1.Peel and dice the winter melon and place into a pot. Sprinkle with brown sugar, mix well, and allow to sit for 1 hour. Turn pot on medium heat and bring to a boil.
2.Sprinkle with rock sugar, reduce heat and simmer for 20-30 minutes while stirring every 5 minutes to prevent the winter melon from burning. Once cooked the winter melon will be translucent and the juices will have thickened.
3.Remove from the heat and place the winter melon and juices into a food processor and blitz until smooth. Strain the winter melon pureé, set aside and allow it to cool.
4.Meanwhile simmer water, remove from the heat and add the tea bags, steep for 5 minutes. Remove the tea bags and allow the tea to come to room temperature.
5.While the tea is cooling bring a small pot of water to a boil, add the tapioca pearls, reduce heat and simmer for 5-6 minutes. Strain the pearls, add to a small bowl, and stir through the maple syrup. Set aside and allow to cool.
6.Evenly divide the soaked tapioca pearls and syrup between four glasses. Divide the ice between the glasses, top with the winter melon syrup, tea, and milk. Serve immediately.