In a large dutch oven, heat Olive Oil (1 tablespoon) over medium heat. Add the Apple (3), Onion (1), Carrot (2), and Kosher Salt (1/2 teaspoon).
Saute until softened and onions are slightly translucent (do not brown, adjust heat lower if vegetables start to take on color). Add the Ground Cinnamon (1/2 teaspoon) and Ground Nutmeg (1/4 teaspoon) and cook for an additional minute or so until very fragrant.
Add the oven-roasted Butternut Squash (2 pound) and Vegetable Broth (6 cup). Heat just to boiling, then reduce heat to low and cover with the lid slightly askew. Simmer for 10 minutes.
Working in batches transfer the mixture to a blender and puree until smooth. If soup is too thick, add additional broth about half a cup at a time.
Return the soup to the dutch oven, and add the Heavy Cream (1/2 cup) and Calvados Apple Brandy (1/4 cup). Heat the soup over medium heat, stirring occasionally until it's hot. Taste and adjust seasoning if needed.