Preheat oven to 425°F. Line a rimmed baking sheet with parchment.
Toss squash with roasting oil, maple syrup, smoked paprika, 3/4 tsp salt, and 1/4 tsp pepper.
Spread on the sheet and roast 25–30 minutes, flipping halfway, until browned and tender. Cool 5 minutes.
Whisk dressing oil, cider vinegar, Dijon, and dressing maple with remaining salt and pepper.
Add greens, red onion, pecans, and cranberries to a large bowl.
Add warm squash to the bowl.
Drizzle with dressing and toss gently to coat. Top with feta and serve.