Adapted from foodnetwork.com.
- 3 whole acorn squash, approximately 8 cups when cooked
- 6 shallots, 3 diced, 3 left whole and peeled
- 6 cloves garlic, peeled
- 3 Tablespoons olive oil
- 1 Tablespoon Kosher salt
- 1 Tablespoon freshly cracked pepper, plus more for seasoning
- 2 Tablespoons butter
- 4 cups low- or no-sodium vegetable stock ( I like Kitchen Basics brand unsalted) or chicken stock
- 1/4 teaspoon cayenne pepper
- 1/4 teaspoon white pepper
- 1 teaspoon dried “rubbed” sage
- 3/4 cup heavy cream or half-and-half
- 1 Tablespoon Worcestershire sauce
- 1/4 cup grated parmesan
- Optional toppings: Black pepper, Drizzle of olive oil, French fried onions, pepitas, additional grated Parmesan
Preheat oven to 350 degrees. Cut the squash in half, on the equator, and remove seeds with a spoon. Cut a flat spot on each end, so the squash will sit still. Line a baking sheet with foil and arrange the squash, cut side up, on the baking sheet. To 3 of the squash halves, add a peeled shallot. To the other 3, add 2 garlic cloves in each. Drizzle with 2 tablespoons olive oil and season with salt and pepper. Roast in the hot oven until very tender and starting to caramelize and collapse, about 1 hour. Remove from oven and allow to cool. When cool enough to handle, remove the squash from the skin. Discard skin. Reserve the roasted shallots and garlic with the squash. All of the preceding steps may be done ahead.
In a large Dutch oven or soup pot, heat 1 Tablespoon of olive oil and 2 Tablespoons butter over medium-high heat. When the butter starts to foam, add the raw diced shallots and sauté until the start to caramelize, about 5 to 6 minutes.
Deglaze the pan with 1/2 cup of the stock and stir to detach bits of onion from the pan. Reduce the heat to medium-low and add the reserved squash, roasted shallots and garlic and then the remaining stock. Stir to combine, then puree with a stick blender. The mixture will be very thick.
Add the cayenne, white pepper, and sage. Stir in the cream and Worcestershire sauce and heat slowly over medium-low heat, stirring frequently. When the mixture comes to a slow simmer, stir in the Parmesan and turn heat to low. Serve with topping(s) if desired.
Serves 8-10.