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Position rack in middle of oven. Preheat oven to 425°F/220°C.
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Place squash cubes on rimmed half-sheet baking pan. Drizzle with about 1 tablespoon of the garlic-infused oil and season with salt and pepper. Toss to coat evenly.
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Roast for about 20 minutes, then stir squash around and continue roasting until lightly browned and fork tender, about 20 to 30 minutes more. Set aside. Squash may be roasted the day before serving. Simply refrigerate in an airtight container and bring to room temperature before proceeding.
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Meanwhile, heat 1 teaspoon garlic-infused oil in a small skillet (we like nonstick) over medium heat. Add pepitas and cook stirring frequently until they are just beginning to color, about 2 minutes. Scrape out onto a paper towel to absorb excess oil; set aside. Pepitas may be toasted the day before serving, too. Simply store at room temperature in an airtight container.
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Make dressing by whisking together remaining garlic-infused oil, lemon juice, Dijon mustard and maple syrup. Season to taste with salt and pepper.
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At least 1 hour before serving, place kale in a large mixing bowl and slowly add dressing, tossing to coat well. (You might not need it all). Let sit for 1 hour, during which you should toss the kale a few times to keep it evenly coated in the dressing. Right before serving add the roasted squash, pepitas, Parmesan and pomegranate seeds, tossing to mix evenly. Taste and season with additional salt and pepper if desired. Salad is ready to serve. Leftovers can be refrigerated for up to 2 days but the quality will diminish somewhat and definitely make sure to bring the salad to room temperature before serving.