Put the pitted cherries into a cocktail shaker and muddle.
Add the bourbon, cherry brandy, simple syrup, orange bitters and ice to the shaker and shake well until container is cold.
Fill two low-ball glasses half full with ice.
Pour shaken cocktail (plus the ice and muddled cherries) into your glasses.
Top with club soda.
Garnish with the whole cherries.
Notes
Want to try this cocktail outside of cherry season? You can use frozen cherries but I prefer the ease of using a good Cherry Jam. You'll probably need less simple syrup since the jam will be sweetened.