Toss the delicata squash with a tablespoon of olive oil and transfer it to a baking sheet. Season with salt and pepper and bake for about 20 minutes, or until tender and just beginning to brown.
While the squash is cooking, whisk together the remaining olive oil, orange juice, vinegar, maple syrup, orange zest, and cayenne pepper (if using). Season with salt and pepper to taste.
Place the kale leaves in a large bowl and massage them until they're wilted and the bitterness is gone. Transfer the kale leaves to a large serving platter. Top with the squash, pomegranate seeds, wheat berries, and pepitas. Serve with the vinaigrette.
Notes
If you've never massaged kale before, here's an article on how to do it.
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