Preheat the oven to 350 degrees. Line a couple baking sheets with parchment and set aside.
In the bowl of a stand mixer, combine the sugar, brown sugar and oil. Mix until combined.
Add in the pumpkin puree, eggs and vanilla. Mix until combined.
Add in the flour, salt, baking soda, baking powder and pumpkin pie spice. Mix just until combined, scraping the sides often, but don’t over mix.
Using an ice cream scoop, place dollops of the dough on the prepared baking sheets.
Bake in the preheated oven for 10-12 minutes or until the centers are set. Allow to cool completely before removing from the pan and the parchment to assemble.
For the frosting - in the bowl of a stand mixer fitted with the paddle attachment, mix the butter until smooth.
Add in the softened cream cheese and mix until smooth.
Add in the powdered sugar and vanilla and mix until combined. Bump up the speed to medium and mix until smooth and fluffy, scraping the sides often.
Transfer the frosting to a piping bag, set aside.
Once the cookies are cool, partner them up with similar size and shaped cookies.
Cut a hole in the end of the piping bag and pipe a mound of frosting on one half of the cookies.
Sandwich with the other half to complete the whoopie pie.
Notes
Storage: Whoopie pies should be stored in an airtight container in the fridge for up to 3 days.