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Preheat oven to 425°F. Line a large rimmed baking sheet with parchment paper.
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Spread squash and onion on the prepared baking sheet. Drizzle with oil and maple syrup; sprinkle with kosher salt. Stir to coat and spread in an even layer. Roast until tender, about 20 minutes.
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Meanwhile, combine kale and lemon juice in a large bowl; toss to coat. Let stand while the squash is baking, allowing the kale to soften.
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Add the roasted vegetables to the kale; toss to combine. Top with goat cheese, pepitas, flaky salt and cracked pepper.