Preheat oven to 350 degrees F. Line three baking sheets with parchment paper.
In a large bowl, whisk together the three cups of flour, two tablespoons cinnamon, one teaspoon of baking powder, one teaspoon of baking soda, one teaspoon of salt, one teaspoon of ginger and 1/4 teaspoon of nutmeg. Set aside.
In another separate bowl, using the electric mixer, whisk the granulated sugar and one cup of vegetable shortening. Then, add the pumpkin puree and whisk to combine thoroughly. Add the two eggs and one teaspoon vanilla and whisk until combined.
Add the flour mixture to the pumpkin mixture gradually and whisk until thoroughly combined.
Use a large spoon to add a heap of the pumpkin dough onto the parchment lined baking sheet a little more than one inch apart.
Bake for 20 minutes.
Check to see if the woopie pies are ready by inserting a toothpick into the center of the pie to see if it comes out clean.
Remove the woopie pies from the oven and let them cookies cool completely on a cooling rack.
For Cream Cheese Filling - In a mixing bowl, using an electric mixer on slow beat three cups of powdered sugar with the one stick of softened butter.
Increase to the mixing to medium to make the mixture crumbly.
Pour in two tablespoons of heavy whipping cream, one tablespoon of vanilla, eight ounces of cream cheese.
Beat on high speed for about three minutes until the Cream Cheese filling is smooth.
Place half of the Woopie pies upside down. Top with a generous sized amount of cream cheese filling. Make a Woopie Pie sandwiches with the other side. Try to pair similarly shaped Woopie Pies together.
The Pumpkin Woopie Pies can be stored in the fridge for about three days.