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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Easy Yeast‑Free Naan Bread (Soft, Quick & Ready in Minutes)

 

 

 

If you’ve ever wished you could whip up soft, warm naan breads without the time or fuss of working with yeast, you’re going to love this recipe. These Yeast‑Free Naan Breads come together in minutes using simple pantry ingredients, and they cook right on the stovetop — no rising, no kneading, no waiting around. Just mix, roll, and toast until they’re puffed, golden, and irresistibly tender.

They’re perfect for scooping up curries, wrapping around grilled meats, or serving warm with a bit of garlic butter. And because they’re so quick and easy, they’re ideal for busy weeknights or last‑minute meals when you want something homemade but don’t have hours to spare.

If you’ve never made naan before, this is the recipe that will make you wonder why you waited so long. Soft, simple, and ready in a flash — a real kitchen keeper.

 

This delicious recipe for Yeast-Free Naan Breads is one I got from my friend Swedish Marie several years back.  Naan Bread is an East Indian type of bread that is very popular and often served with things like curry's and other Indian foods.  Perfect for mopping up all of their delicious juices and sauces.  (I also like to use them to make quick and easy pizzas.)

I have often found the ready-made Naan breads in the shops quite disappointing. They are often stale and more often than not hard as compared to homemade Naan.  This recipe for the yeast-free Naan breads has become a favorite of mine. No waiting around for yeast to prove, it can be ready to bake in not much longer than half an hour, and only takes about 10 minutes, per bread, to cook, if that.

It is a very simple dough, using very simple ingredients, and I will confess right now, I didn't have any yogurt in the fridge today (How did that happen?  I always have yogurt!) and so I used sour cream instead which I felt would have approximately the same acidity and consistency needed, and as you can see it worked out really well.  

You make the dough and then roll it out to a thin (1/8th inch thick) oval and then you "bake" the ovals on a hot pan/griddle.  First on one side, over medium heat just until you get blisters showing up as you can see below.  It will be light golden on the under side.  This only takes a few minutes.

There is no need to grease the griddle pan/skillet. No oil needed. Once you have blistered them and browned them on the top side, you simply flip them over and toast the other side, again, for only a few minutes.  

They are rather largish, about 6 by 9 inches in size, so you can really only bake/toast one at a time. You will want to wrap the finished ones in a clean tea towel to keep them warm while you finish baking them all. Any that don't get eaten on the day can very easily be frozen to enjoy at a later date.

These are the nicest, softest, most delicious Naan breads you could ever want.  Lovely and fresh. Once you have tried these you will never want to settle for a shop bought Naan again. Actually there is no comparison really . . .  these blow those nasty dry things out of the water! Prepare to fall in love!

 

INGREDIENTS NEEDED

TO MAKE

YEAST-FREE NAAN BREADS

You probably have everything you need to make these in your kitchen/larder right now! 

• 1 1/3 cups (165g) plain all-purpose flour
• 1/2 tsp baking powder
• pinch sugar
• 1/2 tsp salt
• 3 TBS +1 tsp (50ml) whole milk
• 2 TBS butter (cut into bits)
• 1/4 cup (65g) creamy full fat yoghurt

 

NOTES ON INGREDIENTS

• Do not use self raising flour for this recipe.  All-purpose or plain flour is what is needed. 
• It is not a lot of baking powder, but you really don't want a lot. You just want enough to encourage the dough to puff up when it hits the hot griddle pan.
• Just a pinch of sugar. I use Kirkland organic granulated sugar. In the U.K. I would use caster sugar.
• You will want to use whole milk as it has a richer flavor.
• I used salted butter as that is all I keep in my house. I have never found anything to be super-salted in doing so.
• Make sure your yogurt is full fat. Alternately you can use full fat sour cream if you haven't got any yogurt.

 

HOW TO MAKE

YEAST-FREE NAAN BREADS

These are very simple and easy to make. Because there is no yeast involved there is no wait times for them to rise, etc.

1. Sift the flour, baking powder, sugar and salt together.
2. Warm the milk gently with the butter to melt the butter. Cool to lukewarm and whisk in the yogurt. Stir this into the flour mixture with a wooden spoon to make a soft dough. (Keep an eye on the milk. You don't want it to boil, just warm up enough to melt the butter.)
3. If the dough is too sticky, dust lightly with flour. Knead in the bowl for a few minutes, then cover with a clean tea towel and let sit for half an hour.
4. At the end of that time, divide into 4 equal portions and shape into balls. Roll out on a lightly floured surface to 1/8 inch thickness. Rotate slightly as you roll them, sprinkling lightly with flour as you go until you have a rough oval shape. (I find it easy to do this moving them a quarter turn with each roll of the rolling pin.)
5. Heat a large non-stick skillet or flat pancake griddle pan over medium high heat. Once it is hot you can start to bake the Naan's. (You can hold your hand just about the pan and feel how hot it is. I used a Pampered Chef grill pan to cook these on. In most cases you will only be able to cook one at a time.)
6. Pick up and remove any excess flour by slapping the dough between your hands and flip it onto the pan.
7. Cook until the surface is covered with bubbles, and it is lightly toasted on the bottom, flip over and repeat. (Do keep a close watch on it as they can turn very quickly.)
8. Remove to a clean tea-towel and cover to keep warm while you cook the rest. This helps to keep them soft. Serve warm.

 

 

HINTS AND TIPS FOR SUCCESS

• You will want your dough to be not sticky, not dry, but somewhere in the middle.
• Roll your dough out thin so that it cooks out evenly and light.
• Use a well heated non-stick skillet. This will help to create the lovely characteristic bubbles and charring.
• You can vary the flavor by brushing some garlic or herb butter on top of the breads after cooking while they are still warm.
• Keep a close watch on your breads while they are baking. They can turn in the blink of an eye. When they start to blister and puff up, and start turning brown, they are done.
• Keep your Naan breads wrapped loosely in a clean tea towel while you finish cooking them all. This helps to keep them nice and soft and prevents them from drying out.

 

FREQUENTLY ASKED QUESTIONS

CAN THIS BE MADE AHEAD OF TIME?

Yes, make the naan breads, then cool them and place in an airtight container or wrapped in foil. They should be fine at room temperature for 2 days.

HOW CAN I REHEAT THESE?

Reheat them by placing on a baking tray in a single layer, covered in foil. Place in a pre-heated oven at 400*F/200*C for about 5-6 minutes until hot throughout.

CAN THESE BE FROZEN?

Yes, make the naan breads, then cool them and place in an airtight container or wrapped in foil. Label, date and place in the freezer. Defrost overnight in the refrigerator, then reheat as per the make-ahead instructions above. Use within three months.

 

A FEW OTHER SAVORY

QUICK BREADS TO CONSIDER

 A bit of savory bread is always welcome sitting next to soup, curry, stew or a salad.  Here are a few other's that we enjoy that are quick and easy to make!

CHEESE & PEPPER BREAD - This is a wonderfully simple, savory quick bread that comes together in minutes and bakes up into the most gorgeous, golden loaf. It’s rich with sharp cheddar and flecked throughout with coarse black pepper, giving every slice a warm, gently spicy kick that pairs beautifully with the cheese .Made with everyday pantry ingredients, this loaf is stirred together in a flash — no yeast, no kneading, no fuss. Just whisk, mix, bake, and enjoy. Quick breads like this one are perfect when you want something homemade but don’t have hours to spare; they’re stirred together and in the oven lickety‑split!

SIMPLE BRITISH MALT LOAF - A classic, old‑fashioned tea loaf that’s beloved for its sticky texture, deep malty sweetness, and generous amount of dried fruit. It’s the kind of bake you turn to when you want something comforting, wholesome, and wonderfully British — the sort of treat that tastes even better after a day or two of resting. Malt loaf is a sweet quick bread made with malt extract, raisins, prunes, and whole‑grain flours, giving it that signature chewy, dense texture and rich flavor . The fruit is soaked in strong hot tea, which adds even more depth and helps create that lovely squidgy crumb. Once baked, the loaf is sticky, dense, and generously filled with fruit, improving in flavor each day it sits — a true “better‑with‑time” bake

 

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Yield: makes 4 breads

Author: Marie Rayner

Yeast Free Naan Breads

Prep time: 45 MinCook time: 10 MinTotal time: 55 Min

The dough for this can be made ahead and kept in the refrigerator instead of the normal resting time. Just bring back to room temperature before continuing. 

Ingredients

• 1 1/3 cups (165g) plain all-purpose flour
• 1/2 tsp baking powder
• pinch sugar
• 1/2 tsp salt
• 3 TBS +1 tsp (50ml) whole milk
• 2 TBS butter (cut into bits)
• 1/4 cup (65g) creamy full fat yoghurt

Instructions

1. Sift the flour, baking powder, sugar and salt together.
2. Warm the milk gently with the butter to melt the butter. Cool to lukewarm and whisk in the yogurt. Stir this into the flour mixture with a wooden spoon to make a soft dough.
3. If the dough is too sticky, dust lightly with flour. Knead in the bowl for a few minutes, then cover with a clean tea towel and let sit for half an hour.
4. At the end of that time, divide into 4 equal portions and shape into balls. Roll out on a lightly floured surface to 1/8 inch thickness. Rotate slightly as you roll them, sprinkling lightly with flour as you go until you have a rough oval shape.
5. Heat a large non-stick skillet or flat pancake griddle pan over medium high heat. Once it is hot you can start to bake the Naan's.
6. Pick up and remove any excess flour by slapping the dough between your hands and flip it onto the pan.
7. Cook until the surface is covered with bubbles, and it is lightly toasted on the bottom, flip over and repeat.
8. Remove to a clean tea-towel and cover to keep warm while you cook the rest. This helps to keep them soft. Serve warm.

Notes

If you want a garlic flavoured Naan, you can rub the surface of the finished breads with the cut side of a clove of garlic and brush with butter.

Did you make this recipe?

Tag @marierayner5530 on instagram and hashtag it #EnglishKitchen

This content, written and photography, is the sole property of The English Kitchen. Any reposting or misuse is not permitted. If you are reading this elsewhere, please know that it is stolen content and you may report it to me at mariealicejoan at aol dot com.

 

Thanks for visiting! Do come again!! 

 If you like what you see here, why not consider signing up for my newsletter and/or subscribing/following me on Grow. You can also bookmark my recipes via the Grow platform. Check out the heart on the right-hand side of the screen.