In a large bowl using a hand mixer or in the bowl of a stand mixer fitted with the paddle attachment, combine room temperature cream cheese and icing sugar until smooth and no lumps remain. Use a spatula to scrape down the sides of the bowl as necessary.
Add E.D.SMITH® Pure Pumpkin, pumpkin pie spice, vanilla pudding mix and vanilla to the bowl with the cream cheese mixture. Mix on medium high speed until well combined.
Pour in cold milk and slowly combine using the mixer on low speed. Set aside.
For the whipped cream, using a hand mixer or a stand mixer fitted with the whisk attachment, whip cold heavy cream and icing sugar on medium high speed until stiff peaks form in the whipped cream. If you accidentally over whip the cream add a little more heavy cream and gently fold together with a spatula.
Add ¾ cup of the prepared whipped cream to the bowl of pumpkin mixture and gently fold together using a spatula until no streaks of white remain being careful not to knock too much air out of the whipped cream. Set aside. Cover remaining whipped cream with plastic wrap and refrigerate until ready to assemble dessert.
Add cookies to a ziploc bag and seal then use a rolling pin to crush cookies.
To prepare the mousse, transfer mousse to a piping bag or simply spoon a layer of mousse into the bottom of your dessert cup, add a layer of crushed cookies and follow with a final layer of mousse. Transfer prepared mousse to the fridge to chill for 1-4 hours.
When you are ready to serve, top with a dollop of the remaining whipped cream and more crushed cookies. If the whipped cream has deflated, re-whip it to the desired consistency.