Chocolate Cherry Upside Down Cake: 5 Easy Tricks for Success

Name: Chocolate Cherry Upside Down Cake: A Showstopper That’s Surprisingly Easy
Prep time: 20 min
Cook time: 40 min
Total time: 1 h
Cuisine: American
Ingredients: 2 cups pitted tart cherries (fresh or frozen); ½ cup granulated sugar (for topping); ¼ cup unsalted butter; 1 tsp vanilla extract (for topping); 1 ½ cups all-purpose flour; 1 cup granulated sugar; ½ cup unsweetened cocoa powder; 1 tsp baking powder; 1 tsp baking soda; ½ tsp salt; 2 large eggs (room temp); 1 cup buttermilk; ½ cup vegetable oil; 1 tsp vanilla extract (for batter); ¾ cup boiling water

Jump to Recipe

There’s something magical about flipping a cake out of a pan and revealing that glistening, jammy fruit layer underneath. As a kid, I thought upside-down cakes were some kind of baking sorcery. Turns out, with the right ingredients and a little technique, they’re one of the easiest ways to impress.

This Chocolate Cherry Upside Down Cake is rich, bold, and balanced—sweet, tart cherries on top of (well, technically below) a moist, dark chocolate cake. This one’s for folks who want drama on the plate but calm in the kitchen.

For the Cherry Topping

You’ll need:

Pitted tart cherries (fresh or frozen, about 2 cups)
½ cup granulated sugar
¼ cup unsalted butter
1 tsp vanilla extract

Tip: Tart cherries are key. They cut through the richness. If you use sweet cherries, dial back the sugar a bit.

For the Chocolate Cake Batter

Dry ingredients:

1 ½ cups all-purpose flour
1 cup granulated sugar
½ cup unsweetened cocoa powder
1 tsp baking powder
1 tsp baking soda
½ tsp salt

Wet ingredients:

2 large eggs (room temp)
1 cup buttermilk
½ cup vegetable oil
1 tsp vanilla extract
¾ cup boiling water

Frank tip: That boiling water? It “blooms” the cocoa. You want that deep, complex flavor—not flat chocolate.

How to Make the Chocolate Cake Layer

Step 1: Prepare the Cherry Topping

Preheat your oven to 350°F (175°C). Always start with a hot oven—no excuses.

Line a 9-inch round cake pan with parchment paper and grease the whole thing, bottom and sides.

In a saucepan, combine tart cherries, sugar, and butter. Simmer over medium heat for about 8–10 minutes, until the juices thicken a bit. Take it off the heat, stir in the vanilla.

Pour the mixture into your prepped pan and smooth it out evenly. That’s your cake’s crown—make it nice.

Step 2: Make the Chocolate Cake Batter

Whisk together the dry stuff: flour, sugar, cocoa, baking powder, baking soda, and salt.

In another bowl, mix the eggs, buttermilk, oil, and vanilla.

Combine wet and dry—just until blended. Don’t overmix.

Slowly add boiling water while stirring. Batter will be thin—perfect.

Pour gently over the cherry layer. Smooth the top and tap the pan to settle it.

Step 3: Bake the Cake

Bake at 350°F for 35–40 minutes. Toothpick should come out clean or with crumbs.

Cool in the pan for 15 minutes, then flip onto a plate. Do it while warm so the cherries don’t stick.

Step 4: Serve and Enjoy

Glossy chocolate cherry upside down cake topped with fresh herbs

Serve warm or room temp.

Top with whipped cream, ice cream, or mint if you’re feeling fancy.

Mistakes to Avoid

Overmixing – Builds gluten. You want tender, not chewy.
Not preheating the oven – You’ll throw off the rise.
Skipping parchment – Rookie mistake. Cherries will stick and tear.
Using cold eggs or buttermilk – Brings down the batter temp. Room temp blends better.

Tips and Tricks

Boost cherry flavor with 1 tbsp cherry liqueur in the topping.
Add crunch with chopped almonds or hazelnuts in the cherry layer.
Extra chocolate? Swirl in ¼ cup melted chocolate into the batter.
Finish with flair: dust with cocoa powder or add chocolate curls on top.

If you enjoy fruit-forward desserts, don’t miss this bourbon peach upside-down cake.

This chocolate cherry cake rivals even a moist chocolate zucchini cake in richness.

For another delightful combination, try these banana chocolate chip cookies.

This cherry upside-down cake also pairs well with fruity options like a peach cobbler trifle.

Need something creamier? Try these dulce de leche cheesecake bars.

For fruit-lovers, this strawberry shortcake in sheet pan style is equally crowd-pleasing.

Why You’ll Love This Cake

Benefit	Why It Matters
Bold Flavor Combo	Tart cherries and rich chocolate create a perfect sweet-tangy balance
Impressive Presentation	That glossy cherry top makes it look bakery-level fancy—no frosting needed
Easy Ingredients	Mostly pantry staples—no trips to specialty stores required
Beginner-Friendly Technique	Simple steps, minimal equipment—great for novice bakers
Moist, Tender Crumb	Boiling water + buttermilk = insanely soft texture
Make-Ahead Friendly	Tastes even better the next day—ideal for prepping in advance
Crowd-Pleaser	Works for birthdays, dinner parties, holidays, or just because
Versatile Garnishing	Whipped cream, ice cream, or mint? Go as basic or as bougie as you like

FAQ: Chocolate Cherry Upside Down Cake

Can I use fresh cherries?

Yes—just pit them first. You might need to simmer a little longer to thicken the topping.

Can I substitute buttermilk?

Absolutely. Mix 1 tbsp lemon juice or vinegar into 1 cup of milk and let it sit for 5 minutes.

How to check for doneness?

Toothpick test—insert in the center. Clean or a few crumbs = done.

How to ensure even cherry layer?

Level the cherries with a spatula before adding batter. Tap the pan gently to settle it.

Conclusion: Flip It, Slice It, Love It

This Chocolate Cherry Upside Down Cake is rich, balanced, and striking to look at—like a dessert with attitude. It’s simple enough for a weeknight, fancy enough for a dinner party. Get those cherries bubbling, bloom that cocoa, and don’t be afraid of the flip. You’ve got this.

Want more crave-worthy recipes like this? Visit my Pinterest page for more sweet inspiration, tips, and kitchen wins.

Chocolate Cherry Upside Down Cake: A Showstopper That’s Surprisingly Easy

Table of Contents

For the Cherry Topping