Preheat oven to 350ºF. Grease and flour 2 round 8-inch cake pans. Line with parchment paper if desired for easy removal.
Place the flour, sugar, cocoa, baking powder, baking soda and salt in a bowl and whisk together. 1 3/4 cups all-purpose flour, 1 3/4 cups granulated sugar, 3/4 cup unsweetened cocoa powder, 1 teaspoon baking powder, 2 teaspoons baking soda, 1 teaspoon salt
In a stand mixer, mix the buttermilk, oil, eggs, vanilla together. Slowly add in the mix of dry ingredients while the mixer is on low. Add the coffee and make sure everything is combined. The batter will be very thin. 1 cup buttermilk, 1/2 cup canola oil, 2 large eggs, 1 teaspoon vanilla extract1 cup freshly brewed strong hot coffee
Pour the batter into the prepared pans and bake for 28-30 minutes or until a toothpick inserted in the middle comes out clean.
Allow the cakes to cool on a wire rack for 10 minutes. Turn the cakes out onto a cooling rack. Once the cakes are cooled, use a serrated knife to slice each cake layer in half so you end up with 4 layers. Crumble one layer into cake crumbs. These crumbs will be used to decorate the cake.
Make the Cherry Filling:
While the cake is baking, prepare the cherry filling. Drain the cherries but reserve ¼ cup cherry juice. 30 ounces pitted sour cherries
To a 2 quart saucepan, add the cherries, reserved juice, granulated sugar and cornstarch. Set to medium-low heat. Cook and stir until slightly thickened (about 3-5 minutes). 1 cup granulated sugar, 1/4 cup cornstarch
Stir in the vanilla extract and butter. Mix until the butter is melted. Set the cherries aside to cool completely. 1 teaspoon vanilla extract, 1 tablespoon salted butter
Make the Whipped Cream Frosting:
Chill the metal bowl of a stand mixer with the whisk attachment (or a large metal bowl to use with a hand mixer) for at least 5 minutes.
Add the heavy cream and powdered sugar to the bowl. Beat on high speed for 3-5 minutes or until stiff peaks form. Place the frosting in the refrigerator until you are ready to assemble the cake. 3 cups cold heavy whipping cream, 1/3 cup powdered sugar
To Assemble the Cake:
Place one chocolate cake cake layer down on a cake plate. Top with 1 cup of whipped topping. Spread to cover the cake.
Spread ¾ cup cooled cherry filling over the whipped cream. Place a 2 layer of cake on top of the cherries.
Repeat with another cup of whipped cream, ¾ cup of cherry topping and third cake layer.
Frost the entire outside of the cake with the whipped frosting, setting aside about 1 ½ cups for making dollops of frostings around the top. Press the crumbled cake crumbs onto the bottom half of the cake all around the sides.
Spoon the remaining cherry filling on top of the cake to about 1" from the edge.
Place the reserved whipped frosting into a large decorating bag with a Wilton 1M tip. Squeeze stars around the outer top edge of the cake. Sprinkle the cake with shaved milk chocolate. 1/4 cup shaved milk chocolate
Refrigerate immediately until serving. Store any leftovers in the refrigerator in a covered cake container.
Notes
Serve within 4 hours of assembling the cake. The whipped cream may start deflating, making the cake hard to slice.
Make the cake and cherry filling in advance, then whip the cream and assemble the day you want to serve it.
Top with fresh cherries if you'd liek.
The calories shown are based on the cake being cut into 15 pieces (all of the frosting and cherry filling used), with 1 serving being 1 slice of cake. Since different brands of ingredients have different nutritional information, the calories shown are just an estimate.