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Preheat oven to 350°F. Lightly grease a 2-1/2- to 3-quart baking dish. In a large skillet, cook bacon over medium-high heat until crisp. Using a slotted spoon, remove bacon from pan and drain on paper towels; crumble and set aside. Reserve 1 tablespoon of the drippings in the pan; discard the remaining drippings. Add onions, celery and red pepper to drippings in pan; cook and stir over medium heat for about 5 minutes or just until vegetables are tender. Transfer vegetables to a 4- to 5-quart Dutch oven.
Add 4 1/2 cups chicken broth and the wine to the pot; bring to a boil. Add barley. Return to boiling; reduce heat. Simmer, covered, for 25 minutes. Stir in squash. Cook, covered, about 20 minutes more or until squash and barley are tender, stirring occasionally. Remove from heat. Stir in crumbled bacon, sage, salt and pepper; mix well. Spoon into the prepared baking dish.
If desired, drizzle dressing with an additional 1/4 cup chicken broth to moisten. Bake, covered, for 45 to 55 minutes or until heated through, stirring once. If desired, top with fresh sage leaves.