For each serving: Blend 1/4 cup milk, 2 Tbsp. cherry dessert topping, 1 Tbsp. chocolate syrup, 1-2/3 cups ice cream, 5 Tbsp. OREO Pieces and 3 Tbsp. Variegate in blender until well blended.
Pour into tall chilled glass; top with 1 Tbsp. whipped topping, additional 1 tsp. OREO Pieces and maraschino cherry.