For the cookies
Have all ingredients at room temperature. Preheat oven to 375°F with a rack in the center.
Into a medium mixing bowl, sift together flour, baking powder, baking soda, cinnamon, ginger, nutmeg allspice, cloves, and salt.
In a large bowl or the bowl of a stand mixer fitted with the paddle, beat together the butter, granulated sugar, and brown sugar for two minutes.
Add the eggs one at a time, beating each until well incorporated.
Add the pumpkin and vanilla and beat until incorporated. (The mixture will look curdled at this stage. Don’t worry.)
Pour in the dry ingredients and mix on the lowest speed until just incorporated. You may want to do the last little bit of mixing by hand.
Line three large baking sheets with parchment paper (or lightly grease). Pipe or drop batter onto baking sheets about 1 heaping tablespoon at a time, to make 20 small cookies on each sheet (a total of 60).
Bake each batch for 8 minutes.
Cool completely on a rack before filling.
For the filling
Combine cream cheese, butter, vanilla and maple syrup in a medium mixing bowl or the bowl of a stand mixer fitted with the paddle.
Mix, starting on low and increasing speed to medium as you go, until smooth and well-combined, about 2 minutes.
Sift in powdered sugar and mix on the lowest speed until incorporated. Then increase speed and beat until light and fluffy, about 2 minutes more.
Spread or pipe icing onto the flat side of half the cookies and top with the remaining cookies to make sandwiches.
After assembling, place whoopie pies on one of the baking sheets and cover with foil (or transfer to airtight containers). Refrigerate for at least two hours to firm up the filling.