In the bowl of a stand mixer (or electric mixer), add cream cheese, vanilla, and sugar; mix until completely smooth and combined. Add pumpkin puree, cinnamon, nutmeg, and salt; mix to combine completely.
Arrange a workstation with a small bowl of water, your wonton wrappers, and pumpkin filling. Working one at a time, add about 1 tbsp of pumpkin filling to the centre of your wonton, then using your finger, wipe water across all sides of the wonton. Bring one corner up to the other in the centre, and press together to seal. Then bring up the other 2 corners, and run your finger along to seal all edges. Set aside and repeat for all wontons.
In a large stockpot, add about cup of oil (should be about 1-2 inches deep). Heat over medium high heat, and when you see ripples the oil is ready. Carefully drop the wontons bottom side down into the oil and cook for about 1-2 minutes on the first side. When they start browning, use a spatula and flip over. Cook another 1-2 minutes or until crispy. Remove from oil and set on a paper towel lined plate. Repeat until all wontons are fried.
In a small bowl, add powdered sugar, maple syrup, and milk; mix together with a fork until smooth. Add more milk to loosen glaze if desired. Drizzle glaze over the tops of the wontons.