Chocolate Pear Upside Down Cake

A moist, easy-peasy fudgy chocolate cake is baked atop a layer of caramelized pears. Once ready, the cake is flipped over and the fruit crowns the cake!

Well, what do you know: it is a new recipe for chocolate pear upside down cake – part of my oil-based baking series with Colavita Olive Oil  – and I could not be more excited about it. I adore partnering with Colavita on the series because oil-based baked goods are my jam (obvs). And this week’s recipe is particularly exciting to me because it involves CHOCOLATE CAKE, which is basically my everything. Said cake is also of the upside-down variety, which is also something I’m fond of, as upside-down cakes are topped with caramelized fruit (in this instance, pears) and who doesn’t like the sound of something “caramelized?” One of my most fave caramelized fruit cakes is this banana upside down cake, and it was one of the first I ever made (okay, it WAS the first I ever made) and I haven’t looked back since.

chocolate pear upside down cake

Now, not everyone appreciates the idea of fruit and chocolate and honestly, I might be one of those people. But I make an exception when the fruit is pear and hopefully you will, too. Pear has a mild flavor that marries beautifully with the fudgy chocolate of this cake. It is also a soft fruit that all but collapses once caramelized and literally sinks into the top of the cake, making for a super luscious cake topping. 

chocolate pear upside-down cake

The cake is assembled in a single bowl (and a glass measuring cup) and comes together quickly and easily. The pears are caramelized in the skillet that you bake the cake in (bringing the concept of one bowl to a whole new level) but if you do not have a 10-inch cast iron or oven-proof skillet, you can make the cake in a 10-inch cake pan – melt the butter and sugar in the pan in the oven, rather than on the stove-top. Slicing the pears super thin means you get to add loads of extra slices and they still all collapse into something quite luxurious that (eventually) tops your pie. Upside down cakes start with the fruit and caramel on the bottom and the cake on top – but after baking the cake is flipped and the fruit crowns the cake in all the best ways. Also, you can watch me make this chocolate pear upside down cake on IGTV . . . 

Print Pin
4.75 from 4 votes

Chocolate Pear Upside Down Cake

A moist, easy-peasy fudgy chocolate cake is baked atop a layer of caramelized pears. Once ready, the cake is flipped over and the fruit crowns the cake!
Recipe Author Jessie Sheehan
Course Dessert
Cuisine American
Prep Time 20 minutes
Cook Time 25 minutes
Total Time 45 minutes
Servings 8


  • For the caramelized pears:
  • 1/4 cup  unsalted butter
  • 1/2 cup  light brown sugar
  • 1/4  teaspoon  kosher salt
  • 1/2 teaspoon vanilla
  • 2 – 3  pears peeled and cored
  • For the cake:
  • 1 cup all-purpose flour
  • 5 tablespoons Dutch-process cocoa powder
  • 1 cup packed light brown sugar
  • 3/4 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon kosher salt
  • 1/2 cup whole milk
  • 1/4 cup Colavita Olive Oil
  • 1 large egg
  • 1 large egg yolk
  • 2 teaspoons pure vanilla extract
  • 1 teaspoon espresso powder
  • 1/2 cup hot water


  • Preheat the oven to 350°F.
  • To prepare the pears, cut the pears into 1/8 to 1/4-inch slices. Melt the butter in a 10-inch cast iron skillet over medium heat. Add the brown sugar and salt and cook until melted, stirring occasionally. Remove from the heat, add the vanilla and stir to combine.
  • Decoratively place the pear slices onto the caramel, overlapping them as you do, and starting with a circle of pears in the center, fanning them out as you go. Though, really, however you place them will be both pretty and delish.
  • To make the cake, add the flour, cocoa powder, sugar, baking powder, baking soda and salt to a large mixing bowl and whisk to combine.
  • Combine the milk, oil, egg, yolk and vanilla in large glass measuring cup and whisk to combine. Pour over the dry ingredients and fold with a flexible spatula until smooth.
  • Add the espresso powder and boiling water to the measuring cup, no need to wash it, whisk until incorporated and pour the mixture into the mixing bowl, whisking a final time.
  • Pour the batter over the pears in the prepared pan and bake for 25 to 30 minutes, rotating at the halfway point. The cake is ready when a toothpick inserted in the middle comes out with a moist crumb or two.
  • Immediately run a paring knife around the edge of the skillet. Let sit for 5 minutes, then carefully invert the cake onto a serving platter.
  • Let cool until the caramel sets a bit, about 20 minutes, or cool to room temperature. Serve with vanilla ice cream or whipped cream.
  • The cake will keep wrapped in plastic on the counter for up to 3 days, but it is best the day it is made.

Subscribe to My Newsletter

Subscribe to my bi-monthly (extraordinarily newsy) newsletter, chock full of recipes and fascinating personal tidbits.

Invalid email address
I promise not to spam you. You can unsubscribe at any time.

4 replies on “Chocolate Pear Upside Down Cake”

5 stars
Just inverted into a plate.
It looks wonderful!
It been years since I baked a cake and when I saw this recipe knew I had to try it.

Thank you for this lovely recipe!

4 stars
Thank you for the recipe. I liked the topping of pear with caramel! And the cake itself was easy to whip up (appreciated the instagram video). My only disappointment(?) was that the came was made from scratch…but tasted so much like the box mix cake (which is still delicious!) but I’d worry someone would think I cheated 😂. I’d almost half the cake next time to emphasize the pears and caramel more.

love your criticism of this cake!! as making homemade cake taste boxed is always my goal!

Leave a Reply

Your email address will not be published. Required fields are marked *

Recipe Rating