Add all ingredients in order listed to high speed blender. Add more or less ice and pumpkin pie spice for desired thickness and pumpkin pie flavor.
To cut the pumpkin, simply quarter it, keeping seeds intact. Then turn each quarter of the pumpkin on its side and cut off the skin (see photo). Use the same technique for a larger pumpkin and add ~1 cup of pumpkin (+seeds) to your smoothie.