Toss the delicata squash with a tablespoon of olive oil, season with salt and pepper, and bake for about 20 minutes until tender and beginning to brown.
While the squash is baking, 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.
In a large bowl, massage the kale leaves until wilted and less bitter, then transfer to a serving platter.
Top the kale with roasted squash, pomegranate seeds, wheat berries, and pepitas, and serve with the vinaigrette.