1. To make freshly whipped cream: With a hand mixer or in the bowl of a stand mixer, whip 2 cups of heavy cream until it just holds soft peaks. Add 1/3 cup of powdered sugar, 1/2 teaspoon of vanilla extract (optional) and whip to combine until stiff peaks hold. Do not overmix. Set aside 1/2 cup whipped cream for topping.
2. In a separate large bowl, beat the cream cheese until smooth. Fold in the 3 cups of whipped cream or Cool Whip.
3. Assemble the cake: Spread a thin layer of the cream mixture in a 8 x 8 pan to coat the bottom.
4. Place 3 graham crackers across the center of pan and then break up 1 or 2 more crackers as needed to fill in the gaps. Spread half of the cream mixture on top. Spoon an even layer of cherry pie filling and spread.
5. Top with another layer of graham crackers, breaking them as needed to make them fit. Spread the remaining cream mixture over top. Add another layer of cherry pie filling.
6. Top with the final layer of graham crackers. Spread the reserved 1/2 cup freshly whipped cream (or Cool Whip) over evenly.
7. Arrange the last layer of the cherry pie filling evenly. Sprinkle on graham cracker crumbs on top.
8. Refrigerate for at least 4 hours or overnight until the graham crackers have softened completely. Serve chilled and dust with powdered sugar if desired.

For the Homemade Cherry Pie Filling:

1. In a saucepan over medium heat, simmer cherries (stirring often) for 10 to 15 minutes, until they release their juices. Whisk in honey or sugar until dissolved.

2. In a separate bowl, whisk together cornstarch with water until smooth and whisk into the saucepan. Turn heat to medium-high and cook until the filling has thickened, about 2 minutes; remove from heat, let cool, and use as pie filling.