Pumpkin Mixture: In a medium bowl, combine 15 ounces pumpkin puree, 14 ounces sweetened condensed milk, 8 ounces cream cheese, 2 teaspoons pumpkin pie spice, 2 teaspoons vanilla extract, and ½ teaspoon ground nutmeg. Whisk to combine until smooth - feel free to use a hand mixer, if you need to. Place in refrigerator for 30 minutes to let it cool and thicken back up.
Crust Mixture: Meanwhile, in a different medium-sized bowl combine 14 graham crackers (crushed) and ⅓ cup butter (melted). Set aside.
Make Cups: Once pumpkin mixture has thickened a bit, divide the graham cracker mixture between small glasses and press down with spoon. Add pumpkin mixture on top of that.
Serve: Enjoy with some whipped cream on top!
Notes
Dairy-Free: to make this dairy-free use a dairy-free sweetened condensed coconut milk, dairy-free butter, dairy-free cream cheese (I would recommend Kite Hill plain variety - I have the best luck with that one) and a dairy-free whipped cream.
Gluten-Free: to make this gluten-free use gluten-free graham crackers.
Make Ahead: the pumpkin mixture can easily be made a day or two ahead of time and store in the refrigerated, covered. You could fill glasses with graham cracker crust + pumpkin filling and let sit overnight and then top with whipped cream before serving.