Cut squash, carrots, and cauliflower into 1 inch pieces; slice Brussels in half. Toss in 2 tablespoons olive oil, salt, and pepper, and spread onto a baking sheet. Roast for 20-25 minutes, watching so veggies do not over-cook.
Meanwhile, cook pasta as directed on package.
Once veggies are done, toss with pasta, grated Parmesan, and remaining 2 tablespoons olive oil. Serve with sliced apples on the side.