Cut acorn squash in half lengthwise and scoop out the seeds and strings.
Brush 1 tablespoon olive or coconut oil over the cut surface. Place squash cut side down in a glass or clay baking dish. Add water to cover the bottom of the pan (about ½ inch) and bake in preheated oven for 30 to 35 minutes, until tender. Discard water.
Heat the remaining olive or coconut oil in a large skillet and sauté the shallots for about 3 minutes, stirring until softened. Add the apple and cook about 3 minutes more, stirring until blended.
Add the cranberries, maple syrup or sugar, orange juice, cinnamon, salt, and pepper. Cover and cook about 5 minutes.
Spoon the stuffing into the squash cavities and bake uncovered 15 to 20 minutes more. Serve hot.
TIP: Fuji, Gala, Rome or Braeburn apples are good choices for this dish. Each serving contains 336 calories, 11g total fat, 1g saturated fat, 0g trans fat, 0mg cholesterol, 64g carbohydrate, 302mg sodium, 5g fiber, 3g protein