Cream together butter, sugar and vanilla in a large mixing bowl for 3-5 minutes, until light and fluffy. Add the eggs, one at a time, and mix until evenly combined. Add the flour, baking soda, cinnamon, ginger, nutmeg, and salt, beat until combined and the dough forms a ball.
Generously flour your work surface to prevent your dough from sticking. Divide the dough in half and roll out the dough to 1/4 inch thickness. Cut out the cookies using a pumpkin cookie cutter. Carefully transfer the cookies to a parchment lined baking sheet and cut eyes and a mouth in half the cookies using a pairing knife or cookie cutter. Roll out the leftover scraps, and repeat with the remaining disk of dough.
Cover the baking sheet and place the sheet in the freezer for about 15-20 minutes, until firm.
Preheat oven to 350 degrees. Bake the cookies on the middle rack of the oven for 8-12 minutes, or until just lightly golden brown. Be careful not to over bake, and allow cookies to cool completely.
Add the butter to a medium pot. Allow the butter to slightly brown until it smells toasted, about 2-3 minutes. Stir often. Remove from the heat and let cool 5 minutes. Brush the butter over the top half of the cookies and then sprinkle the cookies with cinnamon sugar.
Spread the melted milk chocolate over the half of the cookies with no face. Place the top pumpkin faced cookies over the chocolate, gently pressing to adhere.