Preheat oven to 425 degrees. Spray baking sheet with cooking spray.
In large bowl, add brussels sprouts and butternut squash. Drizzle olive oil and half of the maple syrup over vegetables and mix until evenly coated.
Spread vegetables evenly on baking sheet. Season with salt and pepper and roast in the oven for 25-30 minutes. Remove from oven when edges are brown and soft in center.
Add vegetables back to large bowl. Add remaining maple syrup, pecans, and cranberries and toss together.