Cook's Note: For the best results, chill the blender jar and glasses in the freezer for 1 hour before making.
Place the milk chocolate bar in a microwave-safe bowl. Using the defrost setting, microwave for 1 to 2 minutes, stirring every 30 seconds, until melted. Allow to cool.
Blend the ice cream, milk, melted chocolate, almond extract, and cinnamon in a blender jar (preferably chilled) until the mixture is combined. Add the frozen candy covered chocolate and pulse several times to chop them into small bits and blend them into the ice cream mixture. Serve in chilled juice-size glasses with spoons.