Preheat oven to 350℉ and line cookie sheets with parchment paper or silicone baking mat.
To Make Cookies
In a medium mixing bowl whisk together flour, baking powder, baking soda, cinnamon, pumpkin pie spice and salt; set aside.
In the bowl of electric mixer beat butter and sugar on medium speed until well blended, about 2 minutes. Add eggs, one at a time, beating well to incorporate between each addition. Add pumpkin and vanilla extract, beat until well blended.
Add flour mixture and beat on low just until combined. Do not over mix.
Using a 1 tablespoon scoop, or heaping teaspoons, drop batter onto prepared baking sheets, leaving room for expansion between each cookie. Bake in 350℉ oven for 10-12 minutes, just until bottom is set and cookie springs back when gently pressed. Allow to cool a few minutes on baking sheet then transfer to cooling rack to cool completely.
You will need 72 cookies to make the final 36 whoopie pies.
To Make Cream Cheese Filling
Beat cream cheese, 6 tablespoons butter, ½ teaspoon vanilla extract, 1 tablespoon sugar and ¼ teaspoon cinnamon until light and fluffy. Add 1 ½ cups powdered sugar a half cup at a time, beating on low between each addition, then increase speed to medium high and beat until light and fluffy.
Notes
Store assembled cookies in a single layer in an airtight container in the refrigerator for up to 3 days, or for longer storage freeze for up to a month.