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Preheat oven to 350°F. Cut squash in half lengthwise; remove and discard seeds. Arrange squash, cut-sides down, in 3-quart rectangular baking dish. Bake for 45 to 60 minutes, or until tender. Remove from oven; cool slightly. Scoop pulp from squash halves. Place cooked pulp in a bowl; mash with a potato masher or fork (you should have about 2 cups pulp).
Meanwhile, heat oil in a saucepan. Add onion; sauté for 5 minutes or until tender. Stir in broth, apples and maple syrup. Bring to a boil, reduce heat. Simmer, covered, for 20 minutes or until apple is very tender. Remove from heat. Cool slightly. Stir in mashed squash.
Transfer half the squash mixture to a blender (or one-fourth the mixture to a food processor). Cover; blend (or process) until smooth. Repeat with remaining mixture.
Return the blended squash mixture to the saucepan. Stir in whipping cream (if necessary, add additional broth to reach desired consistency); heat through. Season to taste with salt and pepper. Sprinkle each serving with chopped apple.