Place the toasted graham cracker crumbs on a tea plate. Wet the rim of your serving glass by dipping it into the top of a glass of water, then dip the wet rim into the crumbs. Drizzle the warm caramel sauce around the glass, being sure to drizzle up and down the sides of the glass. Set aside.
In a blender, combine the vanilla ice cream, pumpkin puree, pumpkin pie spice, cinnamon, milk, and bourbon. Blend on high speed until fully combined.