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.
The salad can be refrigerated overnight. Bring to room temperature before serving.