For the Basting Sauce: Combine apple cider, dessert wine, and brown sugar in a bowl until sugar is dissolved. Set aside. Can be made up to 1-2 hours ahead of time.
For the Dressing: Combine olive oil, lemon juice, and 1/2 cup of the basting sauce. Set aside at room temp.
Peel and slice pears in half lengthwise. Carefully remove core and seeds from pears, leaving a rounded well for filling later. Trim away a tiny slice from bottom of each pear so they sit flat on roasting pan. Spoon some basting sauce over each pear, and bake until tender (approx. 30 min). Baste pears with sauce a couple more times while baking.
Prepare individual plates by dividing the baby greens mixed with arugula. When pears are partly cool, place on top of the greens. Fill each pear with a mixture of crumbled Gorgonzola, dried cranberries, and pecans. Sprinkle remaining mixture over rest of the salad. Generously drizzle lemon dressing on top of pears and greens. Sprinkle with cracked pepper and enjoy!