Preheat oven to 450 degrees F.
On a large sheet pan, toss the cubed butternut squash with about 2 tablespoons olive oil, Kosher salt (about ½ teaspoon), and ground black pepper to taste. Tip: Use additional sheet pans if needed to avoid overcrowding. Overcrowding leads to steaming instead of roasting.
On another large baking sheet, toss the Brussels sprouts with about 2 tablespoons olive oil, Kosher salt (about ½ teaspoon), and ground black pepper to taste. Place the Brussels sprouts flat side down.
Roast the butternut squash and Brussels sprouts. Brussels sprouts for 15-18 minutes. Butternut squash takes 22 to 25 minutes. Tip: Try not to flip the sprouts as they roasts so the flat side can develop a golden brown color.
Remove from oven and drizzle about 2 tablespoons of maple syrup over each sheet pan and toss to coat, flipping the veggies for even browning on all sides. Return to oven and roast for an additional 5 to 8 minutes or until golden brown and tender. Note: Keep a close eye on the oven to make sure the maple syrup doesn’t burn.
Let the roasted vegetables cool down slightly for just a few minutes. Then, in a large serving bowl, toss the roasted butternut squash, roasted Brussels sprouts, dried cranberries, and pumpkin seeds together. Finish with an extra drizzle of maple syrup to taste. Enjoy!