Preheat oven to 375 degrees. Wash and dry the squash. Cut lengthwise in half, clean out seeds and cut crosswise into 1/2 inch moons (the squash skin is edible). Toss with a little olive oil and then lay on a parchment lined sheet pan.
Pour cranberries onto the sheet pan and spread out around the squash. Place in oven and roast for 20 minutes, check for doneness, cook a few minutes longer if needed.
Prepare the vinaigrette: combine the maple syrup, apple juice, vinegar, Dijon and salt in a small bowl and whisk to mix well.
Thinly slice the Brussel sprouts and kale, combine in a mixing bowl with 2 tablespoons of the vinaigrette and toss well or massage to coat the greens.
When squash and berries are done cooking, toss squash, cranberries and walnuts with the shredded greens and top with more vinaigrette.