POACHED Pears: Simmer first 4 ingredients in saucepan small enough to cover pears in liquid. Add pears; poach 45 min. or until tender, stirring occasionally. Cool quickly to avoid overcooking.
CUT each pear lengthwise in half. Cut off curved piece from side of each pear half; cut into thin slices and fan out. Set aside. Discard pear cores and stems; dice remaining pears.
PUDDING: POUR milk into mixer bowl fitted with whip attachment. Add pudding; beat on low speed 15 sec. Scrape bowl; beat on medium speed 2 min. Let stand or refrigerate at least 15 min.
FOR each serving: Spoon 1/4 cup pudding into bottom of parfait glass; sprinkle with 1 Tbsp. crushed cookies. Cover with layers of 1/4 cup each diced pears and pudding. Garnish with 1 Tbsp. whipped topping and 1/4 tsp. crushed cookies. Top with 1 fanned-out pear piece.