Delicata squash, as its name implies, is a finely flavored, richly sweet winter squash with a nearly fibreless flesh. Cylindrical in shape, with elongated ridges, this squash has yellow to pale orange skin with green striations. Its beautiful yellow flesh and delicate flavor make it perfect for this puréed soup.
2 pounds delicata squash, halved lengthwise and seeded
2 tablespoons olive oil
2 (about 1 pound total) Granny Smith apples, halved lengthwise and cored
4 cups homemade chicken stock or canned low-sodium chicken broth
1/2 cup heavy (whipping) cream
1/4 teaspoon freshly grated nutmeg
1 tablespoon sugar
Salt and freshly ground pepper
2 cups French or rustic white bread 1/2-inch cubes, crusts removed
1 tablespoon olive oil
2 tablespoons grated Parmesan cheese
Preheat the oven to 350ºF. Brush the flesh of the squash with olive oil and place, cut side down, on a rimmed baking sheet. Place the apples, cut side down, on the baking sheet. Roast until tender when pierced with a fork, about 30 to 35 minutes.
Use a spoon to scrape out the flesh of the squash and apples, and put in the work bowl of a food processor fitted with the metal blade. Discard the skins. Purée until smooth. Add 1 cup of the stock and continue processing until smooth. Put this mixture in a 3½- to 4-quart saucepan, add the remaining 3 cups of stock, the cream, nutmeg, and sugar. Bring to a boil, and then reduce to a simmer and cook for 10 minutes. Add salt and pepper to taste.
To make the croutons: Place the bread cubes in a large mixing bowl. Drizzle the olive oil over, add the Parmesan, and toss the bread cubes until thoroughly coated. Spread in an even layer on a rimmed baking sheet and bake until toasty brown, about 10 to 12 minutes. Set aside until ready to serve.
When ready to serve, ladle the soup into a warmed soup tureen or individual soup bowls, garnish with the croutons, and serve immediately.
The soup can be made up to 3 days ahead. Cool and refrigerate, covered; rewarm just before serving. The croutons can be made 2 days in advance. Store in a covered container at room temperature.