Pumpkin Pinwheel Cookie Sandwiches


Halloween is just around the corner (although if you have been to your local big box store in the last week you might be convinced that christmas is next week!?). The temperatures are steadily falling and it wont be long before the leaves are changing to golden brown, yellow, orange, and red. This also means that pumpkins are in season. Pumpkins pack a ton of flavor and are super sweet. They can serve more purposes than just being dissected by your kids to make a face that ultimately ends up looking more like roadkill in the end. While most of us associate pumpkin foods with pumpkin pie, there are many more applications for this wonderful creation that mother earth has given us. Today, we bring to you a fantastic use of pumpkins that will both please just about anyone (even those that claim to not like pumpkin) and make your taste buds dance around like a gymnast on a trampoline. These cookies are sweeter than your favorite grandmother and pack more pumpkin flavor than you could get if you just chomped on a raw pumpkin.

I first came upon the idea of a pumpkin pinwheel cookie about 5 years ago now where I first prepared them for a seminar that I gave at Penn State. They were a huge hit and people were begging for more. Well, they never got them since I left Penn State shortly thereafter to head to California. I have made them several time since, but this is the first time that we took the pumpkin pinwheel cookies and made cookie sandwiches out of them. We were not disappointed. The cookies are stellar by themselves, but when you sandwich some cream filling between two of them, oh my, your taste buds just get all jittery. These pumpkin pinwheel cookies are perfect once filled or you can freeze them and eat them like ice cream sandwiches when you care craving something sweet at midnight.

The cookies are pretty straightforward but do require some time. The key step to making the pumpkin pinwheel cookies is freezing the dough log before cutting the cookies. An hour is required to do this but I would highly recommend letting the dough sit for several hours if not over night. You will thank me later. If you rush this step, the dough and filling will be too soft and the cookies will just turn into blobs when you try to cut them. Having a solid dough also prevents the cookies from spreading out into something that looks like it was run over by a semi. The cookies are topped with a sweet brown sugar and pumpkin pie spice crumble that gives the cookies a nice contrast in texture.

One last thing . . . you might want to double or triple this recipe since they will be gone before you know it. And, you can make these cookies at any time of the year since we use canned pumpkin puree.

Enjoy and we hope that your sweet tooth finds our pumpkin pinwheel cookie sandwiches fulfilling.

Creamed sugar and butter.

Dough after the egg and vanilla are added.

Dough rolled to 13 inches by 9 inches.

Pumpkin, brown sugar, and spice mixture.

Pumpkin pinwheel cookie dough with the pumpkin spread on the dough. Now it is time to roll!

Dough roll ready to be frozen (don’t skip the freezing step or else your pinwheels will become pin-blobs).

The pumpkin pin wheel cookies have been topped with the brown sugar crumble and are ready for the oven.

Pumpkin pinwheel cookie sandwiches.


Pumpkin Pinwheel Cookie Sandwiches
Prep Time
15 min
Cook Time
12 min
Total Time
27 min
1 dozen


  • 1/2 cups white sugar
  • 3/4 cups light brown sugar
  • 1 cup butter (room temperature)
  • 1 egg
  • 1 teaspoon vanilla extract
  • 2 1/4 cup all-purpose flour
  • 1/4 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1 teaspoon ground cinnamon
  • 1/2 teaspoon ground nutmeg
  • 1/2 teaspoon ground allspice
  • 1 cup canned pumpkin
  • 2 teaspoons + 1 teaspoon pumpkin pie spice (equal parts ground cinnamon, nutmeg, and allspice)
  • 1/2 cup + 1/2 cup light brown sugar
  • 1 tablespoon butter (melted)
  • 4 ounces cream cheese
  • 1/2 cup butter
  • 2 cups powdered sugar
  • 2 tablespoons whole milk


  • In a stand mixer, cream the butter and sugars together until smooth. Add the vanilla extract and egg to the butter and sugar mixture and combine fully. Sift the flour, cinnamon, nutmeg, allspice, salt, and baking powder together and slowly add to the stand mixer on low speed. Once all of the dry ingredients have been added, switch to medium speed until the dough comes together. It should be quite stiff.
  • Place the dough between two sheets of wax paper and roll into a rectangle about 13 inches by 9 inches. The dough should be about a half inch thick. Place the dough in the freezer for 10-15 minutes to harden a bit.
  • Meanwhile, in a small mixing bowl, combine the canned pumpkin, pumpkin pie spice, and 1/2 cup of brown sugar. Mix with a spoon until the sugar and spices are evenly distributed.
  • Once the dough has hardened slightly, remove it from the freezer and carefully pull off the top layer of wax paper. Spread the pumpkin mixture on the dough. Be sure to cover the dough completely and be careful not to spread it to thick (you want a thin layer or else it will squirt out the sides when we roll it).
  • To roll, carefully fold over one end (the long side) and begin to roll. If the dough breaks, just rub the cracks with your finger to smooth it out. Continue rolling until your reach the other side of the dough. Wrap the log in the sheet of wax paper and place in the freezer for at least an hour (you could leave it overnight if you want to).
  • After the dough has rested for at least an hour, preheat your oven to 350 degrees F.
  • Remove the dough from the freezer and place it on a cutting board. With a very sharp knife, cut the dough into 1/2-3/4 inch thick slices and place on a cookie sheet.
  • In a small mixing bowl, combine the remaining 1/2 cup of brown sugar and the remaining 1 teaspoon of pumpkin pie spice with the melted butter. Sprinkle the brown sugar crumble over the cookies.
  • Bake the cookies for 10-12 minutes or until the brown sugar crumble begins to get crisp. Remove from the oven and transfer to a wire rack to cool.
  • To prepare the cream filling, cream the butter and cream cheese in your food processor until smooth and completely combined.
  • Gradually add the powdered sugar to the creamed butter and cream cheese. Add 2 tablespoons of milk to the cream filling in the stand mixer to bring the cream to the correct consistency.
  • To prepare the cookie sandwiches, use a spatula to spread about 1 tablespoon of the cream filling on the bottom of one pumpkin pinwheel cookie. Place another pumpkin pinwheel cookie on top and serve.


Web Analytics