Preheat oven to 400°F (200°C) and line a large baking sheet with parchment paper.
Toss cubed sweet potatoes and butternut squash with 2 tablespoons olive oil, salt, and pepper on the baking sheet.
Roast vegetables for 25-30 minutes, or until tender and lightly browned.
While vegetables roast, bring a large pot of salted water to a boil. Cook orzo according to package directions until al dente, approximately 8-10 minutes.
Drain the orzo and rinse briefly with cool water to stop the cooking process; transfer to a large mixing bowl.
In a small jar or bowl, whisk together the apple cider vinegar, maple syrup, Dijon mustard, and 1/3 cup extra virgin olive oil to create the vinaigrette.
Add the roasted vegetables, chopped baby kale, dried cranberries, and toasted pecans to the bowl with the orzo.
Pour the vinaigrette over the salad and toss until ingredients are evenly coated.
Gently fold in the crumbled feta cheese and serve warm or at room temperature.