Pour 2 cups cold water in a 6-cup bundt pan. Scatter 1 cup of the cherries in the water. Freeze for 2 hours, making sure the pan is level. Add 2 more cups cold water and 1 cup cherries to the pan and freeze until solid, about 2 hours more.
When you are ready to serve, place the bundt pan on a baking sheet open-side up. Run cool water over the top of the pan until you hear the ice cube release onto the baking sheet. Gently transfer to a 3-gallon punch bowl.
Add the bourbon, sweet vermouth and Aperol to the punch bowl. Stir to combine. Add ice to rocks glasses, ladle in the cocktail and garnish each with a maraschino cherry.
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