Preheat the oven to 375°F and lightly coat a standard muffin tin with nonstick cooking spray. Unroll each crescent roll dough triangle and place them individually into the muffin cups, ensuring the widest part is positioned at the bottom. Generously spoon approximately 3 to 4 heaping tablespoons of cherry pie filling into each piece of dough, allowing for a little overflow if necessary. Carefully fold the three points of the dough over the filling to enclose it as much as possible. Bake the bites in the preheated oven for 13 to 14 minutes until the tops are golden brown and firm to the touch. Meanwhile, combine powdered sugar and milk in a bowl, whisking until the glaze is smooth and reaches a drizzling consistency. Once baked, remove the bites from the oven and immediately drizzle them with the prepared icing using a spoon.