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1
Heat the oven to 375 degrees F and arrange a rack in the middle.
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2
Rub the cut halves of the pumpkin with the oil and season generously with salt and pepper.
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3
Place on a baking sheet cut-side up and roast until fragrant, tender when pierced with a fork, and golden brown, about 70 minutes.
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4
Remove from the oven and let sit on the baking sheet until cool enough to handle, about 20 minutes.
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5
Using a large spoon, scoop out the flesh, place it in a medium bowl (you should have about 3 cups), and set it aside.
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6
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.
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7
Remove with a slotted spoon to a small paper-towel-lined plate and set aside.
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8
Add the shallots to the bacon fat, season with salt and pepper, and saute until softened, about 4 minutes.
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9
Add the sherry and cook until reduced by half, about 2 minutes.
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10
Add the stock or broth, water, thyme, and reserved pumpkin and season with salt and pepper.
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11
Stir to combine, then bring to a simmer.
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12
Reduce the heat to low and simmer until the flavors have melded, about 10 minutes.
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13
Using a blender, puree 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).
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14
Place the blended soup in a clean saucepan.
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15
Stir in the cream and season with salt and pepper as needed.
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16
Serve garnished with the reserved bacon and the croutons, if using.