Cut the top off the squash and then slice it in half lengthwise. Cut each half in 1/2 inch half rounds. Place them in a medium bowl. Add the pear halves and toss them with 1 tbsp extra virgin olive oil.
Place the squash and the pears on a lined sheet pan and place it in the middle of the preheated oven. Roast for 15 - 20 minutes, flipping the squash and pears part way through once they are browned on one side.
Place the greens on a medium platter. Top with the roasted squash, pears, cranberries and pumpkin seeds. Drizzle with the dressing.
Make the Salad Dressing
Place olive oil in a bowl or glass jar with a tight-fitting lid.
Gradually whisk in the balsamic vinegar, pear juice, and salt and pepper. (or add them to the jar and cover tightly and shake well.