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- 8 tablespoons extra-virgin olive oil
- 3 tablespoons balsamic vinegar
- 1/2 medium shallot, minced
- Kosher salt and freshly ground black pepper
- 1 1/2 cups 1/2-inch cubed butternut squash
- 1 bunch kale, stems removed, cut into 1/2-inch wide ribbons (about 5 cups)
- 3/4 cup whole almonds, toasted, coarsely chopped
Preheat oven to 425°. Line a baking sheet with foil. Whisk 5 Tbsp. oil, vinegar, shallot, and Dijon mustard in a small bowl. Season to taste with salt and pepper. Set aside. Combine squash and 2 Tbsp. oil in a medium bowl and toss to combine; season with salt and pepper. Transfer squash to prepared baking sheet and roast, turning occasionally, until squash is tender and lightly golden, about 20 minutes. Let cool slightly.
Meanwhile, heat remaining 1 Tbsp. oil in a large skillet over high heat. Add kale and cook, tossing frequently, until bright green and slightly wilted, 1–2 minutes. Remove from heat; add 3–4 Tbsp. dressing and toss to coat. Transfer kale to a baking sheet and cool slightly, about 5 minutes.
Add reserved squash and almonds to kale; toss well and season with pepper. Divide among bowls; drizzle with more dressing, if desired. Using a vegetable peeler, shave Parmesan over.