Add apple cider, 2 tablespoons of brown sugar, orange zest, cinnamon sticks, and allspice to a pot over medium heat and bring to a simmer. Reduce heat to low and simmer for 30 minutes.
2 cups apple cider, 2 tablespoons light brown sugar, 1 orange, 4 cinnamon sticks, 1 teaspoon ground allspice
Remove the pot from heat and strain the liquid through a fine mesh sieve into a heat-safe jar. Allow it to cool to room temperature for about 1 hour.
Add ice to a shaker, then add the spiced cider, bourbon, and lemon juice. Close the shaker lid and shake vigorously for at least 30 seconds. Set aside.
1 cup ice, 4 ounces bourbon, ¼ cup lemon juice
On a plate, mix the remainder of the brown sugar with the ground cinnamon. Rim a glass with a bit of the spiced cider, then dip the rim in the cinnamon sugar mixture.
2 teaspoons ground cinnamon, 2 tablespoons light brown sugar
Pour the apple cider bourbon cocktail into the rimmed glasses. Garnish with apple slices and cinnamon sticks and serve immediately.
apple slices, cinnamon sticks, rosemary