Pulse graham crackers in a food processor until they form fine, even crumbs.
Divide the graham cracker crumbs evenly among four serving glasses to form the bottom layer.
Beat the softened cream cheese and powdered sugar in a medium bowl until the mixture is completely smooth.
In a separate chilled bowl, whisk the heavy whipping cream and vanilla extract until stiff peaks form.
Gently fold the whipped cream into the cream cheese mixture until smooth and airy.
Spoon or pipe the cheesecake mixture over the graham cracker layer in each glass.
Top each parfait with an even portion of the cherry pie filling.
Refrigerate for at least 30 minutes before serving for best results.