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1
Preheat the oven to 350 degrees F. Cut the squash in half on the equator and remove the seeds with a spoon.
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2
Cut a flat spot on each end so the squash will sit flat.
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3
Line a baking sheet with aluminum foil and arrange the squash, cut side up.
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4
To 3 of the squash halves, add a peeled shallot and to the other 3 add 2 garlic cloves on each.
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5
Drizzle with 2 tablespoons of olive oil and season with 1 tablespoon each of the salt and freshly cracked pepper.
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6
Roast in the hot oven until very tender and starting to caramelize and collapse, approximately 1 hour.
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7
Remove from oven and when cool enough to handle, remove the squash from the skin.
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8
Reserve the roasted shallots and garlic with the squash.
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9
Can be done ahead.
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10
In a large Dutch oven, heat 1 tablespoon of the olive oil and 2 tablespoons of the butter over medium-high heat and when the butter is starting to foam, add the raw diced shallots and saute until they are starting to caramelize, about 5 to 6 minutes.
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11
Deglaze with 1/2 cup of the chicken stock and stir to remove any fond.
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12
Reduce the heat to medium-low and add in the reserved squash, roasted shallots and garlic and then the remaining chicken stock.
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13
Stir to combine, then puree with a stick blender.
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14
The mixture will be very thick.
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15
Add in the cayenne, white pepper and the herbs.
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16
Stir in the cream and Worcestershire sauce and heat slowly over medium-low heat.
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17
When the mixture comes to a slow simmer, mix again with the stick blender and stir in 1/4 cup of the Parmesan and turn heat to low.
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18
Serve with a fresh crack of black pepper, a nice drizzle of extra-virgin olive oil and a light sprinkle of remaining Parmesan.
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19
Ladle into soup bowls and serve.
