Place 1 orange half slice, 1 cherry, and ½ teaspoon sugar in each rocks glass. Muddle (see Notes) until the fruit is well mashed and mixed with the sugar
Fill the glasses with ice, pour over the bourbon, and stir well. Top off with soda, stir, and serve.
GLASSWARE: Rocks glasses
Muddling information: To muddle, place the fruit, herbs, sugar, or other ingredients to be muddled in the bottom of a large glass or shaker. Using the flat end of the muddler, firmly press and twist the tool, crushing and breaking down the fruit or herb to release as much juice and essential oil as possible. If bruising an herb, do not press quite as hard, for you do not want to pulverize it.