Heat 1/4 cup cream and 1/4 cup brown sugar in a saucepan over medium heat until mixture starts to boil. Raise heat to medium-high and stir in apple cider and water. Cook until mixture starts to simmer, about 4 minutes.
Beat 1/2 cup cream and 1 tablespoon brown sugar together in a bowl until soft peaks form. Lift your beater or whisk straight up: the whipping cream will form soft mounds rather than a sharp peak.
Pour cider into mugs and top with caramel whipped cream.