Preheat the oven to 400°. Toss squash with 2 tbsps of olive oil and season with salt and pepper. Roast the squash on a baking sheet for 25 minutes or until tender.
Heat a pot with 5 cups of water, salt, and wheat berries. Bring to a boil and immediately reduce to a simmer for 25 minutes until tender.
Add the kale to the pot and remove from heat. Cover the pot and let stand for 5 minutes. Drain the remaining water and transfer the squash and wheat berries to a large bowl.
Add the sherry and season with salt and pepper.
In a skillet, heat the remaining 2 tablespoons of oil. Add the shallots and cook until they begin to change color. Stir in the sage, garlic, and cranberries and cook for 2 minutes. Add the wine and cook until the wine evaporates. Scrape the shallot and garlic into the salad and toss. Top with the chopped parsley and serve.