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Step 1
Preheat oven to 400°. Arrange bacon strips in a single layer in a 15x10x1-in. baking pan. Bake until crisp, 15-18 minutes. Remove bacon to paper towels to drain, reserving drippings in pan. Add bread cubes to dripping; toss to coat. Bake until lightly browned, 6-8 minutes, turning occasionally.
Step 2
In a large skillet, melt butter over medium-high heat. Add onion; cook and stir until softened, 3-5 minutes. Add garlic; cook and stir 1 minute longer. Stir in squash, 1/2 teaspoon salt and 1/2 teaspoon pepper. Cook and stir until squash starts to soften, 6-8 minutes. Add 1/2 cup of water; cover and cook until squash is tender, 5-7 minutes, stirring occasionally. Stir in sage.
Step 3
Arrange bread cubes in a greased 13x9-in. baking dish. Top with bacon and squash mixture; toss gently to combine. Sprinkle with cheddar and Gorgonzola. Whisk eggs, cream, milk, Italian seasoning, remaining 1 teaspoon salt and 1/2 teaspoon pepper; slowly pour over bread mixture. Cover and refrigerate overnight.
Step 4
Remove from the refrigerator 30 minutes before baking. Preheat oven to 350°. Bake, uncovered, until a knife inserted in the center comes out clean, 50-55 minutes.
Step 5
Meanwhile, in a small skillet melt butter over medium-high heat. Stir until butter turns light brown, skim off foam. Add sage leaves, fry until just crispy, 1-2 minutes. Remove sage to paper towels to drain. Serve strata with fried sage and maple syrup.