Tomato Contest In addition to the food, entertainment, and games, an annual highlight of the Pittston Tomato Festival is the Annual Tomato Contest. Everyone is welcome to enter his or her tomatoes at no charge in this contest. Ribbons will be awarded in four categories: Largest, smallest, ugliest, and most perfect. The contest will be held at the committee stand. Largest, Smallest, Ugliest, and Most Perfect Tomato Contest will be held on Saturday, August 23rdh at 6:30 pm, at the committee stand.