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Preheat oven to 400 degrees F. Line baking sheet with parchment paper.
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In bowl, toss butternut squash cubes with olive oil, salt, pepper, sage and cinnamon.
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On prepared baking sheet, spread out squash in single layer. Roast 25 minutes, tossing halfway through, until tender and caramelized.
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Place chopped kale in large bowl. Drizzle with 1 tablespoon olive oil and small pinch of salt. Massage with hands for 1-2 minutes until softened.
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In bowl, whisk together apple cider vinegar, maple syrup, Dijon mustard, sour cream, olive oil, salt and pepper until smooth.
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To bowl with kale, add roasted squash, apple, cranberries and pumpkin seeds. Drizzle with dressing and toss to combine.