Preheat your oven to 400°F (205°C) and line a large baking sheet with parchment paper.
In a large bowl, toss the butternut squash cubes with 2 tablespoons olive oil, ½ teaspoon kosher salt and ¼ teaspoon black pepper until evenly coated.
Spread the seasoned squash in a single layer on the prepared baking sheet, ensuring pieces aren't crowded.
Roast for 25-30 minutes, flipping halfway through, until tender and caramelized with golden-brown edges.
While the squash roasts, prepare the maple vinaigrette by whisking together maple syrup, apple cider vinegar, Dijon mustard, and garlic (if using) in a small bowl.
Slowly drizzle in the olive oil while whisking continuously until emulsified. Season with salt and pepper to taste.
If using raw pepitas, toast them in a dry skillet over medium heat for 3-5 minutes, stirring frequently until fragrant.
Allow the roasted squash to cool for about 10 minutes.
In a large serving bowl, arrange mixed greens as the base layer.
Top with the warm butternut squash, red onion (if using), and diced apple (if using).
Sprinkle with dried cranberries, toasted pepitas, and crumbled feta cheese.
Drizzle with the maple vinaigrette just before serving, starting with half the dressing and adding more as needed.
Gently toss all ingredients to distribute the dressing evenly and serve immediately.