In a blender, combine pumpkin, soy milk, yogurt, pumpkin spice, juice of half a lemon, and 1 dash of vanilla extract. Blend together until smooth, and begin adding the ice while continuing to blend. When mixture is thick and creamy, stop and hold in refrigerator at least 30 minutes. Cut off the top 1/3 of the orange. Remove the inside of the orange and reserve the rind. In a medium mixing bowl, combine cream, powdered sugar, and the remaining vanilla extract; then whip on high until a stiff peak forms. Transfer the smoothie into the orange rind, and garnish with whipped cream and cinnamon sticks