Toss the squash in the olive oil and season with salt and pepper. Spread out on a parchment paper or foil lined baking sheet. Make sure the pans are not overcrowded. Bake squash about 20 – 25 minutes or until slightly tender and golden brown, turning over half way through. Set aside to cool.
Place salad greens in a large bowl with squash, pecans and cranberries. Toss with enough salad dressing to lightly coat the salad greens, then divide into serving bowls. Top with blue cheese crumbles and pear slices and serve right away.