Add the vanilla ice cream, peaches, milk, cinnamon, and vanilla extract to a blender. Tip: For a thicker shake, freeze the peaches for 30 minutes first.

Blend on high speed until smooth and creamy, about 30-45 seconds. Tip: If the shake is too thick, add 1-2 tbsp more milk.

Pour into tall glasses and garnish with graham cracker crumbs if desired. Tip: For extra flair, rim the glasses with crushed graham crackers.