In a large sauce pan over medium heat, add in 1 cup canned pumpkin puree , ½ cup packed light brown sugar,1 teaspoon cinnamon, and pinch of each: nutmeg and ground cloves. Stir until well combined. Add in the vanilla and stir.
Add in 1 tablespoon vanilla extract and stir. Add in 4 cups whole milk and whisk until 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 coffee flavored ice cream and then add in the pumpkin spice drink.
Top with spray whipped topping and caramel dessert topping as desired.