The night before, pour the cherry juice into ice cube molds and freeze.
To a blender, add the bourbon, Simple Syrup, bitters, cherry ice cubes and regular ice cubes and blend until smooth. Pour into rocks glasses or insulated tumblers and garnish with a thick orange peel.
Simple Syrup:
Combine the sugar and water in a small saucepot and bring to a simmer. Whisk until the sugar is dissolved, then chill until ready to use.
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