Place water and rice in a medium saucepan and bring to a boil. Cover, reduce heat to a low simmer, and cook for 40-45 minutes until water is absorbed. Remove from heat and let stand for 10 minutes with the lid still on. Fluff with a fork.
Meanwhile, preheat oven to 425 degrees F. Place butternut squash on a rimmed baking sheet and toss with the 1 ½ tablespoons of olive oil. Roast in the preheated oven for 35-40 minutes, turning once halfway through, until tender.
Toast the pecans by placing them in a small skillet over medium heat until fragrant. Watch them closely as they can go from toasted to burnt quickly.
In a large bowl, combine the cooked rice, roasted squash, toasted pecans, apple pieces, dried cranberries, and shallot.
In a small bowl, whisk together all dressing ingredients. Pour dressing over the salad and toss gently to combine. Salad can be served warm, at room temperature, or chilled.