Prepare pie crust according to package directions. Divide into 6 equal portions, roll into balls and refrigerate covered for at least 1 hour. On a lightly floured surface, roll each into a circle about 1/4-inch thick.
Place each of the rolled out circles onto the baking sheet. Divide cherry pie filling into the center of each of the 6 pie crusts and sprinkle each with the pumpkin pie spice. Fold the edges of the pie dough over the cherry pie filling, making sure to leave the center of the pie exposed. Place a few of the reserved blueberries on top of each pie. Brush the sides of the pies with milk and sprinkle with 2 teaspoons of the sugar. Place pies in the oven and bake for 30 minutes, or until crust is golden brown and filling is bubbling. Remove from oven and allow to cool slightly.
For Blueberry Topping:
In a medium sauce pan over medium heat, stir together blueberries, sugar, and two tablespoons water. Bring to a boil, reduce heat and simmer for 10 minutes. Turn off the heat and allow to cool to room temperature.
To serve, place 1 warm pie on 6 plates, top each pie with a scoop of vanilla ice cream and a generous drizzle of the blueberry sauce.