Preheat oven to 400 F. Position rack at center. Line a small sheet pan with foil and spray or brush with oil.
In a large bowl, toss squash with 2 tablespoons of the olive oil, ¼ teaspoon each kosher salt and freshly ground black pepper, a pinch of crushed red pepper, and the rosemary. Tip the squash mixture out onto the prepared sheet pan and spread evenly. Roast about 30 minutes or until tender, turning once midway through roasting time. Remove to rack to cool.
Meanwhile, add the other tablespoon of olive oil to a medium skillet, heat over medium high flame, and tilt the skillet to spread the oil. Add the sliced mushrooms; sprinkle lightly with black pepper. Sauté, for 5-7 minutes until tender, stirring several times, and adding the sliced garlic for the last two minutes. Sprinkle with a little kosher salt and remove from heat.
Add the baby arugula to a large serving bowl or platter and sprinkle lightly with salt, pepper and crushed red pepper; toss. Place the roasted squash pieces evenly over the greens and spoon the mushrooms on top. Scatter the olives within the salad (make sure they can be seen) and drizzle with the blue cheese dressing. Grind some black pepper over the entire salad. Serve at room temperature or cover loosely and store undressed in refrigerator for no more than two hours, drizzling with dressing and grinding pepper over just before serving. This salad is edible the following day--don't pitch it-- but is really best the day it’s made.MAKE AHEAD: You can cook the squash and mushrooms a day ahead, cover well and refrigerate overnight. Bring to room temperature before making the salad. The blue cheese dressing can also be made a day ahead and stored in a tightly covered jar in the refrigerator.