Place the squash on a large baking sheet and drizzle with the olive oil. Toss until well coated. Season with salt and pepper. Arrange the squash in one layer and roast for 25 to 30 minutes, until the squash is tender, turning once with a spatula.
While the squash is roasting, cook the orzo according to package instructions. Drain and rinse under cold water. Drain well.
Pour the cooked orzo into a large bowl. Add the roasted butternut squash, spinach, goat cheese, pepitas, and dried cranberries.
In a small bowl or jar, whisk together the olive oil, vinegar, maple syrup (or honey), mustard, garlic, cinnamon, salt, and pepper.
Pour the dressing over the salad and toss until well combined. Season with salt and pepper, to taste. Serve immediately.