This luscious dessert requires several steps, but most of the work can be done well in advance of serving, making it an easy and stunning finale to a dinner party.
In a small mixing bowl, mix together dried cranberries, orange zest, hazelnuts, and 2 tablespoons brown sugar; set aside.
Preheat oven to 400°. Butter a 9x9-inch glass or enamel baking dish; set aside. Peel pears. Slice ¼ inch off the bottom of each pear, creating a flat bottom. Working from the bottom of each pear, use a melon baller to scoop out the center, creating a hollow about 1 inch wide. Leave the top intact. Stand each pear in a greased baking dish and brush with some butter; sprinkle the remaining brown sugar over pears. Cover tightly with aluminum foil; bake 50 to 60 minutes, or until pears are easily pierced with a paring knife. Keep covered and cool completely. Transfer to a plate. Strain the juices from the baking pan into a bowl and reserve for the sauce.
Reduce oven heat to 350°. Carefully press the cranberry filling firmly into each pear hollow.
Unroll phyllo sheets onto a flat, dry surface; cover immediately with plastic wrap and then a damp towel (phyllo can dry out quickly). Carefully remove one sheet of phyllo; lay on a dry, flat surface. Lightly butter the surface of the dough and sprinkle with sugar. Layer with another sheet; cut in half widthwise. Place a cookie in the center of each half (this helps keep the pear from breaking through the delicate phyllo); place a pear on each cookie. Mold dough around a pear from the bottom up, forming a pleated pouch. Pinch (do not twist) dough firmly against the top of the pear at the stem, arranging the excess to create a dramatic top. Transfer to a baking sheet. Repeat process with the next 5 pears. Bake 10 to 15 minutes, or until the tops are browned and the sides are firm; transfer to a serving platter. While the pears are baking, add cider to the reserved baking liquid. Simmer 8 to 10 minutes over medium heat until sauce thickens; serve with the pears.