Place pumpkin spice Oreos into a food processor and pulse until they turn into a fine crumb. Divide filling between 4 serving glasses or bowls and press down gently to form a crust. Set aside.
Into a large bowl, add cream cheese and beat until smooth and creamy. Add in sweetened condensed milk, molasses, vanilla, cinnamon, ginger, nutmeg, and cloves. Continue mixing until smooth. Divide the mixture evenly into 4 glasses and then chill for at least 2 hours.
When ready to serve, top with whipped cream and gingerbread men candies.