Classic Pineapple Upside-Down Cake with Cherries

Few desserts evoke nostalgia quite like a Pineapple Upside-Down Cake. Its golden caramelized top, adorned with sweet pineapple rings and maraschino cherries, is a feast for the eyes and the palate. This Classic Pineapple Upside-Down Cake with Cherries is a recipe that has stood the test of time—perfect for holidays, birthdays, or any occasion where a classic, comforting dessert is called for.

With its moist, tender crumb and naturally sweet fruit topping, this cake is as visually stunning as it is delicious. Whether you’re baking it for a family gathering, an office potluck, or simply to enjoy with afternoon tea, this cake delivers the perfect combination of sweetness, tang, and richness that makes every bite memorable.

Why You’ll Love This Pineapple Upside-Down Cake

• Timeless dessert: A nostalgic treat that has been cherished for generations.
• Beautiful presentation: Pineapple rings and cherries create a colorful, elegant topping with minimal effort.
• Moist and tender crumb: Sour cream and pineapple juice in the batter keep the cake soft and flavorful.
• Simple ingredients: Pantry staples combine with canned pineapple to create a dessert that’s easy to make yet impressive.
• Customizable: Add extra pineapple, nuts, or spices to make it your own.
• Perfect for all occasions: From family dinners to holiday celebrations, this cake is always a hit.

Ingredients Breakdown

Topping

• 20 ounces canned pineapple slices in juice (not syrup)
• 12 to 18 maraschino cherries
• 4 tablespoons unsalted butter, melted
• 1/2 cup brown sugar

Cake

• 1 1/2 cups all-purpose flour
• 1 teaspoon baking powder
• 1/4 teaspoon baking soda (or use 1 extra teaspoon baking powder)
• 1/4 teaspoon salt
• 1/3 cup milk (whole or low-fat)
• 1/4 cup reserved pineapple juice (from the can)
• 1/4 cup full-fat sour cream (or plain yogurt)
• 1 teaspoon vanilla extract
• 1 stick (1/2 cup) unsalted butter, softened
• 3/4 cup white sugar
• 2 large eggs, at room temperature
• Any extra pineapple, chopped (optional)

Yield: 10 servings
Total Time: 1 hour 5 minutes

Tools & Equipment Needed

• 9-inch round cake pan (not springform)
• Small brush for spreading butter
• Mixing bowls
• Electric hand mixer or stand mixer
• Measuring cups and spoons
• Whisk and spatula
• Toothpick for testing doneness
• Cooling rack
• Serving plate for flipping the cake

Step-by-Step Instructions

1. Preheat Oven and Prepare Pan

1. Set your oven to 350°F (175°C).
2. Dry the pineapple slices and cherries using paper towels to remove excess juice.
3. Pour 4 tablespoons melted butter into a 9-inch round cake pan. Use a brush to spread the butter evenly across the base and slightly up the sides.
4. Sprinkle 1/2 cup brown sugar evenly over the butter to create the caramel layer.

2. Arrange the Fruit

1. Place one pineapple ring in the center of the pan. Arrange the remaining rings or halved slices around it.
2. Add maraschino cherries to the center of the pineapple rings or scatter them as desired.
3. Press the fruit gently so it makes direct contact with the buttered, sugared base.

3. Mix the Cake Batter

1. In a medium bowl, whisk together 1 1/2 cups flour, 1 teaspoon baking powder, 1/4 teaspoon baking soda, and 1/4 teaspoon salt.
2. In a separate bowl, mix 1/3 cup milk, 1/4 cup reserved pineapple juice, 1/4 cup sour cream, and 1 teaspoon vanilla extract.
3. In a third bowl, beat the 1/2 cup softened butter with 3/4 cup white sugar using a hand mixer on medium-high for 2 minutes, until light and fluffy.
4. Add the eggs one at a time, beating for 20 seconds after each addition.

4. Combine Ingredients

1. Add one-third of the dry ingredients to the butter mixture, stirring with a spatula.
2. Mix in half of the wet ingredients.
3. Repeat, alternating between dry and wet ingredients until fully combined.
4. Gently fold in any leftover chopped pineapple.

5. Assemble and Bake

1. Pour the batter over the fruit in the pan and smooth the surface with a spatula.
2. Bake uncovered for 30 minutes.
3. Cover loosely with foil and bake for an additional 15 minutes, or until a toothpick inserted into the center comes out clean.

6. Cool and Flip

1. Let the cake cool in the pan for 20 minutes.
2. Run a butter knife along the edge to loosen the cake.
3. Place a serving plate over the pan and flip the cake upside-down. Gently tap or shake the pan to release it.
4. Allow the cake to cool completely before slicing.

Tips & Variations

• Extra caramel flavor: Sprinkle a few extra tablespoons of brown sugar on top of the fruit before adding the batter.
• Add spices: Cinnamon, nutmeg, or ginger can be mixed into the batter for a warmer flavor profile.
• Fruit variations: Substitute or add peaches, mango, or other canned fruits for variety.
• Nuts for crunch: Sprinkle chopped pecans or walnuts over the brown sugar layer before adding the fruit.
• Mini cakes: Make individual portions in muffin tins for a fun variation.

Flavor Profile

This cake offers a perfect balance of sweetness and tang. The caramelized brown sugar and butter complement the tart pineapple and sweet cherries. The tender, moist cake base adds richness and structure, while the golden caramel topping creates a beautiful glossy finish. Each bite delivers a mix of textures: soft cake, juicy fruit, and slightly sticky caramel.

Serving Suggestions

• Serve warm for maximum flavor and caramel aroma.
• Pair with whipped cream or vanilla ice cream for added decadence.
• Garnish with extra cherries or pineapple chunks for a festive presentation.

Nutritional Overview (Per Serving)

Nutrient	Amount
Calories	290 kcal
Protein	3 g
Carbohydrates	45 g
Fat	11 g
Fiber	2 g
Sugar	32 g

Dietary notes: Contains dairy; can be adapted with vegan butter and yogurt alternatives.

Make-Ahead & Storage Tips

• Prepare ahead: Assemble the cake up to 24 hours in advance. Store covered in the fridge. Bake just before serving for a fresh dessert.
• Storage: Keep at room temperature for 1–2 days; refrigerate for up to 4 days.
• Reheating: Warm slices in the microwave or oven to revive the caramelized topping.
• Freezing: Wrap cooled cake tightly in plastic wrap and foil. Freeze for up to 2 months. Thaw overnight in the fridge before serving.

FAQs

Q: Can I use fresh pineapple instead of canned?
A: Yes, use ripe, peeled pineapple slices. Pat dry before arranging in the pan.

Q: Do I need a non-stick pan?
A: A regular 9-inch round pan works well if it’s well buttered. Avoid springform pans as the caramel may leak.

Q: Can I add more cherries?
A: Absolutely. Scatter as desired for visual appeal and flavor.

Q: Why does the cake sometimes stick when flipping?
A: Ensure the pan edges are loosened with a knife and use a plate larger than the pan. Tapping gently helps release it.

Q: Can this be made gluten-free?
A: Substitute flour with a 1:1 gluten-free blend. Baking times may need slight adjustment.

Cooking Timeline (At a Glance)

Stage	Time
Prep pan & fruit	10 min
Mix batter	10 min
Assemble & bake	45 min
Cool & flip	20 min

Pro Baking Tips

• Always dry the pineapple slices and cherries before arranging to prevent excess liquid in the caramel.
• Beat butter and sugar until fluffy to create a tender cake crumb.
• Alternate dry and wet ingredients to avoid overmixing and a dense cake.
• Allow the cake to cool slightly before flipping to avoid fruit sliding or breaking.

Ingredient Spotlight

Pineapple: Provides natural sweetness, moisture, and flavor. Canned pineapple is convenient and consistent in texture.

Cherries: Maraschino cherries add color, sweetness, and visual appeal. They complement the tart pineapple perfectly.

Brown sugar: Creates the caramel layer that defines the classic upside-down cake, giving it that glossy, rich finish.

Storage & Freezing Guide

• Room temperature: Store covered for up to 2 days.
• Refrigeration: Keep airtight for up to 4 days.
• Freezing: Wrap cooled cake in foil and plastic wrap. Freeze for up to 2 months. Thaw in fridge overnight.
• Reheating: Warm slices in a 350°F oven for 5–10 minutes or in the microwave.

Expanded Conclusion

This Classic Pineapple Upside-Down Cake with Cherries is more than a dessert—it’s a slice of nostalgia. Its golden caramelized topping, tender cake, and juicy fruit make it a timeless treat for all occasions. Whether you bake it for a holiday feast, family gathering, or casual afternoon treat, it’s sure to impress and delight.

With simple ingredients and an easy-to-follow process, this cake proves that classic desserts never go out of style. Serve it warm, share it generously, and savor the memories that this beloved recipe brings to the table.

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