Preheat oven to 400 degrees F. Cut both squash in half along the ribs, lengthwise. Scoop out seeds and stringy pulp; discard.
Brush cut sides of squash halves with the olive oil; season with salt and pepper. Place, cut sides down, on a rimmed baking sheet coated with cooking spray.
Transfer to the oven and cook until tender when pierced with the tip of a paring knife, about 40 minutes.
Meanwhile, in a medium pot, cook rice according to package directions.
Remove rice from heat, and stir in dried cranberries and pecans; season with salt and pepper.
Dividing mixture evenly among the squash and serve!