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Preheat oven to 400°F.
Use 2 tbsp of olive oil to coat insides of the butternut and acorn quashes. Lay face down on sheet pan and place in preheated oven for about 30-40 minutes or until tender. Use remaining 2 tbsp olive oil to sauté carrots, celery and onion in a medium-sized stock pot over medium heat, until tender. Add garlic cayenne pepper and salt and pepper to taste, and sauté an additional 2-3 minutes. Remove squash from oven and let cool. The squash can be roasted and cooled overnight or well in advance of the soup preparation.
Scoop meat from squash and add to pot with vegetables. Add vegetable broth and bring to a boil. Reduce heat, cover and simmer for 30 minutes. When vegetables are very tender, use an immersion blender or food processer to puree the soup. Add coconut milk to the pureed soup, stir to blend and return to heat until ready to serve. Season with more salt and pepper if needed. Place the toppings in small serving bowls on the table and allow guests to garnish their soup.
Serving Tip: If desired, you can serve soup in small winter squashes or pumpkins. To prepare them, simply slice off the tops, scoop out the flesh, sprinkle insides with a bit of salt and pepper, and roast in a 400°F oven for about 20-35 minutes or until tender
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