Saw this on the Weber Grill site and decided to try it. Some prep work involved but very good. Pretty filling by itself but we served this with cheese ravioli on the side. This stuffed squash would also be great with pork or turkey.
Grill squash halves, cut side down, over indirect medium heat for 40 minutes, turning once about half way through. Remove from the grill and let stand at room temperature.
Meanwhile, in a small saucepan over medium heat, cook cranberry juice until reduced to about 1/3 to 1/4 cup, this should take about 20 minutes.
Grill the apple, cut side down, over direct medium heat, for 8 to 10 minutes, turning once. Allow apple to cool slightly; chop and set aside. In a large pan over medium heat, warm the olive oil. Add the garlic and onion and sauté until the onion is translucent, about 4 minutes. Turn heat off and add the chopped apple, crumbled cornbread, crandberries, pecans, tyme and sage. Add salt and pepper to taste. Mix to combine ingredients.
Spoon about 1 tablespoon of the reduced cranberry juice in the cavity of each squash half and then spoon in about 1/2 cup of the stuffing. Grill stuffed squash over medium heat until the squash is tender and the stuffing is golden, about 5 - 8 minutes.