Make the spiced syrup: Combine the sugar, 1/2 cup water, the allspice, star anise and ginger in a small saucepan. Bring to a boil, stirring occasionally to dissolve the sugar. Remove from the heat and let cool completely. Strain into a liquid measuring cup.
Make the cocktails: Combine the bourbon, apple cider, orange juice, lemon juice, 1 ounce of the spiced syrup (reserve the rest for more cocktails) and the orange bitters in a cocktail shaker. Fill with ice and shake vigorously until chilled, about 30 seconds. Strain into 2 ice-filled rocks glasses and top with the red wine. Garnish with cinnamon sticks.