Make the syrup: In a medium size saucepan, combine the ingredients. Heat over medium heat, stirring until combined.
Bring to a slow boil, reduce the heat and simmer for 5 minutes – stirring occasionally. Let cool 5 minutes before using.
Make the cocktail: In a short tumbler glass, muddle the orange slice and cherry until lightly smashed. Pour in the gingerbread syrup and bourbon. Fill the glass ¾ of the way with crushed or cubed ice. Stir with a cocktail spoon until all the syrup and bourbon have combined, about 10 to 15 seconds.
Optional: Using a vegetable peeler, peel a piece of orange zest. Heat the outside of the zest with a lighter for 1 to 2 seconds then rub on the lip of the glass. Garnish with a fresh candied cherry.