Step 1: Prepare your ingredients. Crumble the chocolate cake into bite-sized pieces. If making whipped cream from scratch, ensure your heavy cream, bowl, and whisk are very cold.
Step 2: Make the vanilla whipped cream. In a large mixing bowl, combine heavy whipping cream, powdered sugar, and vanilla extract. Beat with an electric mixer on medium-high speed until stiff peaks form. Be careful not to overbeat.
Step 3: Assemble the trifle. In a large trifle dish or clear glass bowl, create layers. Start with a layer of crumbled chocolate cake at the bottom.
Step 4: Spoon half of the cherry pie filling over the cake layer, spreading it evenly.
Step 5: Add a generous layer of the prepared whipped cream over the cherry filling.
Step 6: Repeat the layers: another layer of chocolate cake, followed by the remaining cherry pie filling, and then top with the rest of the whipped cream.
Step 7: Decorate your trifle. For an extra festive touch, garnish with fresh cherries, chocolate shavings, or a sprinkle of cocoa powder.
Step 8: Chill the trifle. Cover loosely with plastic wrap and refrigerate for at least 2 hours to allow the flavors to meld and the cake to absorb some moisture, making it incredibly tender.