Make devils' food cupcakes according to package directions on box. Let cool completely. While cupcakes are cooling, prepare frosting.
Mix sugar and butter on low speed. Increase speed to medium and beat for approximately 3minutes.
Add vanilla and milk and beat on medium for another minute or so. Add more milk if necessary. Frost cupcakes once cooled.
Take one Circus Peanut and cut it in half. Take one of the halves and roll in your palm until round and smooth. Using a toothpick, make vertical lines on the Circus Peanut pumpkin, mimicking the ridges on a pumpkin.
Then cut a sliver from a green gumdrop and place on top of your pumpkin to create the stem. Place a pumpkin (or two) on top of each cupcake. The frosting will keep the pumpkin in place.