Make the vanilla fig simple syrup by combining the sugar, water, vanilla extract or paste, and dried figs in a saucepan over medium low heat.
Bring the mixture to a simmer. Gently smash the figs on the side of the pan to help infuse their flavor into the syrup. Stir to combine, then simmer for 5 minutes, or until the sugar completely dissolves.
Remove the pan from the heat and allow to cool to room temperature. Remove and discard the figs along with any other large pieces, or strain through a mesh colander.
In each old fashioned glass (or rocks glass) filled with ice, add 2 ounces (¼ cup) of bourbon, 3 dashes of angostura bitters, and 1 ounce (2 tablespoons) of vanilla fig simple syrup. Stir to combine.
Garnish each drink with a large orange peel and fresh fig, if available.
Notes
For best flavor, purchase good quality bourbon, but stay within your budget.
Angostura bitters can be found in the "cocktail mixer" aisle of your grocery store.
Dried figs can be found year-round near the nut and dried fruit aisle or salad toppings aisle of your local grocery store.
Adjust the sweetness of the cocktail by adding a small amount of the simple syrup to the drink at a time. Taste it, then adjust accordingly.