Beat sugar and butter until well combined. Beat in eggs and egg white one at a time. Beat in vanilla.
Sift together flour, baking powder and salt. Add 1/2 of the flour mixture to the sugar mixture. Stir in milk. Add remaining flour mixture. Beat until smooth. Fold in chocolate chips.
Place cupcake liners in a cupcake pan. Fill each liner 2/3 of the way full.
Bake cupcakes for 15 - 20 minutes or until a toothpick inserted comes out with just a few crumbs on it.
Remove cupcakes from the oven, allow to cool a couple of minutes. Transfer to a cooling rack to cool completely.
While you are waiting for your cupcakes to cool, beat together powdered sugar and butter until fluffy. Stir in vanilla. Stir in milk until the frosting reaches a stiff but spreadable consistency.
Divide frosting into bowls. Use the yellow and red food coloring to make the orange for the pumpkin. Use the green to make the color for the stem. Use enough of each color to get your desired color.
Frost the cupcakes with the orange frosting. Use the green frosting to make a stem. Use the black decorating frosting to make desired faces on the cupcakes.