1. To make the cranberry simple syrup: In a medium saucepan over medium-high heat, bring all simple syrup ingredients to a boil, stirring occasionally. Reduce heat to a simmer; cook, stirring occasionally, for 10 minutes or until sugar is dissolved, cranberries have burst and mixture is very slightly thick and red in color. Remove from heat; steep mixture for another 10 minutes, then use a fine-mesh sieve to strain syrup into a jar with a tight-fitting lid. Cool completely at room temperature, then store in refrigerator for up to 2 weeks.

2. To make one cocktail: Add bourbon, cranberry simple syrup and bitters to a cocktail glass; stir for 10 to 15 seconds, then top off with ice. Garnish with fresh cranberries and a twist of orange.