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Preheat the oven to 425°F with the rack in the middle.
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Place the squash halves cut-side up on a baking sheet. Brush olive oil over the tops and insides of the squash. Season with salt and pepper. Roast until tender, about 50 minutes to 1 hour.
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While the squash is cooking, peel, core, and cut the apples and potatoes into medium dice. Cut onion into medium dice. In a Dutch oven or large pot over medium heat, add the olive and saute the apple, onion, and garlic, season with salt, stirring occasionally, until mostly softened, about 5 minutes.
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When tender, remove squash from oven, set aside and allow to cool.
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Add the broth, water, potatoes and cinnamon stick, and bring to a boil over medium-high heat. Reduce the heat to medium low and simmer, stirring occasionally and potatoes are soft, about 15-20 minutes. Remove the pot from the heat and take out the cinnamon stick. Scoop the squash out of skins into the rest of the ingredients. Discard the skins.
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Using an immersion blender or regular blender (processing in batches), puree the mixture until smooth.
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Serve with maple syrup drizzled on top and garnish with pomegranate seeds.