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.
Each pear lengthwise in half. 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.
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:
1/4 cup (50 mL) pudding into bottom of parfait glass; sprinkle with 1 Tbsp. (15 mL) crushed cookies. Cover with layers of 1/4 cup (50 mL) each diced pears and pudding. Garnish with 1 Tbsp. (15 mL) whipped topping and 1/4 tsp. (1 mL) crushed cookies. Top with 1 fanned-out pear piece.