To make the whipped cream, place the whipping cream in the bowl of an electric mixer fitted with the whisk attachment. Beat on high speed until the mixture starts to thicken. Add the powdered sugar and vanilla and continue to beat until stiff peaks form. Refrigerate until ready to use.
Combine the apples, cinnamon, butter, and brown sugar in a small sauce pan over medium heat. Cook, stirring occasionally, until apples are softened, about 5 minutes.
To assemble, place about 10 gingersnaps side by side in a circle then fill in the middle with additional cookies (I used 14 total cookies on my first layer).
Spread a thin layer of whipped cream over the cookies. This first layer is a little difficult because the cookies want to slide around, but just keep pushing them back together until you get the first layer down. From here on out, it's smooth sailing! Each whipped cream layer should be thick enough so that no cookie shows underneath.
Top the whipped cream with a 1/3 of the apple mixture followed by another layer of whipped cream. Repeat this pattern twice- cookie, whipped cream, apple, whipped cream.
On the last layer, I like to just pile the whipped cream in the center and place two gingersnaps in the middle to set it off. Refrigerate for at least 2 hours or overnight then slice and serve.