Line a 9-inch square baking pan with foil and lightly grease with cooking spray. Set aside.
In a medium saucepan, combine sugar, butter and evaporated milk. Set over medium-high heat and cook until boiling, stirring often, about 5 minutes.
Remove from heat, and stir in chocolate chips, marshmallow fluff, vanilla extract, and salt until melted through and completely smooth. Stir in the dried cherries, pour into prepared pan and spread out evenly. Allow to cool slightly and then cover with plastic wrap. Chill in the fridge until firm, about 1 hour. Dollop the top with the whipped topping and then swirl around with a spoon. Top with the halved cherries and sprinkle with the chocolate.
Chill once more for least 2 hours, or until completely firm. Slice and serve. Leftovers can be kept in the fridge, wrapped in plastic, for up to 4 days.