Gingerbread Pineapple Upside Down Cake

I was away for the weekend at Baltimore Yearly Meeting’s annual Women’s Retreat. It was a blast! While I was away, Don made us a lovely dessert for Sunday supper: Gingerbread Pineapple Upside Down Cake! Using gingerbread instead of the traditional yellow cake makes it very flavorful. We’d like to take credit for coming up with this idea, but we can’t.

Some years ago Don and I were at a dinner party in Williamsburg, Virginia, and pineapple upside down cake was served for dessert. Lucy Grubb, one of the older guests, told of how her mother would make Pineapple Upside Down Cake with gingerbread instead of the traditional yellow cake. We tried it and have been hooked ever since. The gingerbread version is great comfort food for Don in the wintertime, but it’s a bit too heavy for the hot days of summer.

Don makes it the traditional way, in a 10-inch cast iron skillet. To serve, upend the skillet onto a serving platter. Some for the pineapple rings may stay behind, but they are easily lifted from the skillet and placed back on the top of the gingerbread (which, of course, used to be the bottom of the cake until you turn it over).

Gingerbread Pineapple Upside Down Cake is full of flavor and perfect for a cold winter's day.


The topping
(which is baked on the bottom)

 4 tablespoons of butter
¾ cup of brown sugar
7 rings of canned pineapple
About a dozen or so maraschino cherry halves

Heat the butter in the skillet until it melts. Swirl the skillet to coat part way up the sides. Cover the bottom of the skillet with the brown sugar. Place the pineapple rings over the brown sugar around the edge and one in the center of the skillet. Place a maraschino cherry half in the center of each pineapple ring (all with the round side down) and add more in between the rings if you want.

 The Gingerbread

 Preheat the oven to 350 F degrees. 

½ cup of butter, softened
½ cup of sugar
2 eggs, beaten
1 cup molasses
1 teaspoon cinnamon
2 teaspoons baking soda
½ teaspoon ground cloves
½ teaspoon ground ginger
2 ½ cups flour
1 cup boiling water

Cream the butter and sugar. Mix in the eggs and molasses. In a separate bowl mix the remaining dry ingredients then fold into the liquid mixture. Add the boiling water, mix well and pour it over top of the pineapple rings.

 Bake for 40-45 minutes or until a toothpick inserted near the center comes out clean.

Remove the skillet from the oven and let it rest for a minute, no longer. (You may find it helpful to loosen the cake from the outside edge of the pan before you do the next step.)Place the serving platter over the skillet and turn it upside down to reveal the dark brown gingerbread topped with pineapple rings and cherries. Let cool and serve just how it is or add whipped cream for elegance.


About Lois

My husband, Don Crawford, and I love to cook. For me, it's more about eating delicious food than the actual cooking. I like to cook mostly because I like to eat, and I like the proud sense of accomplishment when the food I make is appreciated by others. For Don, it's all about presentation. So we make a good team. I'm too impatient to create beautiful presentations (usually), but he sweeps in and takes over so it all turns out great. All our recipes are tried and true!
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3 Responses to Gingerbread Pineapple Upside Down Cake

  1. Don says:

    I finished the last piece of the Pineapple Upside Down Cake last night. It’s a good cake to enjoy over a week’s time because it is heavy and moist it keeps well covered on the counter where it is within easy reach ;-). Next time I’ll add some chopped walnuts in the topping and reduce the brown sugar by a third to see what difference that makes.
    It’s Lois’ turn to cook this weekend. I can’t wait to see what she prepares!

  2. nancygerst says:

    Hello Lois, I made this recipe yesterday and we both loved it! I think my Dad would especially enjoy it too, so I’ll make one to take with us for our next visit to IN. I didn’t have pineapple rings, so I used crushed pineapple and used the juice in place of the water. Thanks for publishing this delicious blog. We’ve enjoyed several of the recipes. Nancy next door

    • Lois says:

      Thanks, Nancy. What a good idea to use the juice instead of water. I will have to try it. I hope your dad loves it, too.

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