Mix peanuts, sugar and butter in medium bowl. Remove 1/4 cup and spread on small baking sheet. Divide remaining peanut mixture among 4 (4-inch) tart pans with removable bottoms. Press firmly onto bottom and up sides of each tart pan.
Bake tart crusts and peanut mixture together in preheated 350°F oven 8 minutes. Cool on wire racks.
Meanwhile, microwave chocolate milk in medium microwavable bowl on HIGH 45 seconds. Add chocolate; stir until chocolate is completely melted and mixture is smooth. Set aside.
Beat peanut butter, sweetened condensed milk, vanilla and cinnamon in large bowl with electric mixture on medium speed until smooth. Add heavy cream; beat until soft peaks form. Spread in prepared tarts crusts. Spread chocolate mixture over top.
Refrigerate 1 hour or until chilled. Sprinkle with toasted peanut crumble before serving.
To crush peanuts: Place peanuts in large resealable plastic bag. Pound with a rolling pin, mallet or heavy skillet until lightly crushed.