Pumpkin Soup with Grilled Cheese Croutons

Preheat an oven to 350°F (180°C). Line a baking sheet with parchment paper.

To make the soup, using a sharp knife, carefully cut off the top of each pumpkin to remove the stem, then halve each pumpkin vertically. Using a spoon, scoop out the seeds and any stringy fibers and discard. Brush the flesh of the pumpkins generously with olive oil, then place them, cut sides down, on the prepared baking sheet. Bake until the pumpkins are very tender when pricked with a fork, about 50 minutes. Let cool for 15 minutes, then scoop the flesh from the peel into a bowl; discard the peels. You should have about 4 cups of pumpkin. Set aside.

In a Dutch oven or large, heavy saucepan over medium heat, melt 3 Tbs. of the butter. Add the shallots and cook, stirring occasionally, until softened, about 5 minutes. Add the garlic and thyme and cook, stirring, until fragrant, 1 minute. Add the marsala and deglaze the pan, stirring to scrape up any bits on the bottom of the pot. Add the pumpkin and cook, stirring occasionally, until lightly browned, about 3 minutes. Add the broth and maple syrup. Bring to a simmer, then reduce the heat to low and simmer gently for 20 minutes. Stir in the half-and-half.

Using an immersion blender, blend the soup until smooth. (Alternatively, working in batches, transfer the soup to a blender and puree until smooth. Pour back into the pot.) Add the remaining 3 Tbs. butter to the soup and stir until the butter is melted. Season the soup with salt and pepper. Stir in more vegetable broth, if desired, to achieve the desired consistency. Keep warm over low heat while you make the grilled cheese croutons.

To make grilled cheese croutons, spread the butter on one side of each slice of bread, dividing it evenly.

Heat a large fry pan over medium heat. Place 3 slices of the bread, butter side down, in the fry pan. Divide the cheese evenly between the 3 slices in the pan, then top with remining bread slices, butter side up. Cook until the bottom of bread is golden brown, then carefully flip each sandwich and continue to cook until the cheese is melted, about 5 minutes, turning down the heat if the bread is browning too quickly.

Transfer the grilled cheese sandwiches to a cutting board and let cool slightly while you ladle the warm soup into 6 individual bowls. Drizzle each serving of soup lightly with olive oil and sprinkle with a few grinds of pepper. Cut the grilled cheese sandwiches into 1-inch (2.5-cm) cubes and divide them evenly among the bowls of soup. Garnish with thyme sprigs and serve immediately. Serves 6.

Williams Sonoma Test Kitchen