Peel butternut squash. Cut in half and scoop out the seeds. Cut it into small cubes. Toss it in olive oil and spread out on a baking sheet. Salt and pepper the squash before roasting.
To prepare the brussels sprouts, remove any yellow or brown outer leaves, cut off the stems and cut in half.
In a large bowl, toss the brussels sprouts, olive oil, salt and pepper together. Once all of the brussels sprouts are coated in oil, spread them into a 9-by-13-inch (or larger) baking dish or sheet tray to roast. Note: You may want to line your sheet tray with parchment for easy cleanup.
Roast the squash and the brussels sprouts. Check them after 15 minutes, maybe shaking the tray or turning the tray (especially if your oven doesn't cook evenly - mine tends to get hotter at the back of the oven).
Continue to roast the butternut squash until they are fork tender (about 45 minutes total roasting time) and the brussels sprouts til they are crispy on the outside.
On another tray spread out the pecans for roasting. Add these for the last 5 minutes of baking time.
Toss together the squash, brussels sprouts, pecans, and cranberries and drizzle with maple syrup for serving.