Preheat the oven to 400°F.
Cut your squash in half lengthwise and scoop out the seeds. Place it cut side down in a roasting pan that has been sprayed with nonstick spray and bake for 40-45 minutes or until very tender. Set aside until it’s cool enough to handle. (You can cook the squash up to 2 days in advance; keep it covered in the fridge until you need it.)
Heat the oil in a large saucepan set over medium heat and sauté the onion until soft. Add the curry powder, pear, ginger and garlic and cook for a few more minutes, until the pear starts to soften. Peel the skin off the cooked squash using a vegetable peeler, paring knife or your fingers, and cut it into rough chunks. Add it to the soup with the chicken stock and bring it to a simmer. Reduce the heat and cook for about 10 minutes.
Purée the soup in a blender, or use a hand-held immersion blender to purée it right in the pot until it’s as chunky or as smooth as you like. Return the soup to the stovetop, add the milk or cream (if using), season with salt and pepper, and stir just until it’s heated through.
Serving Size Serves 4-6.