Preheat oven to 425℉. Line a baking sheet with parchment paper.
Place the Brussels sprouts and squash on the baking sheet. Drizzle about a tablespoon of olive oil, and sprinkle with salt and pepper. Toss to combine. Roast until tender, about 20-25 minutes, tossing halfway through the cooking time.
While the veggies roast, cook the bacon pieces in a skillet over medium heat until crispy. While the bacon is cooking, whisk together the pomegranate juice, cider vinegar, Djion, and maple syrup.
Once the bacon is cooked, use a slotted spoon to transfer the pieces to a paper towel-lined dish.
Measure out 3 tablespoons of the bacon fat to keep in the hot skillet (or remove all of the bacon fat and replace with 3 tablespoons of olive oil). Whisk in the pomegranate juice mixture and stir over low heat until heated through. Stir in the pomegranate seeds and bacon pieces. Keep warm until the veggies are done roasting.
Remove the veggies from the oven and place in a serving bowl. Drizzle the warm pomegranate dressing on top and toss to combine. Serve and enjoy!