For cookie base, combine 1 cup cookie crumbs and 1 tbsp milk, mixing with fork until blended. Press 2 tbsp crumb mixture into bottom of 3 glasses; reserve remaining crumb mixture. Place glasses in freezer.

Combine cinnamon and 1/2 cup of the reserved cookie crumbs. Place remaining milk, ice cream, cinnamon crumb mixture and semisweet Chocolate chips in blender. Blend until smooth.

Pour chocolate mixture over cookie base in prepared glasses. Garnish with whipped cream, remaining crumb mixture or miniature creme filled cookies.