Crush graham crackers in a food processor. Set aside.
In a large bowl beat the cream cheese until smooth with an electric mixer.
Add the pumpkin, vanilla, sugar, pumpkin pie spice, nutmeg and cinnamon. Beat until well combined and creamy.
Use a spatula to fold in 5 oz (1-1/2 cups) of the whipped topping; combine until no streaks remain.
Place in a piping bag or ziplock bag with a corner snipped off.
To assemble: Sprinkle 1/2 teaspoon of graham cracker crumbs on the bottom of each shot glass. Pipe a layer of pumpkin cheesecake onto the graham cracker crust (about 1 tbsp) followed by a layer of whipped topping. Repeat a second layer and finish with another sprinkle of crumbs.
Insert small spoons and refrigerate until ready to serve.
*Each shot glass has 2 tbsp pumpkin cheesecake, 1 tbsp whipped topping, 1 tsp graham cracker crumbs total.