Vintage 1930’s Pineapple Upside‑Down Cake (Old‑Fashioned, Easy & Delicious)

 

 

Step back in time with this Vintage 1930’s Pineapple Upside‑Down Cake, a true classic from the era when home bakers relied on simple pantry staples and a whole lot of heart. This old‑fashioned dessert is everything we love about retro baking — buttery caramelized pineapple, jewel‑bright cherries, and a tender, moist from scratch cake that turns out perfectly every time. It’s the kind of recipe that has been passed down through generations, cherished for its reliability, beauty, and irresistible flavor.

Whether you’re craving a taste of nostalgia, looking for a dessert that always impresses, or simply love the charm of vintage recipes, this Pineapple Upside‑Down Cake delivers. It’s easy to make, wonderfully comforting, and brings that timeless 1930s magic right into your modern kitchen. One slice and you’ll understand why this classic has never gone out of style.

Eileen had been wanting me to make her a Pineapple Upside Down Cake for weeks now. She said she had not had one since she had been living at home eons ago. I finally got around to baking her one today and she is one very happy camper!

As you know I really love vintage recipes. I feel they still have a lot of value in today's world, and I am a sentimental sort of person, so vintage recipes really speak to the heart of me. They have been pleasing individual and families for many, many years. What could ever be wrong about that!

I got this recipe from the Better Homes & Gardens All-time Favorites Cookbook. It is chocker-block full of lovely vintage recipes that have withstood the test of time. Today's cake recipe is from the 1930's and is one that our grandmothers and great grandmothers might have baked.

I loved that it did not use either a cake mix, nor any shortening. All butter. Simple ingredients. Not a preservative in sight. Pure butter, organic sugar (My choice), farm fresh eggs and milk. A quality unbleached flour. (Again, my choice.)

I did use tinned pineapple as that is all I had, and maraschino cherries are maraschino cherries, the manufacture of which can be a bit spurious, but there are not a lot of them. They do make for a very pretty cake.

Eileen was in Upside Down Cake Heaven. This was a moist and delicious cake with a beautiful crumb and lovely lush and sweet fruity topping. We enjoyed slices of this while it was still warm with some whippy cream.  It was delicious!

 

INGREDIENTS NEEDED

TO MAKE

VINTAGE 1930'S PINEAPPLE UPSIDE DOWN CAKE  

For the most part, simple pantry ingredients.

For the topping/base:

• 2 TBS butter
• 1/3 cup (56.7g) soft light brown sugar, packed
• 1 TBS pineapple juice
• 5 pineapple rings
• 5 maraschino cherries

For the cake batter:

• 1 1/3 cups (160g) plain all-purpose flour
• 2/3 cup (133g) granulated sugar
• 2 tsp baking powder
• 2/3 cup (180ml) milk
• 1/4 cup (57g) butter, softened
• 1 large egg
• 1 tsp vanilla extract

NOTES ON INGREDIENTS NEEDED

TO MAKE

VINTAGE 1930'S PINEAPPLE UPSIDE DOWN CAKE

• Make sure all of your ingredients are at room temperature.  Take any butter, milk and eggs out from the refrigerator at least half an hour prior to beginning.
• Measure everything exactly as per the recipe requirements. Baking is an exact science.
• You can freeze any pineapple rings that don't get used in an airtight container for another time.
• Pat your fruit dry with paper towels before using.
• In the U.K. I would use caster sugar and not granulated sugar for the cake.
• Pack your brown sugar tightly into the measuring cup.
• I used whole milk as that is all I keep in the house.
• I used salted butter and pure vanilla extract.

 

HOW TO MAKE

VINTAGE 1930'S PINEAPPLE UPSIDE DOWN CAKE 

This is really a very simple cake to make. Just read through and follow the instructions carefully.

1. Preheat the oven to 350*F/180*C/ gas mark 4. Place the 2 TBS butter into a 9-inch round, 2-inches deep, baking tin. Pop into the oven to melt while the oven preheats. Once the butter has melted, remove from the oven. (Don't let it brown, remove it from the oven as soon as it has melted.)
2. Add the brown sugar and pineapple juice to the melted butter. Whisk together to combine well and spread out to cover the bottom of the pan. (I used a small metal teaspoon to do this. It worked great. Make sure you cover the entire bottom.)
3. Cut four of the pineapple rings/slices in half and arrange around the outside of the pan. Put one full ring in the center. (Normally I have kept the slices whole, but was intrigued that in this old recipe they are cut in half. This made for a pretty presentation, and made a little bit of pineapple go a long way.)
4. Cut four of the maraschino cherries in half and place in the center of each half ring of pineapple and place the fifth cherry in the middle of the center full ring of pineapple. (I did not cut the cherry in the middle in half. I think you could probably use whole cherries all around without any problems.)
5. Whisk the flour, sugar and baking powder together in a bowl to combine well. Add the softened butter, milk, egg and vanilla. Beat on low until combined and then beat on medium for one minute until smooth. (Whisking the flour together first evenly distributes the baking powder in the cake batter.)
6. Spoon the batter carefully over the pineapple in the pan to cover, smoothing it out. (Try not to dislodge any of the pineapple or cherries.)
7. Bake in the preheated oven for 35 to 40 minutes, or until a toothpick inserted in the center comes out clean.
8. Leave to cool in the pan on a wire rack for 5 minutes. (This is important.)
9. Loosen sides and carefully invert onto a plate. (I did not have the problem that I have had with other cakes and there being too much topping. This amount was just right. I did manage to dislodge the pineapple and topping a bit, but it was nothing that a good spoon and a tiny bit of effort couldn't fix.)
10. Serve warm and cut into wedges with or without whipped cream or vanilla ice cream. (We enjoyed it with squirty whipped cream.)

 

HINTS AND TIPS FOR BEST RESULTS

WHEN MAKING

VINTAGE 1930'S PINEAPPLE UPSIDE DOWN CAKE 

• Read through the recipe completely before beginning to help familiarize yourself with any ingredients equipment, etc. that you might need to make this cake.
• Assemble all of the ingredients before you begin. This can help to prevent you from leaving anything out by accident.
• Have all of your ingredients at room temperature for the best results.
• Dry the fruit before using. Pat dry using some paper kitchen towels.
• Don't overbeat the cake batter. This will toughen the batter. You need only mix things together until smooth and evenly combined. 
• Use the correct size of pan for the recipe. This is meant to be baked in a 9-inch round cake tin. 2-inches deep.
• Leave the cake to cool in the pan for at least five minutes before loosening it around the edges and tipping it out onto a plate.

 

FREQUENTLY ASKED QUESTIONS 

CAN THIS CAKE BE MADE AHEAD OF TIME?

You could certainly make it up to a few hours ahead of time, but this is a cake that is really best served on the day.

HOW DO I STORE ANY LEFTOVERS?

Leftovers should be refrigerated due to the fresh nature of the fruit. You may also freeze the cake for up to three months. Wrap in plastic cling film and then a layer of aluminum foil. Label, date and freeze.

CAN I USE FRESH PINEAPPLE TO MAKE THIS CAKE?

Yes, you can use fresh pineapple.

DO I NEED TO USE MARASCHINO CHERRIES?

Not at all, although they do make for a very pretty presentation. In their place you can use glace cherries,  or toasted walnuts or pecans.

IS THERE ANY OTHER SIZE OF PAN I CAN USE?

You can use a 9-inch square baking tin if that is all you have. Bake times would remain the same.

 

A FEW OTHER DESSERT CAKES FOR YOU TO ENJOY

Cake for dessert?  Count me in!!! Here are a few other versions on the same theme that you might also enjoy!

PEAR & MAPLE UPSIDE DOWN CAKE - This cake is a cozy twist on a nostalgic classic — a tender, maple‑kissed sponge baked over a glistening layer of buttery brown sugar, soft pears, and toasted pecans. The magic begins with tinned pear halves nestled into a maple‑sweetened caramel base, each one crowned with a pecan for a touch of rustic elegance. The batter itself is beautifully simple and old‑fashioned, inspired by the beloved Purity Cookbook, enriched with maple flavoring for a deeper, warmer sweetness that pairs perfectly with the fruit. Once flipped, the cake reveals its stunning mosaic of pears and pecans — golden, sticky, and utterly inviting. Served warm with a scoop of ice cream or a cloud of whipped cream, it’s the kind of dessert that feels both comforting and special.

RHUBARB UPSIDE DOWN CAKE - This cake is one of those bakes that feels like pure kitchen alchemy — simple ingredients transforming into something far more beautiful and delicious than the sum of their parts. Early forced rhubarb, with its brilliant pink color and delicate flavor, becomes the star here, melting into a glossy, sweet‑tart layer as it bakes beneath a soft, tender sponge. Its vivid hue and gentle tang make it the perfect ingredient to showcase in a cake meant to brighten the tail end of winter and welcome spring.  As the cake bakes, the fruit and sugar topping softens into a luscious, almost jammy crown while the batter — light, fluffy, and beautifully old‑fashioned — rises around it. The result is a dessert that unmolds into a stunning mosaic of pink, glossy rhubarb, each slice offering that irresistible contrast of sweet sponge and tart fruit. 

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Yield: 8 servings

Author: Marie Rayner

1930's Pineapple Upside Down Cake

Prep time: 14 MinCook time: 40 MinTotal time: 54 Min

Pineapple, brown sugar, butter and pineapple juices bubble up to form a delicious topping in this quick and easy to make vintage recipe.

Ingredients

For the topping/base:

• 2 TBS butter
• 1/3 cup (56.7g) soft light brown sugar, packed
• 1 TBS pineapple juice
• 5 pineapple rings
• 5 maraschino cherries

For the cake batter:

• 1 1/3 cups (160g) plain all-purpose flour
• 2/3 cup (133g) granulated sugar
• 2 tsp baking powder
• 2/3 cup (180ml) milk
• 1/4 cup (57g) butter, softened
• 1 large egg
• 1 tsp vanilla extract

Instructions

1. Preheat the oven to 350*F/180*C/ gas mark 4. Place the 2 TBS butter into a 9-inch round, 2-inches deep, baking tin. Pop into the oven to melt while the oven preheats. Once the butter has melted, remove from the oven.
2. Add the brown sugar and pineapple juice to the melted butter. Whisk together to combine well and spread out to cover the bottom of the pan.
3. Cut four of the pineapple rings/slices in half and arrange around the outside of the pan. Put one full ring in the center.
4. Cut four of the maraschino cherries in half and place in the center of each half ring of pineapple and place the fifth cherry in the middle of the center full ring of pineapple.
5. Whisk the flour, sugar and baking powder together in a bowl to combine well. Add the softened butter, milk, egg and vanilla. Beat on low until combined and then beat on medium for one minute until smooth.
6. Spoon the batter carefully over the pineapple in the pan to cover, smoothing it out.
7. Bake in the preheated oven for 35 to 40 minutes, or until a toothpick inserted in the center comes out clean.
8. Leave to cool in the pan on a wire rack for 5 minutes.
9. Loosen sides and carefully invert onto a plate.
10. Serve warm and cut into wedges with or without whipped cream or vanilla ice cream.

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