Preheat convection oven to 350°.
Cut each squash in half and remove seeds. Melt butter with maple syrup in a small sauce pan. Place squash halves on a parchment-lined sheet pan and brush with butter and maple mixture. Season with salt and pepper. Bake in oven until squash is very soft and edges are browning. A knife will easily pierce the flesh. Remove squash from oven, brush again with butter and maple mixture and cool.
Toast pecans on an unlined half sheet pan for 4¬5 minutes.
Steam the rice with water until all the water is absorbed and rice grains are cooked through with some tooth left. Put cranberries on top and cool.
Whisk together olive oil and cider vinegar and pour over rice and cranberries. Drizzle over the remaining maple syrup. Add celery, scallion rings, and pecans. Mix it all together.
Using an appropriate-sized scoop for the size of the squash, usually 3¼-ounces , fill the squash cavities with rice mixture. Arrange on a platter.