In a large sauce pan over medium heat, add in the pumpkin, sugar, cinnamon, nutmeg, and cloves.
Stir until well combined. Add in the vanilla and stir.
Add in the whole milk and then whisk until well combined.
Use an immersion blender to blend up the mixture and add some froth OR very carefully transfer the mixture to a blender and pulse a few times to get that good frothy texture.
Fill up glasses with ice cream and then add in the pumpkin spice drink.
Top with spray whip topping and caramel dessert topping as desired.