Cut 3 marshmallows in half and place sticky side down along the inside of a glass. Set aside.
In a medium-sized bowl, whip the heavy cream, marshmallow fluff and vanilla together and set aside.
Set oven to broil on low and brown the last three marshmallows. Remove from oven.
In a blender, blend together the milk, chocolate sauce, toasted marshmallows and chocolate ice cream until well-mixed.
Drizzle some Hershey's syrup around the insides of the glass.
When filling the glass, alternate with the ice cream mixture and the marshmallow mixture - starting first with the ice cream and ending with the marshmallow mixture.
Top the milkshake off with the chopped Hershey's pieces and sprinkle on the crushed graham crackers.
Notes
Broiling the marshmallows will take under a minute. Make sure to watch them closely. I broiled mine with the door open so I could pull them out quickly.