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Do you prefer a smooth soup or one with chunks? What really makes the difference is the base broth - use a good vegetable broth or even chicken broth if you want more body, not just water. Add your roasted or cooked squash to it, then blend it however you like. The thing people often forget: a pinch of nutmeg or fresh ginger is magic for bringing out the sweet flavors of the squash.
Don't boil your squash too long, you'll lose the flavor and it'll turn into bland mush. Cut your squash into chunks, roast it in the oven with a bit of oil and salt for about twenty minutes until it's really tender and lightly caramelized. Then blend everything with some good hot broth (vegetable or chicken), add cream or milk depending on what you like, taste it and adjust the seasoning. The real trick is roasting it in the oven first instead of cooking it on the stove - it concentrates the natural flavors and gives it a depth you don't get any other way.
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