Make the cookie dough: cream together butter and sugars. Beat in the yolk, and red and yellow food colorings.
2. Stir remaining ingredients together, and add to butter mixture. Mix well. Chill for 4 hours or overnight.
3. Roll dough to 1/8" - 1/4” thickness, and cut into pumpkin shapes with a cookie cutter. Using a small, sharp knife, cut triangle eyes and noses on half of the pumpkins. You can also draw curved lines with the tip of a knife on the surface of the cookies, to mimic the ridges on a real pumpkin - just be careful not to cut all the way through the cookie.
4. Bake at 350° F for 8 - 10 minutes, or until the edges are just barely, or just about to, brown. Cool completely on a wire rack.
5. To make the frosting, cream together butter and 1 cup of the powdered sugar. Stir in vanilla, salt, and milk. Stir in remaining powdered sugar. When sugar is completely incorporated, add food coloring and stir until frosting is uniform. Optional: Whip in a stand mixer on high speed, to yield more fluffy, voluminous frosting.
5. When completely cool, spread the non-face pumpkins with the icing, and top with the pumpkins with faces. DO NOT try to press the top cookies down to make the icing squeeze up through the cut-outs - it will just break the cookies.