How to Make It
Peel and seed squash, reserving peels, trimmings, and seeds. Cube peeled and seeded squash. Heat a large Dutch oven over medium-high heat. Add 1 tablespoon oil; swirl to coat. Add squash scraps; sauté 8 minutes or until lightly browned. Add 7 cups water, allspice, and next 5 ingredients (through anise). Bring to a boil; cover, reduce heat, and simmer 45 minutes. Strain mixture into a large bowl; discard solids.
Wipe pan clean with paper towels; heat over medium heat. Add remaining 3 tablespoons oil and onion; cover and cook 5 minutes, stirring occasionally. Add cubed squash; cover and cook 10 minutes, stirring occasionally. Add reserved broth and salt; bring to a boil. Cover and simmer 40 minutes or until squash is very tender.
Place half of squash mixture in a blender. Remove center piece of blender lid (to allow steam to escape); secure blender lid on blender. Place a clean towel over opening in blender lid (to avoid splatters). Blend until smooth. Pour into a large bowl. Repeat procedure with remaining squash mixture. Stir in vinegar and red pepper. Ladle soup into shallow bowls. Top evenly with pomegranate and cilantro.
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Dovetail and Narcissa, both in New York