Place the maple sugar in a shallow bowl.Wet the rim of your martini glass, and then roll the rim in the maple sugar to create an even sugared rim. Set aside.
In a martini shaker filled with ice, add milk, vodka, creme de cocoa, maple syrup, and pumpkin puree.Shake well until pumpkin is fully blended.
Strain cocktail into your prepared martini glass.Garnish with a sprinkle of pumpkin pie spice and a cinnamon stick.