In a large bowl, combine the squash, 2 tablespoons oil, syrup, salt, garam masala, and pepper. On a rimmed baking sheet lined with parchment paper or sprayed with nonstick spray, arrange the squash in a single layer. Bake for 45 minutes or until soft.
In a large skillet over medium heat, heat the remaining 1 tablespoon oil. Add the shallots; sauté 2 minutes or until tender. Stir in the apple; sauté 2 minutes or until tender. Stir in the wine; cook 1 minute. Stir in the squash, water, and broth. Bring to a simmer; cook 3 minutes.
Place half of the soup in a blender or food processor; process until smooth. Repeat the procedure with the remaining half of the soup. Stir in the milk and serve.
Notes
If you do not have the spice Garam Masala on hand, you can make your own from a blend of spices: Mix ½ tablespoon ground cumin, ¾ teaspoon ground coriander, ¾ teaspoon ground cardamom, ¾ teaspoon ground pepper, ½ teaspoon ground cinnamon, ¼ teaspoon ground cloves, ¼ teaspoon ground nutmeg. This makes about 2 tablespoons of garam masala, so you'll have some to keep for later.
When you process the soup, if you're processing it while it's hot, be careful. Keep the hole off the top of the blender or food processor open so steam has a chance to escape.
If preparing this recipe as GLUTEN-FREE, just be sure to use brands of maple syrup and chicken broth that are known to be GF.
Weight Watchers Points do NOT include the optional drizzle of heavy cream or toasted pepitas.