Combine the milk, vanilla, and cinnamon in a heavy pot. Slowly bring the mixture just to the boil over medium heat, being careful not to scorch the milk. Reduce the heat to low, add the rice, and cook at a low simmer for 1 hour, uncovered and stirring occasionally, or until the rice is thoroughly cooked and creamy. Remove from the heat. Stir in the cherries and the sugar and cool as quickly as possible. Refrigerate until completely cold.
Whip the heavy cream into stiff peaks with an electric mixer. Using a spatula, fold the cream into the chilled pudding, spoon into pudding cups, and serve immediately or refrigerate until needed.