Preheat the oven to 350 degrees.

In the mixing bowl of a stand mixer, add the Butter, Sugar, Eggs, and Vanilla, and blend on Medium speed until light and fluffy.

Add Flour one cup at a time, and mix on low speed until all the Flour has been added, and a soft cookie dough has formed. 

Place about 1/4 of the dough on a floured surface, and with a rolling pin, roll the dough to 1/4 inch thick.

Cut out the cookies with the Cookie Cutters, and place on baking sheets, and bake for 8 to 10 minutes. Continue until all the cookie dough has been rolled, cut out, and baked. 

When cookies are baked,  remove from the oven and place cookies on a wire rack to cool. 

While the Cookies are cooling, make the Frosting.

In the mixing bowl of a stand mixer, mix the Powdered sugar, Milk, and Vanilla on low speed until blended, then mix on higher speed until mixed completely. 

Divide the Frosting evenly, into three individual dishes or Ramekins. 

Add a few drops of food coloring to the Frosting, and stir well until desired color is reached.  Add colored Frosting to clear piping bags, and snip off the tip of each bag, leaving a small opening at the tip of the bag.

Pipe the Black Frosting in the opening for the eyes and mouth. Sprinkle the Black Sugars on top of the Frosting, and with a small brush, brush away any excess sugars. 

Pipe the Orange Frosting around the edges of the cookies, then fill in each cookie with the Orange, all but the cut outs for the eyes and mouth. 

Pipe the Green Frosting onto the stem of the cookies, and Sprinkle with Halloween Sprinkles on the stem.

Pipe thin lines of Orange Frosting down the Cookie to mimic pumpkin spines.

Serve and Enjoy!