Preheat oven to 400° F. Using a sharp knife, carefully slice the acorn squash around its middle horizontally. Scoop out seeds and scrape clean. Slice into ¾ inch thick rounds. Place on a parchment paper lined rimmed baking sheet. Do not let any pieces overlap.
Using a pastry brush, brush maple syrup over both sides of squash. Bake for 10-15 minutes until the bottom side of squash is nice and golden brown. Flip and bake for another 10-15 minutes. Brush with maple syrup a second time right after removing from oven. Set aside to cool.
While Squash is baking, prepare the dressing. In a blender mix all ingredients until incorporated.
To prepare the salad for serving, Toss ½ the dressing with the arugula. Slowly add more dressing until the greens are coated with dressing but not weighed down by it. Sprinkle ¾ of the pomegranate and pumpkin seeds toss lightly. Lay roasted squash on top of the salad and sprinkle with remaining seeds.
