Mix dry ingredients: flour, baking soda, baking powder, cinnamon, nutmeg, and salt. Set aside for now.
In another bowl, cream sugar and butter together.
Mix in the egg, followed by the vanilla extract. Add in the pumpkin and mix.
Add in the dry ingredients and mix until a dough forms.
Preheat the oven to 350°F. Place dollops (of about 2 tbsp) of the sticky dough onto parchment lined baking sheets, there should be about 30 of them all together.
Wet your fingers and smooth out the dollops of dough to form flat ovals (they will puff up while baking). Place the sheets in the oven and bake for 10-15 minutes, or until firm.
Let cool on the sheets for 2 minutes, then move to a cooling rack.
Use a knife to cut out faces on your cooled pumpkin cookies. Poke out the cutout portions and brush off any crumbs. At the top of each cookie, cut a small triangular wedge for the stem.
Melt some semisweet chocolate. Spread ovals of chocolate about the size of the cookies on a piece of parchment paper.
Place a cookie on each chocolate oval. Use a spoon and place a dollop of chocolate at the top of each cookie where the wedge was cut out to form the stem.
If the stem isn't tall enough at first, wait for the first layer of chocolate to dry and then add another layer on top. Let all the chocolate dry. Then carefully peel the cookies off the parchment paper.
Finally, take a spatula, or another utensil with a thicker edge, like the blunt edge of a butter knife, and use it to press out/score vertical lines on the cookies to make them more pumpkin-like.