Preheat the oven to 375ºF. Remove the stems from the acorn squash and cut the dried part off the bottom. Scrape the seeds out with a spoon and discard. Using a basting brush, lightly coat the fleshy part of the squash with olive oil. Season with salt and fresh cracked pepper to taste. Bake in a 375ºF oven for 45 minutes to an hour, or until the flesh is soft and creamy.
Meanwhile, cook your wild rice by combining with water, 1/4 tsp salt and 1 tsp of olive oil in a saucepan. Bring to a boil, reduce to a simmer, and cook on medium-low heat for 45 minutes to an hour.
About 15 minutes before the squash and the rice are going to finish cooking, make your stuffing. Sauté the diced celery and onion in a skillet with 1/2 Tbsp of olive oil until soft. Add the spices to the pan and cook for an additional minute, then remove from the heat. Fold in the cooked wild rice, cranberries, and pecans.
Scoop the rice stuffing into the cooked acorn squash bowls so that they are heaping full. Cover and return to the oven for 5 to 10 minutes or until heated through. Serve immediately.