Indulge in a timeless dessert with a moist, buttery cake crowned by caramelized pineapple rings and brilliant maraschino cherries. This classic delight fuses rich flavors from a luscious brown sugar base and tender cake. Enjoy an irresistible treat that offers a perfect balance between sweet, tangy, and vibrant fruit accents.

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I’ve always been drawn to the nostalgia of retro desserts and this Pineapple Upside cake is one of my favorites. It’s a classic recipe that balances rich, buttery flavors with the tang of caramelized pineapple and sweet cherries.

I start with the topping by combining 1/2 cup unsalted butter, melted with 3/4 cup packed light brown sugar. I then carefully layer 7 drained pineapple rings and add 10 maraschino cherries.

For the cake batter, I mix 1 1/2 cups all-purpose flour with 1 cup granulated sugar, 2 teaspoons baking powder and 1/2 teaspoon salt, then blend in 2 large eggs, 3/4 cup milk, 1/3 cup vegetable oil and 1 teaspoon vanilla extract. Despite being a dessert high in sugar and fats, this pineapple cake gives a satisfying balance of nutrients.

It reminds me why Pineapple Upside Down cake always holds a special place in classic desserts.

Why I Like this Recipe

I really love this recipe because it’s super easy to make and always turns out delicious. I like how the melted butter and brown sugar mix together with the pineapple rings and cherries to make a caramel-y, sweet topping. I also appreciate that the cake stays moist and light when you dont overmix the batter, which means i don’t have to worry about it being too dense. Lastly, the whole process reminded me of those family gatherings at home, and that makes every bite extra special.

Ingredients

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Unsalted Butter: adds a rich creamy taste and essential fat, boosting flavor and moist texture everywhere.
Light Brown Sugar: provides deep caramel sweetness and moisture, balancing the dessert perfectly.
Pineapple Rings: deliver tangy, juicy flavor along with vitamin C, brightening the overall taste.
Maraschino Cherries: bring a burst of sweet tartness that make the dessert look super appealing.
Eggs: supply protein and serve as binders, adding a subtle richness to the cake.
Milk: gives a smooth, tender crumb and extra moisture, softening the cake texture.
Vegetable Oil: helps maintain moist cake texture and ensures an even, soft crumb throughout.

Ingredient Quantities

For the topping: 1/2 cup unsalted butter, melted

For the topping: 3/4 cup packed light brown sugar

For the topping: 7 pineapple rings (canned in juice, drained)

For the topping: 10 maraschino cherries, stems removed

For the cake: 1 1/2 cups all-purpose flour

For the cake: 1 cup granulated sugar

For the cake: 2 teaspoons baking powder

For the cake: 1/2 teaspoon salt

For the cake: 2 large eggs, lightly beaten

For the cake: 3/4 cup milk

For the cake: 1/3 cup vegetable oil

For the cake: 1 teaspoon vanilla extract

How to Make this

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1. Preheat your oven to 350°F and grease a 9-inch round cake pan.

2. Pour the melted butter into the pan and sprinkle the brown sugar evenly over it.

3. Arrange the pineapple rings on top of the butter and sugar, then place the maraschino cherries in the center of each ring and in between if needed.

4. In a separate bowl, mix together the flour, granulated sugar, baking powder, and salt.

5. In another bowl, whisk together the eggs, milk, vegetable oil, and vanilla extract until it looks smooth.

6. Slowly stir the wet ingredients into the dry ingredients until just combined; don’t overmix or it will turn out dense.

7. Carefully pour the batter over the pineapple and cherries in the pan, making sure everything stays in place.

8. Bake for about 40 to 45 minutes, or until a toothpick inserted into the center comes out clean.

9. Let the cake cool in the pan for 5 minutes, then run a knife around the edges and invert it onto a serving plate.

10. Enjoy your delicious Pineapple Upside cake warm or at room temperature, and share with friends if you want.

Equipment Needed

1. Preheated oven – make sure it reaches 350°F before you start
2. A 9-inch round cake pan that you’ll grease with butter
3. Two mixing bowls (one for the dry ingredients and one for the wet ingredients)
4. Measuring cups and spoons to get the ingredients right
5. A whisk for beating the wet ingredients until smooth
6. A spatula to stir the batter and to help spread it evenly
7. A knife to run around the edges of the cake pan after baking
8. A toothpick to test if the cake is done
9. A serving plate to invert the cake onto after it cools a bit

FAQ

Can i use fresh pineapple instead of canned?

Yes you can, but fresh pineapple has more water so you might need to reduce the juice or let it drain a bit longer to keep the topping from getting too soggy.

How do i know when the cake is done?

Just poke a toothpick into the center of the cake; if it comes out clean or with just a few crumbs, then its ready to come out of the oven.

Can i swap vegetable oil with another fat?

Sure, you can use melted butter instead, but keep in mind that using butter may change the cake's texture slightly, making it a bit richer.

How should i store leftovers?

Once the cake cools down, cover it with plastic wrap and pop it in the fridge. It should stay fresh for up to 3 days.

Do i have to prepare everything from scratch?

Not really, you can mix the topping ingredients a bit ahead of time then pour your cake batter on top right before baking for an easy setup.

Pineapple Upside Recipe Substitutions and Variations

Unsalted butter: You can use coconut oil or margarine if you dont have butter handy
Light brown sugar: Try using dark brown sugar or even some maple syrup for a richer taste
Granulated sugar: Replace it with honey (use a bit less honey than the sugar called for) for a different sweetness
Vegetable oil: Canola oil or even olive oil works fine if you dont have vegetable oil

Pro Tips

1. Make sure you dont overmix the batter. Stir in the wet into the dry just until you see no flour because overmixing can turn the cake out dense.
2. For a moister cake, you might wanna try substituting a bit of the milk with a little pineapple juice from that can. It adds extra flavor without being too sweet.
3. Spread the butter smooth all over the pan and sprinkle the brown sugar evenly. If you do this well, the topping will caramelize nice and even during bake time.
4. Ovens can vary a lot, so start checking the cake a few minutes before the stated time. This way you can catch any burning edges and adjust the time if needed.

Pineapple Upside Recipe

Recipe by Sam Ecclestone

0.0 from 0 votes

Servings

servings

Calories

350

kcal

Equipment: 1. Preheated oven – make sure it reaches 350°F before you start
2. A 9-inch round cake pan that you’ll grease with butter
3. Two mixing bowls (one for the dry ingredients and one for the wet ingredients)
4. Measuring cups and spoons to get the ingredients right
5. A whisk for beating the wet ingredients until smooth
6. A spatula to stir the batter and to help spread it evenly
7. A knife to run around the edges of the cake pan after baking
8. A toothpick to test if the cake is done
9. A serving plate to invert the cake onto after it cools a bit

Ingredients

For the topping: 1/2 cup unsalted butter, melted
For the topping: 3/4 cup packed light brown sugar
For the topping: 7 pineapple rings (canned in juice, drained)
For the topping: 10 maraschino cherries, stems removed
For the cake: 1 1/2 cups all-purpose flour
For the cake: 1 cup granulated sugar
For the cake: 2 teaspoons baking powder
For the cake: 1/2 teaspoon salt
For the cake: 2 large eggs, lightly beaten
For the cake: 3/4 cup milk
For the cake: 1/3 cup vegetable oil
For the cake: 1 teaspoon vanilla extract

Directions

Preheat your oven to 350°F and grease a 9-inch round cake pan.
Pour the melted butter into the pan and sprinkle the brown sugar evenly over it.
Arrange the pineapple rings on top of the butter and sugar, then place the maraschino cherries in the center of each ring and in between if needed.
In a separate bowl, mix together the flour, granulated sugar, baking powder, and salt.
In another bowl, whisk together the eggs, milk, vegetable oil, and vanilla extract until it looks smooth.
Slowly stir the wet ingredients into the dry ingredients until just combined; don’t overmix or it will turn out dense.
Carefully pour the batter over the pineapple and cherries in the pan, making sure everything stays in place.
Bake for about 40 to 45 minutes, or until a toothpick inserted into the center comes out clean.
Let the cake cool in the pan for 5 minutes, then run a knife around the edges and invert it onto a serving plate.
Enjoy your delicious Pineapple Upside cake warm or at room temperature, and share with friends if you want.

Notes

Below you’ll find my best estimate of this recipe’s nutrition facts. Treat the numbers as a guide rather than a rule—great food should nourish both body and spirit. Figures are approximate, and the website owner assumes no liability for any inaccuracies in this recipe.