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Place rack in center of oven and preheat oven to 375°. Grease a baking sheet with vegetable oil. Place 2 butternut squash (about 4¾ lb. total), halved lengthwise, seeds removed, cut side down, on prepared sheet. Bake until squash is very soft, about 50 minutes. Using a paring knife, remove peel from squash; discard peel. Cut squash into 2" pieces.
Heat 2 Tbsp. vegetable oil on the stovetop in a heavy large pot over medium-low heat. Mix in 2 cups thinly sliced onion, 1 Tbsp. light brown sugar, 2 tsp. minced fresh ginger, 2 garlic cloves, coarsely chopped, and ½ cinnamon stick. Cover pot and cook until onion is tender, about 15 minutes. Add squash and 5 cups low-sodium chicken broth or vegetable stock and increase to medium-high heat. Bring to a boil, then reduce heat to medium-low. Cover and simmer 10 minutes. Discard cinnamon stick.
Working in batches, purée soup in a blender. Return soup to pot; season with kosher salt and freshly ground black pepper. Bring to a simmer, thinning soup with more broth if necessary.
Ladle soup into bowls. Top with chopped fresh parsley. Do ahead: Soup, without parsley, can be made 1 day ahead. Transfer to an airtight container and chill.
Editor’s note: Head this way for more of our favorite butternut squash recipes →