#12TastesofChristmas – Pineapple Upside Down Cake

On the fifth day of Christmas my true love gave to me…five golden rings,
Four calling birds,
Three French hens,
Two turtle doves,
And a partridge in a pear tree.

Pineapple Upside Down Cake

This one was an absolute no brainer. Golden rings? Pineapple. I suppose onion rings or squash rings or other things like that would also work, but they don’t strike me as very Christmas-y while pineapple upside down cake is a tradition in my family. It goes back at least as far as my grandmother as a young woman, who would bake it for holidays for her children.
And it just makes such a beautiful addition to the table, doesn’t it? The buttery cake, the caramelization, the contrast with the bright red cherries. It’s lovely.


1/4 cup butter
1/2 cup light brown sugar
Canned pineapple slices (reserve juice for cake)
15-20 maraschino cherries

1 and 2/3 cups all-purpose flour
1/2 teaspoon baking powder
1/4 teaspoon baking soda
1/2 teaspoon salt
1/2 cup butter, melted
3/4 cup light brown sugar
1/4 cup granulated sugar
1 large egg
1/4 cup yogurt
1/2 cup milk
1/4 cup pineapple juice
1 tablespoon vanilla extract


Heat oven to 350°F (325°F for dark or nonstick pan). You’ll prepare the topping first. In 13×9-inch pan, melt butter in oven. Sprinkle brown sugar evenly over butter. Arrange pineapple slices on brown sugar. Place cherry in center of each pineapple slice, and arrange remaining cherries around slices; press gently into brown sugar.
Now the cake. Mix flour, baking powder, baking soda, and salt and set aside. Melt butter in the microwave and then whisk into the sugars. To the wet mix, beat in egg, yogurt, milk, pineapple juice, and vanilla extract. Slowly sift in the dry ingredients until no lumps remain. This will be a thick, rich batter that’s difficult to mix by hand by the time you’re done.
Pour the batter over the pineapple and cherries. Bake 42 to 48 minutes (44 to 53 for dark or nonstick pans) or until a toothpick inserted in the center comes out clean. Immediately run a knife around the sides of the pan to loosen the cake, then put a heatproof serving plate upside down onto the pan. Turn the plate and pan over together and leave like this for five minutes so the caramelized brown sugar can drizzle all over the cake.
Once that’s done, remove the pan and let the cake continue to cool for 30 minutes. Eat until you feel like you’re going to puke pineapple.

2 thoughts on “#12TastesofChristmas – Pineapple Upside Down Cake

  1. Pingback: #12TastesofChristmas – Eggless Eggnog | C.M. Stone

  2. Pingback: #12TastesofChristmas – Swimming Swan Sandwiches | C.M. Stone

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