Ready In: 1 hr 5 mins
Prep: 30 mins
Cook: 35 mins
Yields: 40-45 Servings
Cream Cheese Filling
Make the whoopie cookies: Preheat oven to 350 degrees. Line baking sheets with parchment paper and set aside.
In a large bowl, whisk together flour, salt, baking powder, baking soda, cinnamon, ginger, and cloves; set aside. In another large bowl, mix together brown sugar, sugar, oil, Greek yogurt and half & half until well combined. Add pumpkin puree and mix until combined (it should be pretty soupy). Add eggs and vanilla and mix until well combined. Add flour mixture to pumpkin mixture and mix until fully incorporated.
Using a melon baller with a release mechanism, drop dough onto prepared baking sheets, about 1 inch apart. Bake for 8-10 minutes until they look dry and fluffy (great time to taste test them to ensure they are cooked all the way through). Transfer cookies to a cooling rack to cool completely.
Make the filling: Sift confectioner' sugar into a medium bowl; set aside. In another bowl, using an electric mixer, beat softened butter until smooth. Add cream cheese and beat until well combined. Add confectioners' sugar and vanilla, beat just until smooth. (Filling can be made up to a day in advance. Cover and refrigerate; let stand at room temperature to soften before using.)
Assemble the whoopie pies: When cookies have cooled completely, use a butter knife to smear the filling onto the flat side of one of the cookies. Sandwich with another cookie half, pressing down slightly so that the filling spreads to the edge of the cookies. Use as much or as little cream as you desire (I had quite a bit left over so smear away)!
NOTES: If you want to make 12 traditional large-sized whoopies, use a small ice cream scoop and bake the cookies for about 15 minutes.