Preheat oven to 400℉. Place brussels sprouts and squash in a large bowl and toss with coconut and olive oil, 1/4 teaspoon salt and a pinch of pepper.
Transfer to 2 parchment paper-lined baking sheets. Roast for 25 - 30 minutes until crisp tender and lightly browned.
Place cranberries, pecans, and shallots in a bowl and toss with remaining 1 tablespoon olive oil. Transfer to a lined balking sheet and place in oven with sprouts and squash for the last 10 minutes of roasting time.
Meanwhile, whisk together remaining ingredients in a small bowl.
When vegetables are finished roasting toss all together with the maple mustard dressing in a large bowl. Transfer to a serving platter to serve.