Preheat your oven to 400°F (200°C). Lightly drizzle or spritz a baking sheet with extra virgin olive oil. Place the diced butternut squash onto the prepared sheet and drizzle with additional olive oil. Sprinkle the squash with your preferred amount of salt, black pepper, and garlic powder. Toss everything gently so the squash is evenly coated in oil and seasonings.
Spread the seasoned squash evenly on the baking sheet and roast on the center rack of your oven for 25 minutes. This initial roasting time helps the squash become tender and slightly golden.
After the squash has roasted for 25 minutes, carefully pull the oven rack out and scatter the fresh cranberries over the partially roasted squash. Return the baking sheet to the oven and roast for an additional 10 to 15 minutes, or until the cranberries are soft and begin to burst. I like seeing the cranberries get a little jammy, as it brings a nice tartness to the dish.
Remove the tray from the oven. While the squash and cranberries are still hot, sprinkle ground cinnamon over the top (start with about 1/8 teaspoon and adjust to your taste). Drizzle with honey and sprinkle with finely crumbled feta. Toss everything gently to combine. If you like things a bit sweeter, you can always add more honey to taste.
Transfer the roasted squash and cranberry mixture to a serving dish. Garnish with chopped fresh parsley or a sprinkle of dried parsley for a vibrant finish. Serve while hot and enjoy! I find that the freshness of the parsley adds a nice pop of color and a subtle herbal note right at the end.