In the bowl of a mixer fitted with the whisk attachment, whip the heavy cream until stiff peaks form (about 5 minutes). Transfer to a new bowl; set aside.
In the bowl of your mixer fitted with the paddle attachment (no need to clean out the mixer bowl), beat the cream cheese until smooth. Slowly add sweetened condensed milk and vanilla extract. Mix until incorporated.
Slowly add the whipped cream into the cream cheese mixture, making sure not to deflate the whipped cream.
Layer a freezer-safe loaf pan with ice cream, graham cracker crumbs, and pie filling (if using), being sure to reserve some crackers and fruit for the top.
Freeze 8 hours or overnight.