Heat the oven to 400°F (200°C) and cover a baking sheet with parchment paper.
Place the halved Brussels sprouts in a medium bowl. Add 2 tablespoons olive oil and 1/4 teaspoon salt, tossing until the sprouts are evenly coated.
Position the Brussels sprouts on the prepared pan with their cut surfaces facing downward. Roast for 20–25 minutes, or until the undersides are deeply browned and lightly charred without becoming blackened.
While the Brussels sprouts cook, place the cubed butternut squash in a separate bowl. Add 1 tablespoon olive oil, 2 tablespoons maple syrup, and 1/2 teaspoon cinnamon.
Toss thoroughly so the squash pieces are coated on all sides. Arrange them in one layer on a second parchment-lined baking sheet.
Roast at 400°F (200°C) for approximately 20–25 minutes, until the squash is tender. Both vegetables may be roasted simultaneously on one sufficiently large baking sheet if there is enough room to keep them well spread out.
While the vegetables roast, bring a large pot of water to a rolling boil. Add the dry pasta and cook according to the package directions, generally about 10–12 minutes, until al dente.
Drain the pasta thoroughly and set it aside. If desired for a pasta salad, briefly rinse it with a small amount of cold water to help prevent the pieces from sticking together.
Lower the oven temperature to 350°F (175°C). Arrange the pecan halves in a single layer on a baking sheet.
Toast for about 5 minutes, watching carefully, until the pecans become slightly darker and aromatic. Remove them promptly to prevent burning and allow them to cool briefly.
Transfer the cooked pasta to a large mixing bowl. Add the roasted Brussels sprouts, cinnamon-maple butternut squash, toasted pecans, and dried cranberries.
Fold the ingredients together gently until evenly distributed, taking care not to crush or break apart the tender roasted vegetables.
For a classic balsamic dressing, whisk 3 tablespoons balsamic vinegar with the optional 2 tablespoons extra-virgin olive oil. Alternatively, use balsamic glaze on its own for a sweeter, more concentrated finish.
Drizzle the chosen dressing over the pasta mixture and toss carefully until the ingredients are lightly coated.
Serve immediately while warm, or allow the pasta salad to reach room temperature before serving.