To a blender, add 1/2 cup of milk, 1/2 cup of coffee, 1/4 cup of syrup, and the cinnamon. Puree to combine ingredients. Add 1 pint ice cream and blend until smooth. Pour into 2 frosted fountain glasses or tall glasses and garnish with swirls of whipped cream, an extra pinch of cinnamon, and some chocolate savings and serve. Repeat to make 2 more shakes.