Beat the whipping cream in a stand mixer fitted with the whisk attachment. Beat until stiff peaks form. Set aside.
Add cherry pie filling to a medium bowl. Crush slightly with a potato masher. Add sweetened condensed milk and vanilla and stir. Pour into whipped cream and gently fold to combine.
Divide filling between two pie crusts. Cover tightly with plastic wrap and freeze for at least 4 hours before serving.
Drizzle with chocolate sauce or hot fudge and top with whipped cream and cherries before serving.