Preheat the oven to 350F. Line baking sheet with parchment paper.
In a large mixing bowl, whisk together the flour, baking soda, baking powder, salt, and cinnamon.
In another mixing bowl, whisk together the pumpkin puree, sugar, oil, eggs, and vanilla, until well combined. Pour into the dry ingredients and stir until well combined.
Using a small ice cream scoop, scoop the dough onto the prepared pan about 1 inch apart.Bake for 12 to 15 minutes or until a toothpick inserted into the center comes out clean. Remove from the oven and transfer to a wire cooling rack and let cool completely.
Filling
In a large mixing bowl, beat the butter, cream cheese, and vanilla together on medium-low speed until smooth.
With the mixer on low, gradually beat in the powdered sugar until fully combined. Transfer to a piping bag if desired.
Pipe or spread frosting on the flat side of half of the cookies. Press another cookie onto the frosting creating sandwiches. Chill for 30 minutes before serving. Store whoopie pies covered and refrigerated for up to 1 week. ENJOY!