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Grandmother's Pineapple Upside-Down Cake Recipe

My grandmother made this cake for special occasions and for Sundays after church. It was the only cake her son would eat.

My grandmother's pineapple upside-down cake

My grandmother's pineapple upside-down cake

My Uncle's Favorite Cake

During World War II, my grandmother made her pineapple upside-down cake in honor of her only son, who was a POW. Before the war, this cake was the only one he would eat.

She traditionally made this cake for after church dinners on Sundays and it was kept in her icebox. Every recipe in her recipe book was dated, and this recipe is dated 1943.

I remember the wonderful cakes my grandmother used to make and serve on her veranda surrounded by her beautiful roses and flowers.

Cook Time

Prep timeCook timeReady inYields

35 min

40 min

1 hour 15 min

8 to 10 servings


  • 1/3 cup butter
  • 1 cup granulated sugar
  • 1 egg, well beaten
  • 1 3/4 cups flour
  • 3 teaspoons baking powder
  • 6 or more slices canned pineapple
  • 1/4 teaspoon salt
  • 1 teaspoon orange extract
  • 1/2 cup milk
  • 3 tablespoons butter
  • 1/4 cup brown sugar
  • 8 to 10 or more maraschino cherries, stems removed


  1. Cream the butter and sugars together. Add the egg and flavoring.
  2. Sift together the dry ingredients and add to the first mixture alternately with the milk.
  3. Rub the bottom and sides of a heavy iron frying pan with butter.
  4. Place slices of pineapple on the bottom and sides of pan.
  5. Place cherries in the middle of pineapple rings on the bottom.
  6. Pour the cake mixture over the pineapple and cherries.
  7. Bake in a moderate oven at 375 degrees for about 40 minutes. Check for doneness.
  8. Turn out the cake onto a round cake dish. Grandmother served the cake hot. She added her whipped cream freshly made or ice cream churned that morning.
Me with my Uncle Brice on my grandparents' farm. Uncle Brice was a POW during WWII. This pineapple upside-down cake was his favorite.

Me with my Uncle Brice on my grandparents' farm. Uncle Brice was a POW during WWII. This pineapple upside-down cake was his favorite.

Grandmother Taught Me How to Bake

When I was only three my grandmother made a small apron for me to wear when I helped her bake. She stood me on a stool at her baking table. She taught me how to measure with and without a measuring cup.

This cake was for special occasions and for Sundays after church. Grandmother put most cakes in her safe (a screened-in cabinet with screened doors.) This was used for a temporary place for her cakes and pies that did not need to be on ice.

An iceman would come once or twice a week to replenish the icebox on our country farm. I barely remember the icebox.

Then, electricity came to the area and my grandmother got a refrigerator, as well as a new bathroom with shower and tub. It seemed to all happen at once.

I know it was easier on the family, and especially my grandmother, who never complained. Yes, she was a country angel to so many people. I will never be as good a person as she was during her earthly time with our family.

The way I see it, God made grandmothers just for the sweet little grandchildren to love and spend time with on the farm. I remember summertime being the most special time with our grandmother. She taught us so many things to enrich our lives, even to this day.

Personal note: My sister, Paula, has Grandmother Knight's "safe" in her home—and it is a most cherished piece of furniture. Whenever we have a family get-together, we all visit the safe just to touch it.

© 2022 Barbara Purvis Hunter