Preheat oven to 400°F (200°C) and line a rimmed baking sheet with parchment paper. Toss cubed butternut squash with 1 tablespoon olive oil, cinnamon, salt, and pepper, then spread in a single layer.
Roast for 25 to 30 minutes, stirring once halfway through, until fork tender and lightly caramelized at the edges. Set aside to cool slightly.
Bring a large pot of generously salted water to a boil. Cook orzo according to package instructions, usually 8 to 9 minutes, until al dente.
Drain orzo in a colander and rinse briefly under cold water to stop the cooking process. Shake off excess water and set aside to drain fully.
Add chopped pecans to a dry skillet over medium heat. Toast for 3 to 4 minutes, stirring frequently, until fragrant and slightly darkened.
Transfer pecans to a plate to cool immediately to prevent burning.
In a small bowl or jar, combine balsamic vinegar, maple syrup, Dijon mustard, and minced garlic. Whisk until fully incorporated.
While whisking continuously, slowly drizzle in the remaining tablespoon of olive oil to emulsify. Season with salt and pepper, then taste and adjust sweetness or acidity.
Add cooled orzo to a large mixing bowl. Add chopped baby kale or spinach and toss to combine, allowing residual warmth to slightly soften the greens.
Gently fold in roasted butternut squash, dried cranberries, toasted pecans, and thinly sliced red onion until evenly distributed.
Pour about three quarters of the maple balsamic vinaigrette over the salad and toss gently to coat. Taste and add remaining vinaigrette if desired.
Sprinkle crumbled feta cheese over the top just before serving, folding it in very gently to keep crumbles intact.
Serve immediately at room temperature, or chill for at least 30 minutes for a cold version.