Preheat oven to 375º.
Using a mixer, combine pumpkin, cream cheese, maple syrup, cinnamon, pumpkin pie spice, and vanilla until well mixed. Set aside.
Spread pie dough and using a 5-inch round cutter make the circles.
Whisk together whipping cream, maple syrup, and cinnamon.
Taking a round piece of dough, place about 3 tablespoons of filling in the center and fold the dough over to create a half-moon shape. Brush edges with whipping cream mixture.
Using fork tines, seal edges of the pastry.
Place pies on a parchment-lined baking sheet.
Brush top with whipping cream mixture.
Bake 16-20 minutes, until bottoms are golden brown. Let cool 30 minutes.
Make the icing by whisking to combine the cream cheese, powdered sugar, and milk. Drizzle over pies. Serve.