Preheat oven to 425˚F. Wash and dry the outside of the squash. Cut the squash in half lengthwise or through the middle (depending on the variety) and scoop out the seeds, leaving the stringy flesh in tact whenever possible. Then, slice the squash into 1 inch thick pieces. Note: Acorn squash skin easily peels off after being roasted. So don’t worry about removing it beforehand. If you’re using Delicata the skins are edible and will be left on entirely.
Place squash onto a large baking sheet or roasting pan (you may need two) and top with salt, pepper and two tablespoons olive oil. Place the pan on the upper rack of the oven and roast for about 30-40 minutes, turning the pan about halfway through. They’re done when fork tender and slightly caramelized.
While the squash is roasting, bring two tablespoons of olive oil to medium heat in a large dutch oven or stock pot. Once the oil is heated, toss the chopped onion, carrot, and celery into the pot. Allow to soften but not brown, about five minutes. Next, toss in the cinnamon sticks, anise, bay leaf and fresh sage, continue to cook for about 10 minutes, adjusting the heat lower so the mixture doesn’t brown or burn.
Remove the squash from the oven (when finished as noted above) and allow to cool slightly. At this point, it’s easy to peel away the skin from the acorn squash. Place the roasted squash into the stock pot. Add four cups of the stock (or water) to the mixture and bring to a simmer. Simmer for about 10 minutes while stirring and breaking up the squash with a wooden spoon.
Remove soup from heat and allow to cool slightly. Remove the bay leaf, cinnamon and star anise. Pour about 1/3 of the soup into a blender or food processor (or use an immersion blender if you have one). Puree in batches until all the soup is blended, use the remaining cup of stock as needed to reach the desired consistency while pureeing.
Pour the blended soup back into the stock pot and bring to heat. Taste and then season with salt and pepper as needed. Ladle the warmed soup into individual bowls, drizzle with maple cream and finish with reserved, chopped sage. Store in the refrigerator for 3 or 4 days, or freeze up to 6 months.
Be sure the cream cheese is softened by leaving it on the kitchen counter at room temperature for about 30 minutes.
In a mixing bowl, whisk the cream cheese with maple syrup and half the milk. Add milk slowly as needed to reach a creamy, sauce-like consistency that can be drizzled onto the soup. Store in the refrigerator for 3 to 4 days.