Preheat oven to 400°.
Combine squash, 2 tablespoons oil, syrup, salt, garam masala, and pepper in a large bowl. Arrange squash in a single layer on a jelly-roll pan coated with cooking spray. Bake at 400° for 45 minutes or until soft.
Heat remaining 1 tablespoon oil in a large skillet over medium-high heat. Add shallots; sauté 2 minutes or until tender. Stir in apple; sauté 2 minutes or until tender. Stir in wine; cook 1 minute. Stir in squash, water, and broth. Bring to a simmer; cook 3 minutes. Place half of soup in a blender; process until smooth. Strain mixture through a sieve into a bowl; discard solids. Repeat procedure with remaining half of soup. Stir in soy milk.