Preheat the oven to 350 degrees F and line a baking sheet with aluminum foil.
In a small bowl, briefly stir or whisk together the maple syrup and 1 teaspoon olive oil. Place the pecans on the baking sheet, toss with the syrup mixture and spread in a single layer. Sprinkle 1/2 teaspoon salt and 1/4 teaspoon black pepper evenly on top.
Roast the pecans for 12 minutes, stirring and gently turning over every 4 minutes, until fragrant and golden. Set aside and allow to cool.
Turn the oven up to 450 degrees F and line a separate baking sheet with foil (or move the pecans to a plate while they cool, and use the same baking sheet with clean foil).
Cut off the ends of the butternut squash and use a vegetable peeler to remove the tough skin. Carefully and with a very sharp knife, slice it in half. Cut each of these pieces in half again. Remove and discard the seeds, then cut the squash into approximately 1-inch pieces.
Place the butternut squash on the prepared baking sheet and toss with 1 tablespoon olive oil. Spread in a single layer, and then sprinkle 1 teaspoon salt and 1/2 teaspoon pepper on top. Roast for 15 minutes, and then stir the squash, gently flipping pieces over so they cook evenly on both sides. Cook for an additional 10-15 minutes, until tender and lightly caramelized.
Serve the squash with maple pecans (either coarsely chopped or whole) and chopped fresh cranberries on top. You can either plate one large serving bowl with all 3 components or layer them in individual bowls.