Add the ice cream, milk, scotch, and four roasted marshmallows in a blender and lightly blend until smooth.
Lightly rub the caramel on the lip of your glasses. Place the graham cracker crumbs on a plate and press the caramel coated glass into the crumbs so they stick to the caramel.
Fill the glasses with the milkshake. Top with whipped cream and sprinkle the remaining graham cracker crumbs on top, then garnish with a roasted marshmallow.