Ingredients

• 3 whole acorn squash, approximately 8 cups when cooked
• 6 shallots, 1 cup diced, 3 left whole and peeled
• 6 garlic cloves, peeled
• 3 tablespoons olive oil, plus 1/3 cup extra-virgin olive oil
• 1 tablespoon salt
• 1 tablespoon pepper, freshly cracked, plus more for seasoning
• 1 stick unsalted butter, in all
• 4 cups chicken stock, low-sodium
• 1/4 teaspoon cayenne
• 1/4 teaspoon white pepper
• 1 teaspoon sage, dry
• 1 teaspoon savory
• 1 cup heavy cream
• 1 tablespoon Worcestershire sauce
• 1/3 cup grated Parmesan

Instructions

1. Watch how to make this recipe.
2. Preheat the oven to 350 degrees F. Cut the squash in half on the equator and remove the seeds with a spoon. Cut a flat spot on each end so the squash will sit flat. Line a baking sheet with aluminum foil and arrange the squash, cut side up. To 3 of the squash halves, add a peeled shallot and to the other 3 add 2 garlic cloves on each. Drizzle with 2 tablespoons of olive oil and season with 1 tablespoon each of the salt and freshly cracked pepper. Roast in the hot oven until very tender and starting to caramelize and collapse, approximately 1 hour. Remove from oven and when cool enough to handle, remove the squash from the skin. Reserve the roasted shallots and garlic with the squash. Can be done ahead.
3. 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. Deglaze with 1/2 cup of the chicken stock and stir to remove any fond. Reduce the heat to medium-low and add in the reserved squash, roasted shallots and garlic and then the remaining chicken stock. Stir to combine, then puree with a stick blender. The mixture will be very thick. Add in the cayenne, white pepper and the herbs. Stir in the cream and Worcestershire sauce and heat slowly over medium-low heat. 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. Serve with a fresh crack of black pepper, a nice drizzle of extra-virgin olive oil and a light sprinkle of remaining Parmesan. Ladle into soup bowls and serve.