With cooking spray, grease sides of round 9-inch springform pan that is 3-inches deep. Line side with a strip of parchment paper.
Add cream cheese to bowl of a stand mixer fitted with the whisk attachment. Whisk on medium speed until smooth, about 3 minutes.
Turn off mixer. Add heavy cream, cherry preserves, Cheerwine syrup, and kirsch to bowl, then whisk on low until incorporated. Gradually increase the speed to medium-high and whisk the mixture until it holds stiff peaks, 1-2 minutes. Scrape down sides with a spatula to fully incorporate.
Spread a layer of the whipped cream mixture on the bottom of the pan and cover with a layer of cookies, filling any gaps with broken cookies. Scatter cherries on top of cookies. Continue layering with whipped cream, cookies, and cherries, ending with a final layer of whipped cream.
Cover cake and refrigerate 6-8 hours or overnight.
Decorate with crumbled cookies and whole cherries, if desired.