1. Preheat oven to 375° F. Cut ends off squash. Split into 4 pieces. Rub with 2 tablespoons olive oil. Place flesh-side down on a baking sheet. Cook for 30 to 45 minutes or until tender. When cool enough to handle, scoop flesh into a bowl; set aside.
2. In a large pot, add remaining oil over medium heat. Add onions. Sauté until soft, about 5 to 7 minutes. Add garlic. Sauté for 1 minute. Add squash; stir to combine. Stir in the wine. Let reduce by half. 
3. Add 2 cups broth. Using an immersion blender, puree soup until smooth. Stir in remaining broth. Bring to a simmer. Add more broth for desired consistency. Taste for seasoning. Add salt and pepper, as needed. Turn off heat. Stir in the milk or cream. Garnish as desired.

Calories: 183, Fat: 10 g (2 g Saturated Fat), Cholesterol: 2 mg, Sodium: 450 mg, Carbohydrates: 21 g, Fiber: 3 g, Protein: 5 g.