Why You’ll Love This Recipe
This cake brings together the perfect balance of sweetness and tanginess. The caramelized pineapple on top creates a beautiful, glossy finish, while the soft, rich cake beneath it is simply delicious. It’s easy to make, visually appealing, and a hit at any gathering.
Ingredients
- 1/4 cup unsalted butter, melted
- 3/4 cup packed brown sugar
- 1 can (20 oz) sliced pineapple, drained (reserve juice)
- 9 maraschino cherries
- 1 1/2 cups all-purpose flour
- 1 cup granulated sugar
- 1/2 cup unsalted butter, softened
- 2 large eggs
- 1 teaspoon vanilla extract
- 1/2 cup milk (or reserved pineapple juice)
- 2 teaspoons baking powder
- 1/4 teaspoon salt
(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)
Directions
- Preheat your oven to 350°F (175°C). Grease a 9-inch round cake pan.
- Pour the melted butter into the bottom of the prepared pan, then sprinkle the brown sugar evenly over the butter.
- Arrange the pineapple slices on top of the brown sugar, and place a cherry in the center of each pineapple ring.
- In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. Add the eggs, one at a time, beating well after each addition. Stir in the vanilla extract.
- In another bowl, whisk together the flour, baking powder, and salt. Add the dry ingredients to the wet ingredients alternately with the milk (or reserved pineapple juice), beginning and ending with the dry ingredients. Mix until just combined.
- Pour the batter over the pineapple slices in the pan and smooth the top with a spatula.
- Bake in the preheated oven for 40-45 minutes, or until a toothpick inserted into the center comes out clean.
- Let the cake cool for 5 minutes, then run a knife around the edges. Invert the cake onto a plate and carefully remove the pan.
- Allow the cake to cool completely before serving.
Servings and Timing
This recipe serves 8.
- Prep time: 15 minutes
- Cook time: 40-45 minutes
- Total time: 1 hour
Variations
- Use other fruits: Try using peaches or cherries instead of pineapple for a twist on the classic.
- Add spices: A dash of cinnamon or nutmeg can add a warm, cozy flavor to the cake.
- Vegan version: Use dairy-free butter and non-dairy milk for a vegan-friendly version of this cake.
Storage/Reheating
Store leftover cake in an airtight container at room temperature for up to 3 days. To keep the cake fresh for longer, refrigerate it for up to 1 week. You can reheat slices in the microwave for 10-15 seconds.
FAQs
Can I use fresh pineapple instead of canned?
Yes, fresh pineapple works perfectly. Just slice it into rings and caramelize them before adding to the cake.
Can I make this cake ahead of time?
Yes, this cake can be made a day ahead. Just store it in an airtight container and enjoy it the next day.
Can I freeze this cake?
Yes, you can freeze this cake for up to 2 months. Make sure it’s wrapped tightly in plastic wrap and foil before freezing.
What’s the best way to serve this cake?
This cake is delicious on its own or served with whipped cream or vanilla ice cream for extra indulgence.
Can I use a different size pan?
If you use a different size pan, adjust the cooking time accordingly. A smaller pan will require a longer baking time, while a larger pan will cook faster.
Can I add coconut to the cake?
Yes, shredded coconut can be sprinkled on top of the pineapple before baking for an extra tropical touch.
What can I use instead of maraschino cherries?
You can use fresh cherries or even candied cherries as a substitute.
How do I prevent the cake from sticking to the pan?
Grease the pan well and line it with parchment paper to ensure the cake comes out easily.
Can I make this recipe gluten-free?
Yes, you can substitute the all-purpose flour with a gluten-free flour blend to make it gluten-free.
How do I know when the cake is done?
When the cake is done, it will be golden brown on top, and a toothpick inserted into the center should come out clean.
Conclusion
This Old Fashioned Pineapple Upside-Down Cake is a delicious and easy-to-make treat that will remind you of simpler times. The caramelized pineapple and cherries on top, combined with the soft cake, create a flavorful and comforting dessert that’s perfect for any occasion. Enjoy!

Old Fashioned Pineapple Upside-Down Cake
- Prep Time: 15 minutes
- Cook Time: 40–45 minutes
- Total Time: 1 hour
- Yield: 8 servings
- Category: Dessert, Cake
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
This Old Fashioned Pineapple Upside-Down Cake is a classic American dessert featuring a rich, buttery cake topped with sweet caramelized pineapple rings and vibrant maraschino cherries. It’s a retro recipe that’s as beautiful as it is delicious, with a golden glaze and a perfectly tender crumb. This easy, crowd-pleasing treat is ideal for holidays, potlucks, or anytime you’re craving a nostalgic homemade dessert.
Ingredients
- 1/4 cup unsalted butter, melted
- 3/4 cup packed brown sugar
- 1 can (20 oz) sliced pineapple, drained (reserve juice)
- 9 maraschino cherries
- 1 1/2 cups all-purpose flour
- 1 cup granulated sugar
- 1/2 cup unsalted butter, softened
- 2 large eggs
- 1 teaspoon vanilla extract
- 1/2 cup milk (or reserved pineapple juice)
- 2 teaspoons baking powder
- 1/4 teaspoon salt
Instructions
- Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan.
- Pour melted butter into the pan and evenly sprinkle brown sugar over it.
- Arrange pineapple slices on top of the sugar and place a cherry in each ring’s center.
- In a large bowl, cream softened butter and granulated sugar until light and fluffy.
- Beat in eggs one at a time, then stir in vanilla extract.
- In another bowl, whisk flour, baking powder, and salt.
- Alternate adding the dry mixture and milk (or pineapple juice) into the creamed mixture, starting and ending with the dry ingredients. Mix just until combined.
- Gently pour batter over the arranged fruit and smooth the top.
- Bake for 40–45 minutes, or until a toothpick comes out clean.
- Cool for 5 minutes, run a knife along the edges, then invert the cake onto a serving plate. Let it cool before slicing.
Notes
- Use fresh pineapple slices for a more natural taste.
- Add cinnamon or nutmeg for extra warmth.
- Substitute dairy-free butter and milk for a vegan-friendly version.
- Sprinkle shredded coconut for a tropical twist.
- Store leftovers at room temperature for 3 days or refrigerate for up to 1 week. Freeze for up to 2 months.