Step 1: Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper for easy cleanup.
Step 2: Brush the flesh of the halved acorn squash with 1 tablespoon of olive oil and the maple syrup. Season with salt and pepper. Place them cut-side down on the baking sheet and roast for 30-35 minutes until tender.
Step 3: While the squash roasts, rinse the wild rice and combine it with the vegetable broth in a medium saucepan. Bring to a boil, then reduce heat to low, cover, and simmer for 40-45 minutes or until tender.
Step 4: In a skillet, heat the remaining tablespoon of olive oil over medium heat. Sauté the onion and celery for 5-7 minutes until soft. Stir in the garlic, thyme, and rosemary for another minute.
Step 5: Once the rice is cooked, fluff it with a fork and stir it into the skillet with the sautéed vegetables. Fold in the dried cranberries and pecans. Season the pilaf with salt and pepper.
Step 6: Flip the roasted acorn squash halves over so they are cut-side up. Generously spoon the wild rice pilaf into the centers of each squash.
Step 7: Return the stuffed squash to the oven for another 10-15 minutes to allow the flavors to meld and the tops to slightly brown. Serve warm.