Heat oven to 350° F. In medium bowl, mix peanuts, sugar, butter and 1/2 teaspoon cinnamon. Remove 1/4 cup and spread on small baking sheet. Divide remaining peanut mixture among four (4-inch) tart pans with removable bottoms. Press firmly onto bottom and sides of each pan.
Bake tart crusts and peanut mixture together 8 minutes. Cool on wire racks.
In medium microwavable bowl, microwave chocolate milk on high 45 seconds. Add chocolate; stir until completely melted and smooth. Set aside.
In large bowl, using electric mixer on medium speed, beat peanut butter, sweetened condensed milk, vanilla and remaining cinnamon until smooth. Add heavy cream; beat until soft peaks form. Spread in prepared tart crusts. Spread chocolate mixture over top.
Refrigerate at least 1 hour, or until ready to serve. Cut each tart in half. Sprinkle with toasted peanut crumble.