Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper or leave unlined.

In a large bowl or directly on the baking sheet, toss the cubed butternut squash and diced apple with 2 tablespoons of extra virgin olive oil, sea salt, and black pepper. Spread into a single layer and roast for 25–30 minutes, tossing halfway through, until squash is fork-tender and caramelized around the edges.

While squash roasts, bring a large pot of salted water to a boil. Add the dry orzo pasta and cook for 8–10 minutes until al dente. Drain thoroughly in a fine-mesh colander and toss with a light drizzle of olive oil to prevent clumping.

In a small bowl or jar, whisk together 3 tablespoons extra virgin olive oil, apple cider vinegar, pure maple syrup, Dijon mustard, and minced garlic until fully emulsified.

In a large serving bowl, combine warm cooked orzo, roasted butternut squash and apples, and dried cranberries. Drizzle maple cider dressing over top and toss gently.

Fold in toasted pecans and crumbled Greek feta cheese gently right before serving so cheese stays intact. Garnish with chopped fresh thyme or parsley. Serve warm or at room temperature.