• Begin by freezing fresh orange wedges until solid.
• In a blender, combine ½ a frozen orange (around 5 wedges), 2-3 frozen cherries, ½ ounce brown sugar simple syrup, 2 ounces bourbon, and 3 dashes of bitters.
• Add 1 cup of ice and blend until smooth.
• Pour the mixture into a glass and garnish with an orange wedge and a cherry.

Making Brown Sugar Syrup:

• In a small pot, combine 1 cup of brown sugar and 1 cup of water.
• Heat over medium heat until the sugar is completely dissolved.
• If the cocktail mixture is too thick, gradually add water (1 ounce at a time) until you achieve the desired consistency.