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Preheat oven to 400 degrees.
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Toss butternut squash in olive oil, salt and pepper. Roast in preheated oven for 20-25 minutes.
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Throw bacon in a medium skillet and cook until about halfway done. Add Brussels sprouts and cook over medium heat for 10-15 minutes. Stirring occasionally.
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The Brussels sprouts should have char spots on them and be tender. (For larger Brussels sprouts, you may have to cook longer).
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Toss squash and sprouts together. Add salt and pepper to taste.
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Serve immediately topped individually with a drizzle of balsamic vinegar.