Combine the bourbon, lemon juice, lime juice, and syrup in a pitcher. Fill a cocktail shaker two-thirds full with ice and fill halfway full with the cocktail mixture. Shake for 30 seconds and pour into a martini glass. Repeat as needed. Serve each drink ice cold with a skewer of cherries.
In a small bowl, combine the 1/2 cup dried cherries with 4 ounces of bourbon and microwave on high for 60 seconds. Set aside to cool. Thread 3 or 4 marinated cherries onto small skewers.
To make sugar syrup, combine 1 cup of sugar and 1 cup of water in a small saucepan and cook over medium heat until the sugar dissolves. Chill thoroughly before using.