1. Preheat oven to 400°.
2. Combine squash, 2 tablespoons oil, syrup, garam masala, salt, and pepper. Arrange squash mixture in a single layer on a jelly-roll pan coated with cooking spray. Bake at 400° for 45 minutes or until squash is tender.
3. Heat remaining 1 tablespoon oil in a large skillet over medium-high heat. Add shallots to pan; sauté 2 minutes or until tender. Stir in apple; sauté 4 minutes or until tender. Stir in wine; cook 1 minute. Stir in squash mixture, 3 cups water, and broth. Bring to a simmer; cook 3 minutes. Place half of squash mixture in a blender. Remove center piece of blender lid (to allow steam to escape); secure blender lid on blender. Place a clean towel over opening in blender lid (to avoid splatters). Blend until smooth. Strain squash mixture through a sieve into a bowl; discard solids. Repeat procedure with remaining squash mixture. Stir in half-and-half.
Wine note: This squash soup has a unique spicy-sweet flavor, thanks to the garam masala and maple syrup. It pairs exceptionally well with an aromatic white wine like viognier. Yalumba's Eden Valley Viognier 2007 (Eden Valley, Australia) is fantastic, with lively lime and ginger aromas and a clean, pure flavor, all for about $12. —Karen MacNeil