Classic American Pineapple Upside Down Cake is a delicious vanilla cake with a caramelized topping made up of brown sugar, pineapples, and cherries. It’s a beautiful cake that tastes just as good!
When you think of Classic American desserts you might think of apple pie, red velvet cake, chocolate chip cookies or today’s recipe-Pineapple Upside Down Cake! And this homemade version is a family favorite.
Homemade Pineapple Upside Down Cake
This cake is perfect at any time of year, but growing up, this cake was traditionally served when spring/summer would roll around! It’s light and fruity and looks like a work of art.
Although you begin with the pineapple and cherries on the bottom of the pan, they end up on top and decorate the cake beautifully. You can arrange your pineapples in different ways, such as in full circles or half circles, interlocking, side by side, or overlapping.
Then add in Maraschino cherries in the middle of the pineapple rings or where ever there are open spaces and you’ll have yourself a beautiful masterpiece. We love to have it for picnics, BBQs or any summer celebration but it’s also great for holidays.
How to Make Pineapple Upside Down Cake
- Begin by melting butter in a 9″ pie dish and then add in your brown sugar (spreading it out evenly)
- Place pineapple slices and cherries in the bottom of the pan, trying to fill any empty spaces
Begin with the wet ingredients: In the bowl of a stand mixer (or large mixing bowl with a hand mixer) beat butter and sugar, until light and fluffy
Add eggs, mixing well after each addition. Add vanilla extract and beat for 15 seconds on medium speed.
In a separate bowl combine the dry ingredients; flour, baking powder, and salt.
Alternate adding the flour, milk, and pineapple juice to the wet ingredients. Mix until combined.
Combine the cake with the pineapple
Pour the batter over the pineapple and cherry topping into an even layer.
Place in the oven and bake for 30 minutes.
At the 30 minute mark, loosely cover the cake with foil and continue to bake an additional 15-20 minutes, or until a toothpick inserted in the center comes out clean.
Remove from the oven and allow to cool to for 15 minutes before inverting onto a plate or cake stand.
Let the cake cool for an additional 20 minutes before slicing and serving. I recommend serving it with a big scoop of vanilla ice cream!
- Shortcut: you can use a vanilla/white boxed cake mix instead of a homemade cake
- How to make sure it doesn’t stick: You can use a cake pan lined with greased parchment paper but my best advice is to make sure you wait to let the cake cool and run a knife gently around the edge of the pan before flipping it onto the cooling rack.
- How to avoid soggy cake: If your pineapple slices aren’t totally dry you risk the liquid seeping out into the cake and getting it all soggy and too soft. Pat them dry with a paper towel before placing them in your cake pan.
Variations + Additions
Cupcakes: You can make these into cupcake form but you need to make a few adjustments
- Inverted cupcakes won’t stand very well since cupcakes tend to dome when baked. Consider leveling the top of the cupcakes before inverting them.
- Another tip is to use crushed pineapple rather than pineapple rings because it fits better in the tin. Just make sure to let the pineapple sit in a strainer for 15-20 minutes. Press it with a wooden spoon to release all the extra juices.
- The most common pan size seems to either be a 9×9 square, or a 9-inch pie dish. You can use different pan sizes you will just have to watch the bake times.
Storing Tips + Tricks
My recommendation is that you serve this cake on the same day that you make it! Keep it in the refrigerator until you are ready to serve it, to help it retain its freshness!
You can store any leftovers in the refrigerator for up to 3 days in an airtight container, plastic wrap or cake cover.
To freeze this cake let the cake cool completely and then leave in the fridge overnight before wrapping it tightly in plastic wrap and placing it in the freezer. Keep it for up to 3 months. Let it thaw in the fridge.
This cake is delicious, but don’t forget the side of vanilla ice cream to go with it!!
Other pineapple recipes:
For more cake recipes, check out:
Pineapple Upside Down Cake Recipe
For the topping:
- 1/4 cup (1/2 stick) unsalted butter - melted
- 1/2 cup brown sugar - packed
- 7 sliced pineapple rings - dabbed dry, reserve juice for later
- 12-15 maraschino cherries - dabbed dry
For the cake:
- 1/2 cup (1 stick) unsalted butter - room temperature
- 3/4 cup granulated sugar
- 2 eggs
- 1 1/2 tsp vanilla extract
- 1/4 tsp almond extract
- 1 1/2 cup all-purpose flour
- 1 1/2 tsp baking powder
- 1/4 tsp kosher sea salt
- 1/4 cup milk
- 1/4 cup pineapple juice - reserved from can of pineapple rings
- Preheat oven to 350 degrees.
- Pour melted butter into 9" pie dish or tall metal cake pan. Using your fingers or a spatula, spread the butter onto the sides of the dish/pan.
- Sprinkle the brown sugar over the butter mixture into an even layer. Place the pineapple slices over the bottom of the pan. Cut the leftover slices in quarters to fill in any of the large gaps near the edges of the dish/pan.
- Place cherries in center of pineapple rings and in the remaining empty spaces.
- To make the cake, in the bowl of a stand mixer or in a large mixing bowl with a hand mixer, beat butter and sugar for 2 minutes on medium speed, or until light and fluffy. Add eggs, mixing well after each addition. Add vanilla extract and beat for 15 seconds on medium speed.
- In a separate mixing bowl, whisk together the flour, baking powder, and salt.
- Alternate adding the flour, milk, and pineapple juice to the wet ingredients. Mix until combined. Pour the batter over the pineapple and cherry topping. Using a spatula, spread the batter into an even layer.
- Place in the oven and bake for 30 minutes. At the 30 minute mark, loosely cover the cake with foil and continue to bake an additional 15-20 minutes, or until a toothpick inserted in the center comes out clean.
- Remove from the oven and allow to cool to for 15 minutes before inverting onto a plate or cake stand. Let the cake cool for an additional 20 minutes before slicing and serving. This cake is best eaten on the day it is made, served with a big scoop of vanilla ice cream.