Preheat oven to 425 degrees.
Cut butternut squash into chunks and toss with 3 tablespoons olive oil, salt and pepper. Spread on a parchment lined baking sheet and roast for about 30 minutes until soft and lightly browned.
Toss cauliflower with 3 tablespoons olive oil, salt, and pepper and place on a parchment lined baking sheet and roast for about 25 minutes until soft and lightly browned.
In a medium pot combine water, 2 tablespons olive oil, and salt and bring to a boil. When water is boiling, add couscous, stir vigorously and continue cooking for about 5 minutes. Do not overcook. Remove from heat, cover and let rest for about 5 minutes. Uncover and fluff with a fork before serving.
Meanwhile, combine roasted veggies and wilted kale in a large bowl.
When couscous is cool toss cranberries and pumpkin seeds into the veggie mixture. Stir in couscous. Sprinkle with feta or blue cheese and add about half the dressing to the coat the salad.