Break the cookies into small chunks and set aside.
Pour condensed milk, vanilla and cinnamon into a small bowl. Add in a couple tablespoons of pie filling. Stir until mixed.
In a large bowl, beat whipping cream, with an electric mixer, until soft peaks form.
Soften the condensed milk mixture by adding a dollop of whipped cream and stir until blended. This will make it easier to fold it in the whipped cream.
Pour the condensed milk mixture into the bowl with the whipped cream. Gently fold in the whipped cream.
Layer whipped cream mixture, cookie pieces and pie filling in a standard size loaf pan. Start with half the whipped cream, sprinkle half the cookies next and add dollops of pie filling. Gently swirl the cookies and pie filling into the whipped cream. Repeat with the remaining ingredients.
Place plastic wrap directly on the surface of the mixture to prevent crystals. Freeze until firm, at least 6 hours. Overnight is better.
When firm, serve with fresh peach slices and a shortbread cookie.