Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper. Drizzle the squash halves with 1 tablespoon of olive oil and season with salt and pepper. Place them cut side down on the baking sheet and roast for about 40–45 minutes, until fork-tender and lightly caramelized.
While the squash roasts, rinse the wild rice under cold water. In a medium saucepan, combine rice, vegetable broth, thyme, sage, and garlic powder. Bring to a boil, then reduce to a simmer, cover, and cook for about 35–40 minutes or until the rice is tender and the liquid is absorbed. Remove from heat and fluff with a fork.
Transfer the cooked rice to a large bowl. Stir in cranberries, chopped pecans, parsley, lemon juice, and the remaining 1 tablespoon of olive oil. Taste and adjust with more salt or lemon as needed. If you’re adding cheese, stir it in now for a creamy touch.
Once the squash is cool enough to handle, flip it over and gently scoop out a small amount of flesh from each half to make room for the filling. Don’t dig too deep—just enough for a nice pocket. Mix the scooped-out squash into your wild rice mixture.
Spoon the wild rice filling into the squash halves, mounding slightly. Return them to the oven and bake uncovered for another 10–15 minutes, just to warm everything through and lightly crisp the top.
Top with a sprinkle of parsley or extra nuts for crunch. Serve warm as a main dish or hearty side. Leftovers reheat beautifully too!