Place squash, carrots, potatoes and onions in a large bowl.
Sprinkle the rosemary, thyme, 3 tablespoons of olive oil, ¾ teaspoon salt and pepper onto the vegetables, toss to coat.
Transfer the vegetables to one of the baking sheets. Roast 35-40 minutes, stirring occasionally so they brown evenly. The amount of time will depend on your oven.
In the meantime, cut off the ends of the Brussels sprouts and pull off any yellow outer leaves. Cut large ones in half, leave small ones whole.
Place trimmed Brussels sprouts into the same bowl used for the vegetables.
Season Brussels sprouts with remaining 1 tablespoon of olive oil, ¼ tsp salt and pepper. Toss to coat.
Transfer Brussels sprouts to the second rimmed baking sheet. Bake 15 minutes until beginning to brown.
Add garlic and cranberries and toss. Continue roasting another 5-10 minutes until Brussels sprouts are brown on the outside, tender enough to pierce with a fork and cranberries begin to soften. Shake the pan from time to time to brown the sprouts evenly.
In a small bowl, mix the balsamic vinegar with honey.
When the first tray of vegetables are just about done, pour the balsamic mixture over them and toss with a spatula. Return to the oven to heat for 3-4 minutes.
Once the vegetables are tender remove them from the oven. Combine with Brussels sprouts.
Sprinkle with additional fresh herbs for additional flavor and a little salt and pepper.