Divide the orange juice, red wine, and brandy evenly between two large wine glasses.
Add a slice of orange and a cinnamon stick to each glass.
Divide the chopped apple and cranberries evenly between the two glasses.
Stir briefly to combine.
Refrigerator for at least one hour.
Add sugar to a shallow dish with a wide mouth.
Briefly rinse rosemary sprigs under water, shaking excess water off.
Roll the rosemary sprigs in sugar. Set aside on a clean plate until ready to garnish.
Serve chilled or at room temperature.