really pumpkin pie but once you pair the pumpkin pudding with the spiced molasses cookies you will be in heaven. They are a bit different than the traditional pumpkin pie flavor but still delicious, your pumpkin haters may actually enjoy this one!
Is this your recipe?
Sort of, the molasses cookie recipe was adapted from Taste of Home because I wanted a crunchy cookie for this base. The pumpkin pudding is completely my recipe and the idea was mine as well.
How do I make Pumpkin Pie Cookie Cups?
Well first off whatever you do make sure your pumpkin pudding is made on the same day you plan to serve the Pumpkin Pie Cookie cups so the pudding is super fresh. Your choice here you can buy a boxed pumpkin pudding or make my Homemade Pumpkin Pudding. The cookie cups can be made a day or two in advance but do not fill them until the day you plan on serving (as the pudding sits in the cookie cup it will soften the cup, the longer they sit the softer they get).
Time to make the molasses cookie cups, mix up your dough, and grab a couple of mini cupcake pans. Be sure to lightly spray the pans with Pam baking spray. Get a medium cookie scoop and add a ball to 48 mini cupcake indents, I slightly pressed the balls down into the indent but made a well after they were baked. Bake your cookie cups and once baked create a well with the handle of a wooden spoon. Allow them to cool in the pan for 5 mins before letting them cool completely on the counter or wire rack. Once your cookie cups are cooled and your pudding is set you may want to make whipped cream if you would like a little dollop on top like I did or you can purchase premade.
Now for the assembly, you will want to grab 2 small/medium Ziplocs or 2 pipping bags. Line 2 short cups with the opened Ziplocs and fill one with pudding and one with whipped cream. Next, close the bags making sure to release the air inside. Take the pumpkin pudding bag and cut a small slit on one of the bottom corners, then pipe into cookie cups. Once you are done evenly filling the molasses cookie cups with pudding, cut a smaller slit on one bottom corner of the whipped cream bag. Add a little squirt/dollop to the tops of each cookie cup and if you like having a little crumble on top crumble 1-2 cookies and sprinkle on top of each cup. There you have it, pumpkin pie cookie cups!
Can I make half the amount of cookie cups?
Yes, you can, you could easily just make 24 cookie cups and use half the amount of pudding and half the amount of whipped cream but keep in mind an entire spiced molasses snap cookie dough yields up to 60 cookies or cookie cups. I like to make 48 cookie cups and 12 cookies but you can easily make 24 cups and 36 cookies instead. I like to have extra cookies around for the tops of the cups.
Will I have extra ingredients left over?
Yes, you probably will. You can get away with making half of the pumpkin pudding if you are worried the pudding won’t get eaten but keep in mind halving the recipe means half the amount of microwave time for my pumpkin pudding recipe. I use 1 cup of heavy cream to make the whipped cream and there will be a bit leftover on that. Since I don’t mind extra pudding I sometimes will dip the cookies in the pudding and top with the remaining whipped cream!
Can this be made vegan, dairy-free or gluten-Free?
For both of the recipes, I noted how to adapt them to these dietary concerns. Since I was able to figure out adaptations for these dietary needs yes, you can make them vegan, dairy-free, or gluten-free. I would like to let you know I have not tried making these cookie cups vegan/DF/GF so try this at your own risk. To make the whipped cream I would recommend Silks Heavy Cream Alternative, I have tried this and it works great!
Pumpkin Pie Cookie Cups
- Stand Mixer
- Mini cupcake pan
- Cookie sheet
- Medium Cookie Scoop
- Hand mixer
Spiced Molasses Cookie Cups
- 3/4 cup unsalted butter softened or vegan butter sub
- 1/2 cup brown sugar
- 1/2 cup granulated sugar
- 1/3 cup molasses
- 1/4 cup 2/% milk or vegan milk sub
- 1 tsp vanilla extract
- 2 1/4 cups all-purpose flour or bobs red mill gluten-free baking flour
- 2 tsp baking soda
- 1 1/2 tsp ground cinnamon
- 1 tsp ground ginger
- 1/2 tsp ground cloves
- 1/4 tsp ground all spice
- 1/2 tsp salt
- 3/4 cup prepared pumpkin pudding homemade or jello brand
- 1 cup heavy whipping cream or silk heavy cream alternative for vegan sub
- 1/8 cup confectionary sugar
- 1/2 tsp vanilla extract
- For the cookie cups, in a small to medium bowl whisk flour, baking soda, salt, and spices, set aside.
- Preheat oven to 350°. Spray two mini cupcake pans with pam baking spray (48 total indentations) then line 1 cookie sheet with parchment paper and set aside.
- In the bowl of a stand mixer, cream butter, brown sugar, and granulated sugar until light and fluffy. Then beat in the molasses, milk, and vanilla extract.
- Gradually beat flour mixture into creamed mixture.
- Using a medium cookie scoop create rounded dough balls, add one ball to each of the 48 mini cupcake indents and slightly press the balls down into the indent, don’t make a well just a lightly push down. With the remaining dough, you should get 12 more dough balls, place them 2-in. apart on parchment-lined baking sheets. Slightly smoosh down with your hand.
- Bake twelve cookies, take 10-15 minutes, or until edges begin to set. The cookie cups take 20-25 mins to bake. Cool the twelve cookies on pans for 5 minutes. Remove to wire racks to cool completely. When cookie cups are set take them out and while still hot create an indent with the handle of a wooden spoon. Cool the cookie cups in the pan for 5 mins-10 mins, until you can take them out of the cups, allow to cool completely on the counter or wire racks.
- If you haven’t already made your Pumpkin pudding do so, you can use my homemade pumpkin pudding recipe or Jello brand, make sure your pudding is set prior to assembly.
- If making whipped cream, with your hand mixer or whisk whip heavy cream, sugar, and vanilla extract until whip cream texture.
- For a neat assembly, you will want to grab 2 small/medium Ziplocs or 2 pipping bags. Line 2 short cups with the opened Ziplocs and fill one with pudding and one with whipped cream. Close the bags making sure to release the air inside.
- Take the pumpkin pudding bag and cut a piece small off of one of the bottom corners, then pipe into cookie cups.
- Once you are done evenly filling the molasses cookie cups with pudding, cut a smaller piece off of one of the bottom corners of the whipped cream bag. Add a little squirt/dollop to the tops of each cookie cup and if you like having a little crumble on top crumble 1-2 cookies and sprinkle on top of each cup.
I hope you give this bite-sized easy thanksgiving dessert a try! Let me know in the comments what your favorite foods are for thanksgiving!
Hey there! I’m the owner & author of Life Is Homemade (the blog), as well as Mad About Madeleines. I hope you enjoyed some of the delicious recipes, how-to’s, DIYs, & product reviews I blogged about. Thank you for your previous support I hope you stick around on my new journey with Mad About Madeleines.