As the aroma of caramelized cherries fills the kitchen, I can’t help but feel a wave of nostalgia wash over me. This Chocolate Cherry Upside Down Cake is the very embodiment of homey comfort, combining rich chocolate and the tangy sweetness of cherries in an irresistible dessert. Whipping it up is a breeze—choose between the quick chocolate cake mix version or indulge in the joy of baking from scratch, both promising a stunning centerpiece for your next gathering. Not only does this cake elevate any occasion, but it’s also perfect for that moment when you simply crave something special at home. Have you ever tasted a combination that just feels like a warm hug? Let’s dive into this delightful recipe together!

Why is this cake a must-try?
Decadent Delight: Every bite of this Chocolate Cherry Upside Down Cake offers an explosion of flavors, where the luscious chocolate perfectly complements the tart cherries.
Simplicity: Whether you’re a seasoned pro or a novice in the kitchen, this recipe provides an easy approach, allowing anyone to impress with minimal effort.
Versatile Options: Choose between a quick version using cake mix or indulge in a from-scratch creation for that authentic baking experience.
Crowd-Pleasing Appeal: Perfect for any gathering, this show-stopping dessert is bound to be the star of the table, delighting everyone from family to friends.
Serve it warm with a dollop of whipped cream or a scoop of vanilla ice cream for an extra layer of indulgence, reminiscent of the comforting sweetness found in recipes like Cinnamon Roll Cake.
Chocolate Cherry Upside Down Cake Ingredients
For the Cherry Topping
- Unsalted Butter – Adds moisture and richness to the cake and topping. Use salted butter and reduce additional salt if needed.
- Granulated Sugar – Sweetens both the cherry topping and the cake. Substitute brown sugar for a richer flavor profile.
- Tart Cherries (canned or fresh) – Provides a tart contrast to the sweet chocolate. Fresh cherries are preferable for flavor; be sure to pit them.
- Vanilla Extract – Enhances the overall flavor profile. Optional but recommended for depth of flavor.
For the Cake
- All-Purpose Flour – Gives structure to the cake. Can be substituted with gluten-free flour for a gluten-free version.
- Cocoa Powder – Contributes to the rich chocolate flavor. Use Dutch-processed cocoa for a deeper taste.
- Baking Powder – Helps the cake rise. Do not substitute with baking soda in this recipe.
- Baking Soda – Reacts with acidic ingredients for leavening. Essential alongside baking powder for proper rise.
- Salt – Enhances the flavors of the cake. Omit if using salted butter.
- Buttermilk – Adds moisture and a slight tang to the cake. Substitute with regular milk plus a tablespoon of vinegar.
- Vegetable Oil – Keeps the cake moist. Can replace with melted coconut oil or applesauce for a lighter version.
- Eggs – Provide moisture and structure. Use flax eggs for a vegan option (1 tablespoon ground flaxseed + 2.5 tablespoons water = 1 egg).
- Boiling Water – Loosens the cake batter for easier spreading and contributes to moisture.
This Chocolate Cherry Upside Down Cake is a delightful indulgence that brings comfort and nostalgia to any gathering!
Step-by-Step Instructions for Chocolate Cherry Upside Down Cake
Step 1: Prepare Cherry Topping
Preheat your oven to 350°F (175°C) and grease a 9-inch round cake pan. In a medium saucepan, melt 4 tablespoons of unsalted butter over medium heat. Stir in 1 cup of granulated sugar until dissolved, then gently fold in 2 cups of tart cherries and 1 teaspoon of vanilla extract. Cook for about 3-4 minutes until the cherries are warmed and coated in syrup, then pour this mixture into the prepared pan.
Step 2: Prepare Cake Batter
In a large mixing bowl, sift together 1 ¾ cups of all-purpose flour, 1 ¾ cups of granulated sugar, ¾ cup of cocoa powder, 1 ½ teaspoons of baking powder, 1 teaspoon of baking soda, and ½ teaspoon of salt. In another bowl, whisk together 2 large eggs, 1 cup of buttermilk, ½ cup of vegetable oil, and 1 teaspoon of vanilla extract until smooth. Gradually combine the wet and dry ingredients, mixing gently.
Step 3: Add Boiling Water
Once blended, carefully stir in 1 cup of boiling water to the cake batter. This will give your Chocolate Cherry Upside Down Cake a moist, velvety texture. Mix until just combined, ensuring there are no lumps, but be cautious not to overmix. The batter will be quite thin, which is perfect.
Step 4: Combine and Bake
Pour the chocolate batter evenly over the cherry mixture in the pan, spreading it gently to cover the cherries. Place the cake in the preheated oven and bake for 35-40 minutes. The cake is done when a toothpick inserted in the center comes out clean, and the top appears set and slightly springy to the touch.
Step 5: Cool and Invert
Once baked, remove the Chocolate Cherry Upside Down Cake from the oven and let it cool in the pan for about 10 minutes. Carefully run a knife around the edges to loosen the cake, then place a serving platter on top of the pan. Invert the cake onto the platter, allowing the cherries to rest beautifully on top. Let the cake cool completely before slicing and serving.

Chocolate Cherry Upside Down Cake Variations
Embrace your creativity and customize this delectable Chocolate Cherry Upside Down Cake to suit your taste and dietary preferences!
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Cherry Preserves: Swap tart cherries with cherry preserves for a more intense, sweet flavor that spreads beautifully.
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Nutty Crunch: Add a handful of chopped pecans or walnuts to the chocolate batter for an enticing crunch and delightful nuttiness in each bite.
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Gluten-Free: Substitute all-purpose flour with a gluten-free blend, allowing everyone to enjoy this cake without missing out on flavor or texture.
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Richer Chocolate: For an extra chocolatey experience, swirl in melted chocolate or ganache into the batter right before baking.
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Vegan Delight: Replace eggs with flax eggs (1 tablespoon ground flaxseed + 2.5 tablespoons water = 1 egg) and use almond milk instead of buttermilk for a vegan-friendly option.
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Zesty Twist: Incorporate a teaspoon of orange or lemon zest into your batter to introduce a refreshing citrus note that complements the chocolate and cherries beautifully.
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Spoonful of Spice: Add a pinch of cinnamon or a dash of cayenne pepper for a hint of warmth and complexity that takes this cake to the next level.
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Alternative Frosting: Top your cake with a light dusting of powdered sugar or a drizzle of homemade chocolate ganache for a finishing touch that makes this dessert even more irresistible.
With these variations, it’s easy to find a new favorite version of this show-stopping cake! Imagine serving a slice of this best cake at gatherings, alongside treats like No-Bake Eclair Cake or a comforting slice of Chocolate Chip Pumpkin—what a feast it would be!
How to Store and Freeze Chocolate Cherry Upside Down Cake
Room Temperature: Store the cake in an airtight container at room temperature for up to 3 days to maintain its moist texture.
Fridge: For extended freshness, place the cake in the refrigerator, where it will keep well for up to 1 week. Just ensure it’s covered to prevent it from absorbing other odors.
Freezer: To freeze, wrap the cake slices tightly in plastic wrap and then foil, or place in a freezer-safe container. It will last for up to 3 months.
Reheating: When ready to enjoy, thaw in the fridge overnight or at room temperature for a few hours, then gently reheat in the microwave or enjoy cold for a delightful treat!
What to Serve with Chocolate Cherry Upside Down Cake
There’s nothing quite like the blissful experience of pairing flavors to create a complete meal that engages all the senses.
- Whipped Cream: A dollop of fresh whipped cream adds a light, airy contrast to the rich cake, bringing harmony to your dessert experience.
- Vanilla Ice Cream: This classic topping melts into the warm cake, creating a dreamy blend of temperatures and textures that elevates every bite.
- Chocolate Sauce: Drizzling warm chocolate sauce on top enhances the cake’s chocolatey goodness and makes it an indulgent treat for chocoholics.
- Fresh Berries: The vibrant freshness of strawberries or raspberries offers a tangy complement, brightening the entire dessert with a pop of color and flavor.
- Espresso or Coffee: A hot cup of coffee or a shot of espresso cuts through the sweetness beautifully, allowing the rich flavors to shine with each sip.
- Nutty Crunch: Chopped, toasted walnuts or pecans sprinkled on top provide a satisfying crunch, adding another layer of flavor while enhancing the overall presentation.
- Chilled Sparkling Water: For a refreshing, palate-cleansing option alongside your dessert, pair it with chilled sparkling water infused with lemon or mint.
- Mascarpone Cheese: A dollop of mascarpone adds a creamy, slightly tangy element that balances the sweet notes of the cake perfectly, inviting second helpings.
- Chocolate-Covered Cherries: As a fun touch, serve these alongside to amplify the cherry essence in the cake, providing a delightful surprise of flavors.
- Espresso Martini: For the adults, a cocktail made with espresso and vodka can be a sophisticated pairing that elevates your dessert experience to a special occasion.
Make Ahead Options
Preparing the Chocolate Cherry Upside Down Cake ahead of time is a fantastic way to streamline your baking and make life easier on busy evenings! You can prepare the cherry topping up to 24 hours in advance by cooking the cherries and mixing them with sugar and butter, then simply refrigerate it until you’re ready to bake. Additionally, you can measure and mix the dry ingredients for the cake batter, storing them in an airtight container for up to 3 days. On baking day, combine the dry ingredients with the wet portion of the batter, add the boiling water, and bake as directed. This way, you can still impress your family with a homemade dessert that feels like it came from a bakery, but with half the effort!
Expert Tips for Chocolate Cherry Upside Down Cake
- Avoid Overmixing: Stop mixing as soon as the batter is combined to prevent a dense cake; a few lumps are perfectly fine.
- Preheat Properly: Always preheat your oven before baking to ensure even cooking throughout your Chocolate Cherry Upside Down Cake.
- Use Parchment Paper: Line your pan with parchment paper for easy removal and a flawless presentation of your cake.
- Check Ingredient Temperature: Use room temperature eggs and buttermilk for better mixing, enhancing the overall texture of the cake.
- Avoid Excessive Baking: Keep an eye on baking time; start checking for doneness a few minutes before the recipe states to ensure it remains moist.

Chocolate Cherry Upside Down Cake Recipe FAQs
What should I look for when selecting cherries?
Absolutely! When choosing cherries, look for ones that are firm, plump, and deeply colored. Avoid any with dark spots all over or that feel soft, as these may be overripe. If using canned cherries, ensure they are free from added sugars or preservatives for the best flavor.
How can I store leftover Chocolate Cherry Upside Down Cake?
Very! You can store the cake in an airtight container at room temperature for up to 3 days to maintain its moist texture. For longer storage, refrigerate it for up to 1 week. Just make sure it’s covered well to avoid odors from other foods in your fridge!
Can I freeze Chocolate Cherry Upside Down Cake?
Absolutely! To freeze, first let the cake cool completely, then wrap it tightly in plastic wrap followed by aluminum foil, or place it in a freezer-safe container. This will help preserve its flavor and texture. Your cake will keep well for up to 3 months. When you’re ready to enjoy it, thaw it in the fridge overnight or at room temperature for a couple of hours.
What if my cake doesn’t rise properly?
No worries! If your Chocolate Cherry Upside Down Cake doesn’t rise, it might be due to expired baking powder or baking soda. Always check the expiration dates on these leavening agents. Also, ensure that you don’t overmix your batter, as this can lead to a denser texture. Follow the instructions meticulously—keep an eye on those little details, and your cake will shine!
Is this cake suitable for pets or individuals with allergies?
I often recommend caution! Chocolate can be toxic to pets, so avoid letting them indulge in any leftover cake. As for allergies, be mindful of common allergens like eggs and dairy in this recipe. For a vegan option, use flax eggs as noted in the ingredients! Always read through the ingredients for adaptability based on allergy sensitivities.

Irresistible Chocolate Cherry Upside Down Cake to Savor
Ingredients
Equipment
Method
- Preheat your oven to 350°F (175°C) and grease a 9-inch round cake pan. In a medium saucepan, melt 4 tablespoons of unsalted butter over medium heat. Stir in 1 cup of granulated sugar until dissolved, then gently fold in 2 cups of tart cherries and 1 teaspoon of vanilla extract. Cook for about 3-4 minutes until the cherries are warmed and coated in syrup, then pour this mixture into the prepared pan.
- In a large mixing bowl, sift together 1 ¾ cups of all-purpose flour, 1 ¾ cups of granulated sugar, ¾ cup of cocoa powder, 1 ½ teaspoons of baking powder, 1 teaspoon of baking soda, and ½ teaspoon of salt. In another bowl, whisk together 2 large eggs, 1 cup of buttermilk, ½ cup of vegetable oil, and 1 teaspoon of vanilla extract until smooth. Gradually combine the wet and dry ingredients, mixing gently.
- Once blended, carefully stir in 1 cup of boiling water to the cake batter. Mix until just combined, ensuring there are no lumps, but be cautious not to overmix. The batter will be quite thin.
- Pour the chocolate batter evenly over the cherry mixture in the pan, spreading it gently to cover the cherries. Bake for 35-40 minutes until a toothpick inserted comes out clean.
- Once baked, remove the cake from the oven and let it cool in the pan for about 10 minutes. Carefully run a knife around the edges, then invert onto a serving platter.

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