Preheat the oven to 200 C or 400 Fahrenheit. Cut a butternut squash in half and scoop the seeds with a spoon (measuring spoons do the best work). Peel it and cut into dices. Mix together balsamic vinegar, olive oil, maple syrup, cinnamon, salt and black pepper. Combine diced butternut squash with half of the mixture. Transfer to a backing sheet lined with parchment paper.
Cut the tips off the garlic head, exposing the ends of the cloves, so that it's easier for you to peel them later. Drizzle with a bit of olive oil, sprinkle with salt and black pepper and put in butternut squash. Roast for about 30 minutes until the garlic is tender and aromatic and butternut squash is golden and tender when pierced with a fork.
Cut Brussels sprouts in halves, discarding any outer leaves that aren't firm. Toss them with the other half of the balsamic-maple mixture. Add them to the backing sheet with butternut squash and garlic 10-15 minutes before the end. Turn both butternut squash and Brussels sprouts once half-way through roasting.
While the vegetables are roasting, prepare the dressing. Mix together peeled and pitted avocado, cashew nuts, lemon juice, water, salt and black pepper with a blender or food processor. Let the garlic head cool, peel it and add to the dressing, pulsing until smooth. Adjust the consistency by adding more cashew nuts if the dressing is too liquid. Add more water if it's not liquid enough.
Combine roasted Brussels sprouts with butternut squash, pecans, cranberries and serve with the dressing on top. Sprinkle with pomegranate seeds. Enjoy!