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1. Place prunes in a small bowl and add boiling water to cover. Let stand 5 minutes; drain. Return prunes to bowl and stir in 2 tablespoons Calvados. Cover with plastic wrap and reserve until ready to use.
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2. In a large skillet, melt 4 tablespoons butter over medium-high heat. Stir in sugar, 1/4 teaspoon salt, 1/4 teaspoon pepper and 1/8 teaspoon nutmeg. Add chestnuts and cook, stirring occasionally to coat chestnuts with butter mixture, until chestnuts are golden and caramelized, 3 to 4 minutes. Stir in remaining 2 tablespoons Calvados and cook, scraping up any browned bits from bottom of skillet, until liquid is mostly evaporated. Remove chestnuts from heat.
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3. In a large pot, melt remaining 2 tablespoons butter over medium-high heat. Stir in the celery, carrots, shallots and leek; cook, stirring, until softened, about 5 minutes.
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4. Stir in chestnuts, apples, stock and remaining 1 teaspoon salt and 1/2 teaspoon pepper. Tie thyme and parsley together with kitchen twine and add to pot. Bring mixture to boil; reduce heat to medium-low and simmer, uncovered, until vegetables are very tender, 25 to 30 minutes. Remove herbs and discard.
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5. Puree soup in batches in a food processor or blender (or use an immersion blender). Return soup to pot. Stir in 1/2 cup heavy cream. Keep soup warm over low heat.
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6. With an electric mixer, beat remaining 1/2 cup cream with remaining 1/8 teaspoon nutmeg until cream forms soft peaks.
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7. To serve, place a prune in each bowl. Fill each bowl with a ladleful of soup. Top with a dollop of whipped cream and drizzle with Calvados.
