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Preheat oven to 425°F. Place the halved butternut squash on a baking sheet, drizzle with olive oil, and season with salt and pepper.
Top with fresh rosemary and thyme. Roast for 35-40 minutes, or until fork-tender.
Let cool for 10 minutes, then cube into bite-sized pieces.
In a skillet over low-medium heat, add olive oil and toast the walnuts for 4-5 minutes until fragrant.
Set aside and let cool for 5 minutes.
In a blender or food processor, combine toasted walnuts, olive oil, Dijon mustard, honey, red wine vinegar, and garlic cloves.
Blend until smooth. Season with salt and pepper. If dressing is too thick, add 1 tsp of water until the desired consistency.
In a large bowl, combine kale, shaved Brussels sprouts, sliced apples, Parmesan, and dried cranberries.
Add the roasted and cubed butternut squash.
Drizzle with toasted walnut vinaigrette and toss until well coated.
Finish with freshly grated Parmesan, an extra sprinkle of salt and pepper, and serve immediately.