Preheat oven to 400 degrees F. Cut the acorn squash into ½ inch slices (no need to peel the skin, but do remove the seeds). Arrange on a sheet pan, and drizzle with some olive oil and sprinkle with some salt and pepper. Roast for about 20-25 minutes, or until softened, flipping halfway through. Once ready, remove from the oven and let it cool slightly.
Meanwhile, make the apple cider vinaigrette: Add all the vinaigrette ingredients in a mason jar. Shake well until combined. You can adjust the ingredient quantities to taste too. Set aside.
In a large bowl, toss the sliced kale and Brussels sprouts with some of the prepared vinaigrette. This will help soften the kale and Brussels sprouts.
Arrange the salad: on a platter, arrange the prepared kale and brussels sprouts along with the sliced apples, roasted acorn squash, cheese, pecans, and pumpkin seeds. Drizzle with the remaining apple cider vinaigrette. Serve immediately. Enjoy!