Grease a ring mold with 1 tablespoon creamy salad dressing. Zest 1 orange and then peel both oranges.

Place oranges, orange zest, cranberries, and apples together in the bowl of a food processor; pulse until coarsely chopped. Strain fruit pieces, reserving juice in a quart-size measuring cup. Add enough boiling water to measure 3 cups liquid.

Dissolve unflavored gelatin in cold water in a large bowl. Pour water-juice mixture over unflavored gelatin. Add raspberry gelatin and 2 cups sugar; stir to dissolve completely. Stir in fruit mixture, grapes, and pecans. Pour gelatin mixture into prepared ring mold; chill 8 hours to overnight.

Mix whipped topping, cream cheese, 3 tablespoons creamy salad dressing, and 2 teaspoons sugar together in a bowl until dressing is smooth.

Dip chilled mold in a few inches of hot water to loosen gelatin from mold. Turn out onto a serving platter, garnish with parsley, and serve with dressing.