Pineapple upside down cake is a classic buttery cake, baked into a layer of fresh pineapple, sweet cherries and pecans in a brown sugar rum sauce.
Pineapple Upside Down Cake
Upside down cakes, with pineapple upside down cake being the most popular, first appeared in American cookbooks in the early 20th century but have presumably been around a lot longer. Upside down cakes are aptly name so, since the fruit layer is actually baked in the bottom of the pan. After baking, the cake is flipped upside down with the fruit then becoming the topping.
Pineapple upside down cakes took over as the most popular version of the upside down cake after the Dole pineapple company sponsored a baking contest in 1925 to use their canned pineapple. After there were over 2,500 submissions for pineapple upside down cake, as they say, the rest is history!
About this Recipe
This pineapple upside down cake is a classic light and buttery cake, baked into a layer of fresh pineapple, sweet cherries and pecans in a brown sugar rum sauce. Read below about journey to perfect this old-fashioned dessert that eventually became one of my award winning cakes!
Vintage cookbooks are filled with pineapple upside down cakes and I’ve had this cake on my “to do” list for quite some time. In my quest to find which pineapple upside down cake from my vintage recipe collection was the best, I ended up testing so many recipes! Ultimately in the end, I adapted this recipe using elements from several different recipes, one recipe dating to the 1930’s.
I found using fresh pineapple gave the best pineapple flavor and allowed the pineapple to candy and almost caramelize while baking. I also settled on a cake recipe that was buttery, yet light and complemented the brown sugar rum sauce. I also tested this cake using fresh cherries but settled on using maraschino cherries, since I found using fresh cherries in addition to the fresh pineapple caused the cake to become almost soggy. Adding nuts to the brown sugar rum sauce also provided some texture to this cake, but you can use any type of nut or omit them all together.
Pineapple upside down cake may not be the prettiest cake you will ever make, but the classic flavors really blend well together. Serve it for brunch, dessert (or any time of day!) Read more below on how to make this delicious cake.
How to Make This Recipe
While this cake may take some extra time to prep, once all ingredients have been prepped it really comes together quickly.
Ingredients
- Unsalted butter
- Light brown sugar
- Fresh pineapple
- Maraschino cherries
- Chopped pecans
- Dark rum (optional)
- All-purpose flour
- Baking soda
- Salt
- Granulated sugar
- Eggs
- Vanilla extract
- Milk
To begin, line your cake pan with parchment paper first. This helps the topping stay in place when you flip the cake. You will need to prep the pineapple topping first. Chop the fresh pineapple into triangles that are even in both thickness and size. Then, butter and brown sugar are melted together and if using, dark rum is added. This is spread into the bottom of the lined cake pan and then the chopped pineapple, maraschino cherries and pecans are evenly layered on top.
The batter for the cake comes together quickly by sifting all of the dry ingredients together in a small mixing bowl. The butter and granulated sugar are creamed together until light and then the eggs and vanilla extract are added. The sifted dry ingredients are mixed in alternately with the milk and mixed only until just combined. The batter is then spread on top of the pineapple layer very carefully and baked until a toothpick inserted in the middle of the cake comes out clean. This is an important step you want to take for this recipe, as you do not want to under bake this cake.
After the cake has cooled in the pan for 10-15 minutes, you can run a knife around the edges and flip the a cake onto a serving platter, gently placing any of the pineapple back into place on top of the cake. You can serve this cake warm or at room temperature. See storage tips below.
Tips for Pineapple Upside Down Cake
- You can substitute canned pineapple for the fresh pineapple, although the pineapple flavor will not be as strong
- Pineapple upside down cake is best eaten the day it is made; serve warm or room temperature
- If you have leftovers, keep this cake covered and refrigerate up to 24 hours. After 24 hours, the cake will become soggy.
- Pay attention to your pan size; you need a large enough pan to bake the cake layer evenly, which will prevent the cake from under baking. I used a tall 9 inch round cake pan, you can also substitute a 9 inch springform pan, too.
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Pineapple Upside Down Cake
Equipment
- 9" round cake pan OR 9" springform cake pan
- parchment paper
- mixer and mixing bowls of various sizes
Ingredients
Topping:
- 1/3 cup unsalted butter
- 2/3 cup light brown sugar packed
- 1 cup fresh pineapple chunks cut into small triangles about ¼” thick
- ¼ cup maraschino cherries
- ¼ cup pecans roughly chopped
- 1 Tablespoon dark rum (optional)
Cake:
- 1 ½ cups all-purpose flour
- 2 teaspoons baking powder
- ¼ teaspoon salt
- ½ cup unsalted butter, softened
- ¾ cup granulated sugar
- 2 large eggs, room temperature
- 1 teaspoon vanilla extract
- ½ cup milk
Instructions
For the topping:
- In a microwave safe bowl, melt the 1/3 cup unsalted butter
- Add the 2/3 cup light brown sugar and 1 Tablespoon dark rum (if using) and mix well; spread into the bottom of a greased 9” round cake pan.
- Arrange the 1 cup fresh pineapple chunks, ¼ cup maraschino cherries and ¼ cup pecans evenly over the brown sugar mixture.
For the cake:
- Preheat the oven to 350° F. Line a 9" round cake pan or 9" springform pan with parchment paper. Grease cake pan liberally.
- In a medium sized mixing bowl, sift the 1 ½ cups all-purpose flour, 2 teaspoons baking powder and ¼ teaspoon salt
- In the bowl of a stand mixer or using an electric mixer and a large mixing bowl, cream the ½ cup unsalted butter, and ¾ cup granulated sugar until light, about two minutes.
- Add in the 2 large eggs,, one at a time, followed by the 1 teaspoon vanilla extract
- Add in half of the dry ingredients, mix only until just combined. Add in the ½ cup milk, followed by the remaining dry ingredients, again only mixing until just combined.
- Spread the batter into the cake pan over the brown sugar and pineapple mixture. Bake in a preheated oven at 350° F for 35-40 minutes, or until a toothpick inserted into the center of the cake comes out clean.
- Cool the cake pan on a wire rack 10-15 minutes and then invert on to a serving platter (or release sides if using a springform pan and then invert). Gently place any of the pineapple topping back into place that became displaced after inverting. Serve warm or at room temperature.
Notes
- You can substitute canned pineapple for the fresh pineapple, although the pineapple flavor will not be as strong
- Pineapple upside down cake is best eaten the day it is made; serve warm or room temperature
- If you have leftovers, keep this cake covered and refrigerate up to 24 hours. After 24 hours, the cake will become soggy.
- Pay attention to your pan size; you need a large enough pan to bake the cake layer evenly, which will prevent the cake from under baking.
- Makes 12 large slices or 16 smaller slices.