Blending the Ingredients: Combine ice cream, milk, pumpkin puree, pumpkin spice, and vanilla in a blender. Blend until smooth.
Preparing the Milkshake: Drizzle the inside of a pint glass (or another tall glass) with caramel. Pour milkshake into the glass, then top with whipped cream and more caramel. Garnish with a cinnamon stick, if desired.