For the apples:
Place butter in small skillet and melt over medium heat.
Add apples, brown sugar, flour and cinnamon and stir to combine. Cook over medium-high heat, stirring frequently, until the mixture is bubbly. Then reduce heat to medium and continue cooking for about 5 minutes until mixture has thickened. Set aside to cool.
For the graham cracker crust:
Combine graham cracker crumbs and butter in a small bowl. Set aside.
For the cheesecake:
Using electric mixer on medium speed, beat cream cheese, sugar, cream and vanilla until thoroughly combined and smooth.
For the cinnamon whipped cream:
Place cream in cold mixing bowl. Using electric mixer with whisk attachment, beat at medium-high speed until cream begins to thicken.
Sprinkle sugar and cinnamon over cream and continue beating until soft peaks form.
To assemble the cheesecakes:
Place 2 to 3 tablespoons of cheesecake in bottom of four 8-ounce glasses, spreading evenly. For tapered glasses like the ones pictured here, you may want to use a bit less cheesecake for bottom layer.
Top each with about 2 tablespoons graham cracker mixture. You will have some of this mixture left over for garnish.
Divide remaining cheesecake among glasses and spread gently on top of graham crackers.
Place apples on top of cheesecake, dividing evenly among the glasses.
Place dollop of whipped cream on top of each dessert and garnish with the remaining graham cracker mixture. Add whole graham crackers as an additional garnish, if you like.
Serve immediately, or chill for at least 2 hours for a firmer cheesecake.