1 (4-pound) sugar baby pumpkin cut in half and seeds removed
1 tablespoon olive oil
Freshly ground black pepper
1/2 cup small-dice bacon (about 3 slices)
1/2 cup small-dice shallots (about 2 medium)
1/4 cup dry (fino) sherry
2 cups low-sodium chicken broth
2 cups water
1 1/2 teaspoons finely chopped fresh thyme leaves
1/4 cup heavy cream
Parsley Croutons, for garnish (optional)
Heat the oven to 375°F and arrange a rack in the middle. Rub the cut halves of the pumpkin with 1 tablespoon of the oil, and season generously with salt and pepper. Place on a baking sheet, cut side up, and roast until fragrant, tender when pierced with a fork, and golden brown, about 70 minutes. Remove from the oven and let sit on the baking sheet until cool enough to handle, about 20 minutes.
Using a large spoon, scoop out the flesh, place it in a medium bowl (you should have about 3 cups), and set it aside.
Place the bacon in a large, heavy-bottomed saucepan or Dutch oven over medium heat and cook until crispy and the fat is rendered, about 10 minutes. Remove with a slotted spoon to a small paper-towel-lined plate; reserve for garnish.
Add shallots to the bacon fat, season with salt and pepper, and sauté until softened, about 4 minutes. Add sherry and cook until reduced by half, about 2 minutes. Add chicken broth, water, thyme, and reserved pumpkin and season with salt and pepper. Stir to combine, then bring to a simmer.
Reduce heat to low and simmer until flavors have melded, about 10 minutes. Using a blender, purée the soup in batches until smooth, removing the small cap from the blender lid (the pour lid) and covering the space with a kitchen towel (this allows steam from the hot soup to escape and prevents the blender lid from popping off). Place the blended soup in a clean saucepan. Stir in the cream and season with salt and pepper as needed. Serve garnished with the reserved bacon and croutons, if using.
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