Preheat oven to 400 F. Toss butternut squash with 2 tsp oil and 1/4 tsp salt. On baking sheet, spread out and roast butternut squash until darkened and tender, stirring once, about 30 minutes.
Into high-speed blender container, place dates, maple syrup, cider vinegar, 2 Tbsp oil, thyme, mustard, garlic, and 1/4 tsp salt. Blend until smooth. If dressing is too thick, thin with a small amount of water.
Divide kale, butternut squash, apple slices, and pecans among serving plates. Drizzle on date dressing and scatter on granola.
Per serving: 450 calories; 10 g protein; 17 g total fat (2 g sat. fat); 75 g total carbohydrates (32 g sugars, 14 g fiber); 388 mg sodium