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1. Preheat oven to 425 F.
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2. Cut each acorn squash into wedges, remove seeds and membranes and place skin side down in a large shallow baking pan. Bake at 425 F for approximately 30-45 minutes or until squash is tender when pierced with a fork. Remove squash from oven and let cool to the touch.
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3. When squash is cool enough to handle, scoop the flesh from the skin and into a saucepan. Scrape any liquid and caramelized squash juices that remain in the baking dish into the saucepan as well.
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4. Peel and core the pears. Cut into chunks and add to the squash. Add the ginger.
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5. Add 2 cups of water, 1/2 teaspoon salt, ground black pepper and heat the squash mixture on the stove over medium-high heat until it begins to boil, stirring occasionally. Lower heat to medium-low and simmer for 20 minutes, stirring occasionally.
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6. Remove from heat. Working in batches if necessary, spoon squash mixture into a food processor or blender and process until smooth. Pour soup into a heat-proof bowl as you process the next batch.
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7. When all squash mixture is processed and smooth, pour it back into the saucepan and add the brown sugar. Heat the soup again until hot, adding additional water if necessary for desired consistency. I often end up adding another cup of water at this point. Check for seasoning, adding salt and pepper, if necessary. Serve hot.
