Chef Stephanie Izard served this delicous, creamy soup at the 2011 CMT Artists of the Year dinner that she had the pleasure of catering. The menu for the event was created by her and inspired by the artists' — Kenny Chesney, Lady Antebellum, Taylor Swift, and others — favorite foods and flavors from the South.
This soup in particular was one of Taylor Swift's favorites.
Combine all of the ingredients in a small, heavy-bottomed, nonreactive saucepot. Bring to a boil and then reduce the heat to medium. Simmer the liquid to reduce until syrupy, about 20 minutes. Cool and strain out the thyme and peppercorns. Set aside until the soup is ready.
Preheat the oven to 375 degrees and set 2 racks evenly apart.
Scoop out the seeds from each squash half and put them in a small mixing bowl. Scrape out most of the stringy pulp from the squash and discard. Spread ½ teaspoon of the butter inside each squash half and then season them with salt and pepper, to taste. Place the squash halves cut side down in a baking dish large enough to hold all 4 (divide them between 2 baking dishes if they don’t fit in 1 dish). Add enough of the water to go ½ inch up each squash half.
Toss the squash seeds with 1 teaspoon of the olive oil and spread them out on a baking sheet. Transfer the squash and the seeds to the oven. Bake the seeds on the bottom rack for 15 minutes, or until they begin to brown. Remove from the oven, season with salt and set aside.
Put the squash on the top rack in the oven and bake them for about 45 minutes, or until the flesh is tender. Remove from the oven and set aside to cool. When the squash are cool enough to handle, scoop out the flesh and discard the skins. Reserve the squash flesh and baking liquid.
Heat a Dutch oven or large, heavy-bottomed saucepot over medium-low heat and add the remaining olive oil. Add the onion and garlic and sweat for 5 minutes. Add the apple and fennel, season with salt and pepper, to taste, and sweat for 15 more minutes. Add the white wine and simmer to reduce almost all of the liquid. Add 4 cups of chicken stock, the reserved liquid, and the pumpkin flesh. Bring to a boil, then reduce heat to a simmer and cook 1 ½ hours.
Meanwhile, slowly melt the remaining butter in a heavy-bottomed saucepot over medium heat. Continue past melting until the milk solids begin to fall to the bottom of the pot and start to brown. Take care not to let the solids blacken, removing the butter from the heat when it is dark brown, about 10-15 minutes. Strain through a fine mesh sieve and discard the solids.
Working in batches, ladle the soup mixture in the pot into a blender. Blend until smooth, stopping to loosen the ingredients with a wooden spoon, if necessary. Add additional chicken stock to thin the purée if it is too thick. Divide the brown butter and blend in with the first 2 batches. Season with salt and pepper, to taste. Ladle the soup into bowls, drizzle with sherry gastrique, and sprinkle with toasted squash seeds.