In a medium mixing bowl, beat together the pumpkin puree, cream cheese, brown sugar and pumpkin pie spice.
In a separate bowl, beat the heavy cream with the granulated sugar and vanilla vinegar to medium peaks
Fold three-quarters of the whipped cream into the pumpkin mixture, reserving one quarter for topping.
Using a pastry brush, brush lady fingers with espresso vinegar and layer the bottom of 8 dessert glasses. Top with filling. Repeat layer. Top with reserved whipped cream.
Refrigerate at least 1 hour. When ready to serve, sprinkle with a little more pumpkin pie spice and crushed amaretti cookies.