Preheat oven to 400°F (200°C). Lightly grease a foil-lined baking sheet with 1 tablespoon olive oil. Trim the ends of Brussels sprouts, remove yellow leaves, and slice each in half. In a medium bowl, toss Brussels sprouts with 2 tablespoons olive oil and salt to taste. Place cut side down on the baking sheet.

Roast in the preheated oven for 20-25 minutes. During the last 5-10 minutes, turn sprouts over for even browning. The cut sides should be nicely charred but not blackened.

On a separate foil-lined baking sheet lightly greased with 1 tablespoon olive oil, combine cubed butternut squash with 1 tablespoon olive oil, maple syrup, and cinnamon; toss to coat evenly.

Roast squash in the oven at 400°F for 20-25 minutes, turning once halfway through, until softened.

Meanwhile, preheat another oven or use the same oven set at 350°F (175°C). Line a baking sheet with parchment paper and spread pecans in a single layer. Toast for about 5 minutes, checking frequently to prevent burning. Pecans should darken in color.

In a large bowl, combine the roasted Brussels sprouts, roasted butternut squash, toasted pecans, and dried cranberries. For added sweetness, drizzle 2 tablespoons of maple syrup, toss, then taste and add up to 2 more tablespoons if desired. Mix gently to combine all ingredients evenly.