Cook the wheat berries according to the directions in this recipe.
Preheat the oven to 400°F and line a large baking sheet with parchment paper. Roast the butternut squash for 30 to 35 minutes. Add the shallots onto the baking sheet with the squash and roast for 20 to 25 minutes. Wrap the sage leaves in foil with a drizzle of olive oil and place on the baking sheet for the last 2 minutes. Unwrap and chop.
Prepare the Apple Cider Vinegar Dressing according to this recipe.
In a large bowl, massage the kale with a bit of the dressing. Add the wheat berries, squash, shallots, sage, walnuts, cranberries, parsley, thyme, ½ teaspoon salt, lots of pepper, and toss. Transfer to a platter, drizzle with more dressing and more freshly ground black pepper. Top with the pecorino cheese and serve.
*Note: if you don't love sage, you could use less. We adore it and we love how it enhances the fall flavors in the salad.