Preheat the oven to 400 degrees F.
In a bowl, toss all the vegetables, except the tomatoes, with 1 1/2 tablespoons oil. Season with salt and pepper, to taste. Arrange on a baking sheet and roast, until caramelized, about 30 minutes, turning vegetables halfway through the cooking time. In a small bowl, add the tomatoes and the remaining olive oil and toss to coat. Season with salt and pepper, to taste, and add to the baking sheet, at the halfway point of cooking, to caramelize.
Meanwhile, in a large skillet over medium heat, add the sausage and saute until cooked through. Turn up the heat and deglaze with white wine. Once the vegetables are cooked, cool slightly, then coarsely chop. Add the vegetables and any pan juices to the sausage in the skillet. Toss in the cooked penne, adding reserved pasta water, if needed, to moisten. Season with salt and pepper, to taste, and serve in bowls topped with Parmesan.