Combine the bourbon, syrup and bitters in a large glass and stir. Fill a glass with a large ice cube (or 6 regular ice cubes). Pour in the cocktail and stir. Squeeze the orange peel with the skin side down over the glass and drop into the cocktail. Add the cherry.
You can make a batch of this cocktail by multiplying the ingredients by the number of people you're serving and mixing everything in a large pitcher.