Preheat Oven: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
Mix Dry Ingredients: In a medium bowl, whisk together flour, baking powder, baking soda, salt, cinnamon, ginger, and cloves.
Cream Butter and Sugar: In a large bowl, beat together sugar and butter until light and fluffy.
Add Wet Ingredients: Beat in pumpkin puree, egg, and vanilla extract until well combined.
Combine Ingredients: Gradually mix in the dry ingredients until just combined.
Scoop Batter: Drop spoonfuls of batter onto the prepared baking sheet, spacing them about 2 inches apart.
Bake: Bake for 10-12 minutes, or until the whoopie pies are set and edges are lightly golden. Allow to cool on a wire rack.
Prepare Frosting: Beat together cream cheese, butter, powdered sugar, and vanilla extract until smooth. Adjust consistency with milk if needed.
Assemble Whoopie Pies: Spread frosting on the flat side of one cookie and top with another cookie to make a sandwich. Add chocolate chips and cream cheese as per choice as dressing.
Store: Keep whoopie pies in an airtight container in the refrigerator for up to a week or freeze for longer storage.