1 Best Decadent Chocolate Cherry Upside Down Cake You’ll Ever Taste

Name: 1 Best Decadent Chocolate Cherry Upside Down Cake You'll Ever Taste
Prep time: 15 min
Cook time: 40 min
Total time: 55 min
Cuisine: American
Ingredients: 1 cup all-purpose flour; 1/2 cup cocoa powder; 1 tsp baking powder; 1/2 tsp baking soda; 1/4 tsp salt; 1/2 cup unsalted butter, softened; 3/4 cup granulated sugar; 2 large eggs; 1 tsp vanilla extract; 1/2 cup buttermilk; 1 can (21 oz) cherry pie filling

Author: lia

Published: August 7, 2025

Updated: August 7, 2025

Decadent Chocolate Cherry Upside Down Cake for Fall

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There’s something magical about the first crisp autumn breeze that sends me straight to the kitchen. I start craving cozy desserts that fill the house with warmth and bring everyone together. That’s how this decadent chocolate cherry upside down cake for fall became my go-to recipe – it’s like wrapping yourself in a delicious hug!

I’ll never forget the first time I experimented with this combination. My grandmother always made classic pineapple upside down cake, but one rainy October afternoon, I found myself staring at a jar of cherries and thought “what if…” The result? Pure magic. The tart cherries caramelize into a glossy topping that perfectly balances the rich chocolate cake underneath. It’s become our family’s new fall tradition – we make it for Sunday dinners, potlucks, and whenever we need a little extra comfort.

What makes this recipe special is how the cherries’ natural sweetness plays against the deep cocoa flavor. It’s fancy enough for company but simple enough for weeknight baking. Just wait until you see those ruby-red cherries peeking through the dark chocolate cake when you flip it – it’s downright showstopping!

Table of Contents

Why You’ll Love This Decadent Chocolate Cherry Upside Down Cake for Fall

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Trust me, this isn’t just another cake recipe – it’s the kind of dessert that makes people ask for seconds and beg for the recipe. Here’s why it’s become my autumn baking obsession:

That perfect chocolate-cherry magic: The sweet-tart cherries caramelize into this gorgeous glaze that seeps into every bite of rich chocolate cake. It’s like black forest cake’s elegant cousin!
Foolproof preparation: No fancy techniques here – just simple mixing and pouring. Even if you’re baking while distracted (kids, pets, whatever!), this cake comes out perfect.
Instant crowd-pleaser: I’ve brought this to everything from book club to Thanksgiving, and it always disappears first. That dramatic flip when you turn it out? Pure kitchen theater.
Cozy fall vibes: The warm cocoa scent filling your kitchen is basically autumn in cake form. Pair it with coffee or cider for maximum hygge.

Ingredients for Decadent Chocolate Cherry Upside Down Cake for Fall

Now, let’s talk ingredients – because the magic starts with quality stuff! This isn’t one of those “throw whatever’s in your pantry together” recipes. Each component plays a special role in creating that perfect chocolate-cherry harmony. Here’s what you’ll need:

1 cup all-purpose flour: Spoon and level it, friends! No packing the measuring cup or you’ll end up with a dry cake.
1/2 cup cocoa powder: Use natural, not Dutch-process for that deep chocolate flavor. My secret? I always sift it to avoid lumps.
1 tsp baking powder + 1/2 tsp baking soda: Our dynamic rising duo – don’t mix them up!
1/4 tsp salt: Trust me, it makes the chocolate taste more chocolatey.
1/2 cup unsalted butter, softened: This means left out until your finger leaves a slight indent – about 1 hour. Don’t microwave it! (I’ve made that mistake…)
3/4 cup granulated sugar: Regular white sugar works best for that perfect crumb.
2 large eggs: Not extra-large, not jumbo – large. Room temp eggs mix in smoother.
1 tsp vanilla extract: The good stuff, please! Imitation vanilla has no place here.
1/2 cup buttermilk: No buttermilk? Make your own with 1/2 cup milk + 1/2 Tbsp lemon juice. Let it sit 5 minutes.
1 can (21 oz) cherry pie filling: The star of our upside-down show! I like the kind with extra cherries.

Equipment You’ll Need

Don’t worry – you won’t need any fancy gadgets for this cake! Here’s my simple toolkit:

9-inch round cake pan: My grandma swore by aluminum pans – they distribute heat perfectly. If you only have glass, reduce oven temp by 25°F.
Mixing bowls: One large for wet ingredients, one medium for dry.
Rubber spatula: Essential for scraping every bit of that delicious batter!
Whisk: A simple wire whisk blends dry ingredients better than a spoon.
Cooling rack: Let’s the cake breathe before the big flip.

That’s it! No stand mixer required (though you can use one if you prefer).

How to Make Decadent Chocolate Cherry Upside Down Cake for Fall

Okay, here’s where the magic happens! I’ll walk you through each step like I’m right there in the kitchen with you – apron on, oven preheated, and ready for some seriously delicious baking therapy.

Preparing the Cherry Layer

First, let’s get that gorgeous cherry topping ready! Generously grease your cake pan with butter – like you’re frosting it with love. Then pour in that beautiful cherry pie filling. Use the back of a spoon to spread it evenly across the bottom. Don’t stir it too much or you’ll break up those plump cherries! Just a gentle smoothing is all it needs. This layer is going to caramelize into sticky-sweet perfection while baking.

Mixing the Chocolate Batter

Now for the chocolatey goodness! In a large bowl, cream together the softened butter and sugar until it’s light and fluffy – about 3 minutes with a hand mixer. This is KEY for that perfect cake texture! Add eggs one at a time, letting each incorporate fully before adding the next. Then mix in the vanilla.

Here’s my grandma’s trick: alternate adding the dry ingredients (flour, cocoa powder, etc.) with the buttermilk, starting and ending with dry. Mix just until combined after each addition – overmixing makes tough cake! The batter should be thick but pourable, like melted chocolate pudding.

Baking and Inverting the Cake

Carefully pour the batter over your cherry layer – it’ll seem thick, but trust me, it spreads beautifully in the oven. Bake at 350°F for 35-40 minutes. When a toothpick comes out with just a few moist crumbs (not wet batter), it’s done!

Now the hardest part: WAIT 10 minutes before flipping! This lets the cake set so it doesn’t fall apart when inverted. Run a knife around the edges, place your serving plate on top, and confidently flip it over. Peel off the pan slowly – that reveal of glossy cherries peeking through dark chocolate is pure baking bliss!

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Tips for Perfect Decadent Chocolate Cherry Upside Down Cake for Fall

After making this cake more times than I can count (okay fine, it’s my excuse to eat dessert for “recipe testing”), I’ve picked up some foolproof tricks:

Check early, check often: Start testing at 30 minutes – ovens vary wildly. That toothpick should have a couple moist crumbs, not be clean!
Fresh cherry upgrade: In summer, swap pie filling for 2 cups pitted fresh cherries tossed with 1/4 cup sugar and 1 Tbsp cornstarch.
The flip factor: If cherries stick, just scrape them off the pan and pat them back onto the cake – no one will know!
Butter matters: If your cake seems dry, you probably didn’t cream the butter/sugar long enough. Set a timer next time!
Patience pays: Let it cool completely before slicing – I know it’s hard, but the texture improves as it sets.

Oh, and if it cracks when flipping? Call it “rustic charm” and drown it in whipped cream!

Variations and Serving Suggestions

This cake is downright divine as-is, but here’s how I like to mix it up sometimes:

Nutty twist: Fold 1/2 cup chopped pecans or walnuts into the batter for extra crunch. My uncle swears by toasted almonds on top!
Boozy upgrade: Add 1 Tbsp bourbon to the cherry layer for adult gatherings – it deepens the flavors beautifully.
Ice cream pairing: Serve warm slices with vanilla bean ice cream melting over that cherry topping. (My weakness!)
Breakfast version: Swap half the sugar for maple syrup and call it a “coffee cake” – I won’t tell!

Pro tip: Leftovers? Pop a slice in the microwave for 10 seconds – tastes like fresh-baked all over again!

Storage and Reheating Instructions

This cake keeps beautifully – if it lasts that long! Here’s how I handle leftovers (though in my house, that’s rare):

Room temp storage: Just cover it loosely with foil or a cake dome. It’ll stay fresh and moist for 2 days – any longer and the cherries start weeping.
Reviving leftovers: A quick 15-second zap in the microwave brings back that fresh-baked magic. Or place a slice in a 300°F oven for 5 minutes to crisp up the edges.
Freezing tip: Wrap individual slices tightly in plastic, then foil. Thaw overnight in the fridge when cravings strike!

Pro tip: The cherry topping gets stickier and more decadent by day two – no judgement if you “accidentally” leave it out on purpose!

Nutritional Information

Okay, let’s be real – we’re not eating cake for its health benefits! But here’s the nutritional breakdown (per slice) for those curious minds or dietary needs. Remember, these are estimates – actual numbers vary based on your specific ingredients and slice size. My philosophy? One heavenly bite is worth every calorie!

Calories: About 320 per serving
Fat: 12g (7g saturated – blame the good butter!)
Carbs: 48g (28g sugar – mostly from those luscious cherries)
Protein: 5g (Eggs and buttermilk doing their thing)

Now go enjoy your cake – life’s too short to obsess over numbers when chocolate’s involved!

Frequently Asked Questions

Can I use frozen cherries instead of pie filling?
Absolutely! Thaw 2 cups of frozen cherries first, then toss them with 1/4 cup sugar and a tablespoon of cornstarch. The juices will thicken beautifully as it bakes – just like jam!

Help! I don’t have buttermilk – what can I use?
No panic needed! Mix 1/2 cup regular milk with 1/2 tablespoon lemon juice or vinegar and let it sit for 5 minutes. It’ll thicken up and work just as well. Yogurt thinned with milk works too in a pinch.

Can I make this cake ahead and freeze it?
You bet! Bake and cool completely, then wrap tightly in plastic and foil. Freeze for up to 3 months. Thaw overnight in the fridge, then warm slightly before serving. The cherries might weep a bit, but the flavor stays amazing.

Would this work in a cast iron skillet?
Ohhh yes – and it’s magical! Preheat your 10-inch skillet with the cherry layer for 5 minutes before adding batter. The edges get wonderfully crispy. Just reduce baking time by about 5 minutes.

Can I substitute the cocoa powder?
If you must, use melted chocolate instead – about 3 oz of semisweet. But honestly? Stick with cocoa powder if you can. It gives that perfect crumb texture Dutch-process cocoa can’t match!

Nothing makes me happier than seeing your chocolate cherry masterpieces! Snap a photo of that gorgeous flip moment and tag me – I’ll probably squeal louder than you did when it came out perfect. Leave a review if this becomes your new fall favorite too (secret: I read every single one while nibbling leftover crumbs!). You can also find more delicious recipes on our Pinterest page.