When you flip this stunning cake out of its pan, you’ll reveal a glossy crown of deep red cherries nestled in rich, caramelized syrup that cascades down the sides of moist chocolate cake. This Chocolate Cherry Upside Down Cake takes the classic pineapple version and elevates it to new heights with the irresistible combination of dark chocolate and sweet-tart cherries. The result is a dessert that’s both rustic and elegant, with each slice revealing beautiful jewel-toned cherries suspended in a tender, cocoa-rich cake that practically melts in your mouth.
Serves: 10-12 people
What You’ll Need for the Topping
- 1/4 cup unsalted butter
- 2/3 cup packed light brown sugar
- 2 tablespoons corn syrup or honey
- 2 pounds fresh sweet cherries, pitted (or 3 cups frozen, thawed)
- 2 tablespoons cherry juice or water
- 1 tablespoon vanilla extract
What You’ll Need for the Cake
- 1 3/4 cups all-purpose flour
- 3/4 cup unsweetened cocoa powder
- 1 1/2 cups granulated sugar
- 1 1/2 teaspoons baking powder
- 1 teaspoon baking soda
- 1 teaspoon salt
- 1 cup buttermilk
- 1/2 cup vegetable oil
- 2 large eggs
- 1 cup hot coffee or hot water
- 2 teaspoons vanilla extract
Preparing Your Pan
Start by preheating your oven to 350°F. Use a 10-inch round cake pan or cast iron skillet for the best results. The heavy bottom helps create an even caramelization. Grease the sides of your pan well with butter, but don’t grease the bottom since the topping will prevent sticking.
Creating the Stunning Topping
Place the butter, brown sugar, and corn syrup in your cake pan and put it directly on the stovetop over medium heat. Stir constantly until the butter melts and the mixture starts to bubble and caramelize, about 3-4 minutes. Remove from heat and quickly arrange the pitted cherries in a single layer over the caramel mixture, packing them in snugly. Drizzle with cherry juice and vanilla extract. The cherries should cover the entire bottom of the pan in an attractive pattern.
Making the Rich Chocolate Cake
In a large mixing bowl, whisk together the flour, cocoa powder, granulated sugar, baking powder, baking soda, and salt until no lumps remain. In a separate bowl, combine the buttermilk, vegetable oil, eggs, and vanilla extract, whisking until smooth. Pour the wet ingredients into the dry ingredients and stir until just combined.
The Secret to Moist Cake
Slowly pour in the hot coffee while stirring continuously. The batter will be quite thin, but this is exactly what creates the incredibly moist texture. The hot liquid helps bloom the cocoa powder and creates a deeper chocolate flavor. Don’t worry if the batter seems thinner than typical cake batter – this is perfectly normal for this recipe.
Assembly and Baking
Carefully pour the chocolate batter over the cherries in the pan, spreading it gently with a spatula to cover all the fruit. The batter should completely cover the cherries without disturbing their arrangement. Bake for 50-60 minutes, or until a toothpick inserted into the cake portion comes out with just a few moist crumbs attached.
The Dramatic Flip
This is the most exciting part! As soon as the cake comes out of the oven, run a knife around the edges to loosen any spots that might be sticking. Place a large serving plate upside down over the cake pan. Using oven mitts, quickly and confidently flip the whole thing over in one smooth motion. Let the pan sit upside down on the plate for 2-3 minutes before carefully lifting it off.
Finishing Touches
If any cherries stick to the pan, simply scoop them out and arrange them back on top of the cake. The caramelized syrup will continue to soak into the cake as it cools, creating layers of flavor throughout. Let the cake cool for at least 15 minutes before serving to allow the flavors to settle.
Serving Suggestions
This cake is beautiful on its own, but a dollop of lightly sweetened whipped cream or a scoop of vanilla ice cream makes it even more special. The contrast between the warm cake and cold cream is absolutely divine. For an adult twist, try serving it with a small glass of cherry liqueur or red wine.
Tips for Perfect Results
Fresh cherries work best, but if you’re using frozen ones, make sure they’re completely thawed and drained to prevent excess moisture. Don’t skip pitting the cherries – biting into a pit can ruin the experience. If you don’t have a cherry pitter, a clean paperclip works surprisingly well for removing pits from small batches.
Make-Ahead Magic
This cake actually improves after sitting for a few hours as the cherry juices soak into the chocolate cake. You can make it up to a day ahead and store it covered at room temperature. If you need to reheat it, warm individual slices gently in the microwave for 10-15 seconds.
Why This Combination Works
The natural tartness of cherries perfectly balances the rich sweetness of chocolate, while the caramelized brown sugar adds depth and complexity. The upside-down method ensures that every bite gets the perfect ratio of fruit to cake, with the cherry juices creating natural moisture throughout the dessert.
