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Step 1
Position racks in the middle and lower third of the oven and preheat to 400 degrees. Place the squash on a large, rimmed baking sheet, drizzle with 2 teaspoons of the oil, 2 teaspoons of the maple syrup and 1/8 teaspoon of the salt, and toss to coat. Arrange the squash pieces in a single layer and roast (middle rack), stirring once, for 15 to 20 minutes, or until tender and browned. Transfer the baking sheet to a wire rack and let the squash cool.
Step 2
While the squash is roasting, spread the pumpkin seeds out on a small, rimmed baking sheet and toast in the oven (lower rack) for about 5 minutes, or until fragrant. Set aside to cool.
Step 3
In a small bowl, whisk together the remaining 3 tablespoons of olive oil, the vinegar, onion or shallot, the remaining 1 tablespoon of maple syrup, the mustard, the remaining 1/4 teaspoon of salt and the pepper.
Step 4
In a large bowl, toss the kale with the dressing, massaging it gently with your hands to soften it a bit. Divide the kale among 4 serving plates, then top each with the roasted squash, and pumpkin and pomegranate seeds.