In a cocktail shaker filled with ice, add 1½ oz rye whisky, ½ oz lemon juice, ½ oz cinnamon simple syrup, 1 oz apple juice and 2 oz pomegranate juice. Shake and strain into a rocks glass with ice and garnish with an apple fan.
Combine sugar, water, and cinnamon sticks in a small saucepan over medium heat. Bring to a simmer, stirring occasionally, until sugar is dissolved. Remove from heat and let sit at room temperature overnight.
Remove cinnamon sticks and store syrup in an airtight container in the fridge for up to two weeks.