Prepare the whipped cream by mixing the heavy cream, powdered sugar, and vanilla in a chilled bowl until stiff peaks form.
Slice the chocolate cake into bite-sized pieces, about 1-inch thick.
In a deep glass dish, start the layering process: first add a layer of chocolate cake pieces, soaking them with cherry syrup or juice.
Add a layer of pitted cherries over the cake, followed by a layer of the whipped cream mixture.
Repeat the layering process until all ingredients are used, finishing with a generous layer of whipped cream on top.
Garnish with chocolate shavings or a dusting of cocoa powder for a final touch.
Refrigerate the trifle for at least 2 hours to allow the flavors to meld and the layers to set.