Prepare couscous according to package directions.
Heat olive oil in large sauce pan over med-high heat. Dice squash and set aside. Dice shallot, sauté for 1 minute. Add squash, add to pan along with cranberries, cherries, and 1 1/2 cups apple juice. Cook for 15 minutes, until squash is softened. The juice will be almost gone. Add cinnamon.
Place this mixture into the couscous.
In a small bowl, whisk together remaining apple juice, canola oil, vinegar, salt and pepper (to taste). Pour over couscous mixture, toss, add nuts and pineapple, serve warm or at room temperature. (we served ours separately, kids preference, but super delicious together!)