Preheat the oven to 400°. On a rimmed baking sheet, toss the squash with 2 tablespoons of the olive oil and season with salt and pepper. Roast the squash for 20 to 25 minutes, until tender. Transfer to a large bowl.
Meanwhile, in a medium saucepan, cover the wheat berries with 5 cups of water and 1/4 teaspoon of salt and bring to a boil. Simmer over moderate heat until tender, 25 minutes.
Add the kale to the wheat berries, cover and remove from the heat; let stand until the kale is wilted, 5 minutes. Drain well and add the wheat and kale to the squash. Add the vinegar and 2 tablespoons of the oil to the salad, season with salt and pepper and toss.
In a medium skillet, heat the remaining 2 tablespoons of oil. Add the shallots and a pinch of salt and cook over moderately high heat until just starting to brown, 3 to 4 minutes. Add the sage and cook for 1 minute, until fragrant. Add the garlic and cook, stirring, for 1 minute. Add the wine and simmer, stirring, until evaporated. Scrape the shallot and garlic into the salad and toss. Season with salt and pepper, garnish with parsley and serve.