Combine milk, maple syrup, pumpkin purée, vanilla, cinnamon, nutmeg, pumpkin pie spice, and ginger in a blender or food processor and pulse until smooth.
Stir in instant vanilla pudding. Cover and chill until thickened slightly.
Serve immediately, cold, or transfer to a sauce pan and heat until hot throughout. Top with 1/4 cup whipped cream and, if desired, 1 tablespoon caramel sauce. Garnish with additional pumpkin pie spice for serving and serve.