Preheat the oven to 425 degrees F and prepare a baking sheet with a sheet of parchment paper.
On a sheet of parchment paper, flatten or roll out the pie crust (depending on which kind you have). Cut into even rectangles with a knife, depending on which size of pop tart you want.
Place one half of each pop tart pastry onto the baking sheet, leaving room in between each one, like you would with cookies.
Place a row of jam in the very center of the pop tart and down the middle. Do not get the jam close to the sides.
Cover each pop tart with the other half of the pastry. Push down on the edges of each tart with your fingers, so the pastry squishes together. Then crimp the edges with a fork. Finally, poke 4-6 holes in the top of each pastry with a toothpick to let the steam escape when cooking.
Place the tarts in the oven to bake for 11-12 minutes.
Remove from the oven and let cool on a wire rack.
To make the icing, add the sifted powdered sugar to a large bowl. Add the vanilla and whole milk and stir until combined. Add the food coloring (optional) and stir. Drizzle the icing over the pop tarts, then let cool.