For my third pie cookie concept, I went with the obvious choice for this time of year: Pumpkin Pie! Pumpkin pie cookies were a tough one to figure out. After making the Lattice Pie Cookies a few times, I had a pretty good idea of how to shape the open-shell pie shapes but creating the right filling proved to be more tricky. After testing basic recipes, it became clear I had to come up with a no-bake version. I also had to figure out a way to keep the cookie base dry, even with a wet filling on top. All it took was a motivated afternoon and a willing taster (Thanks Sam!).

So here they are, just in time for Halloween celebrations and Thanksgiving dessert tables: Pumpkin Pie Cookies!

Pumpkin Pie Cookies
 

makes 10 cookies
Ingredients
  • for the cookies:
  • 2 sticks of butter, room temperature
  • 1 cup sugar
  • 1 egg
  • 1 tsp vanilla extract
  • 2½ cups flour
  • ½ cup white chocolate
  • for the filling:
  • 1 15oz can of pumpkin puree
  • spices as directed on pumpkin puree can for pumpkin pie filling
  • 1 box of instant vanilla pudding
  • 2 cups milk

Instructions
  1. In the bowl of an electric mixer fitted with the flat beater, cream butter and sugar on medium speed until light in color and fluffy in texture. Add the egg and vanilla extract. Mix until combined. Add all the flour and mix on low speed until the dough comes together.
  2. Roll out your dough between 2 pieces of plastic wrap and refrigerate for at least 30 minutes. In the meantime, preheat your oven to 350°F.
  3. Unwrap your dough and cut out your cookies. Bake for 12 minutes or until the edges start to turn a light golden color.
  4. Melt white chocolate and brush onto cookies as a seal before adding the pumpkin filling.
  5. To make the pumpkin filling, mix pumpkin puree with spices listed for pumpkin pie on the side of the can. In a separate bowl, prepare instant vanilla pudding according to directions (add 2 cups of milk). Mix pumpkin mix and pudding together. Pour a few tbsp of pumpkin filling on each cookie. Place in the refrigerator to set.

In the bowl of an electric mixer fitted with the flat beater, cream butter and sugar on medium speed until light in color and fluffy in texture. Add the egg and vanilla extract. Mix until combined. Add all the flour and mix on low speed until the dough comes together.
Roll out your dough between 2 pieces of plastic wrap and refrigerate for at least 30 minutes. In the meantime, preheat your oven to 350°F.

To shape the cookies, I am using 2 fluted circle cutters. If you don’t have any of those, here is a link to an affordable set that will last you a lifetime:

Ateco Fluted Round Cutter Set

I am using 2 of the larger ones. Unwrap your dough and cut fluted circles:

Set half of your circles onto a lined baking sheet. Those will be our bases. To build the pie edge, take one of the other fluted pieces of dough and cut out its center using a slightly smaller cutter than your original:

Set the edge circles on top of the bases, re-roll all the extra dough and repeat:

Bake your pie shell cookies for 12 minutes or until the edges start to turn golden.

Now before we prepare the pumpkin filling, here is a trick that will prevent your cookies from getting all soggy. We are going to use white chocolate as a sealer. To do that, melt some white chocolate in the microwave. I used a piping bag but looking back, that was completely unnecessary. A Pyrex cup will work just fine:

Put a dab of white chocolate in the center of your cookie and spread it all over the base and up the sides where the filling will go:

It really doesn’t take much. As the chocolate sets, it will prevent the wet filling from ruining your cookies.

To make the filling, empty a 15oz. can of pumpkin puree into a bowl and add the spices listed on the can for a traditional pumpkin pie (cinnamon, ginger, cloves, salt, sugar). I only put half the sugar listed on the can:

Mix until combined. In a separate bowl, prepare instant vanilla pudding according to directions (add 2 cups of cold milk). Whisk together. Before the pudding sets, add the pumpkin mixture:

Stir until combined. Immediately pour a few tbsp of pumpkin filling on each cookie:

Shake each cookie to spread the filling:

The cookies will only need so much filling so feel free to pour the rest into ramekins for later. Trust me, Pumpkin Pie Pudding sound delicious to just about everyone. Place your cookies in the refrigerator to set.