Preheat oven to 425°F. Prepare cookie dough as directed. Reserve 1 cup cookie dough; set aside.
Press prepared cookie dough into greased 9” pie pan, covering the bottom but only going up the sides about halfway.
For Pie Filling:
In mixing bowl, combine all dry ingredients. Beat in 2 eggs, evaporated milk and pure pumpkin. Pour over cookie shell. Carefully cover edge of pie with tin foil to prevent over-browning.
Bake at 425°F for 15 minutes. Reduce heat to 350°F; bake 40-50 minutes or until knife inserted near center comes out nearly clean. Center will be set, but may still jiggle. Remove from oven; let cool.
Using reserved 1 cup cookie dough, press and flatten on cookie sheet to about 1/4” thickness. You’ll be cutting jack-o-lantern eyes, nose and mouth from these sections, so size them appropriately. Bake 350°F for 10 minutes. Let sit briefly, but while still warm, trim the cookie into desired jack-o-lantern shapes.
For whipped cream topping:
Beat together whipping cream and orange food coloring until soft peaks form. Add 1 teaspoon vanilla and 1 1/2 tablespoon sugar.
Beat until whipped cream forms stiff peaks. Pipe on completely cool pie as desired.