Pineapple Upside Down Cake

I think Pineapple Upside Down Cake is the easiest and one of the most delicious cakes to bake. I also think it goes perfect with Thanksgiving! The caramelized glaze that tops the cake keeps the cake so moist – and it looks so beautiful after baking while you didn’t even have to decorate it or frost it – BONUS!

The way I learned to make Pineapple Upside Down Cake was in a cast iron skillet, but if you have a large cake pan I’m pretty sure it will work in that as well.



1/4    cup butter or margarine
2/3    cup packed brown sugar
9  (or however many will fit into your cake pan attractively)  slices pineapple in juice (from 14-oz can), drained
9 or so maraschino cherries without stems, if desired
1 1/3    cups  all-purpose flour
1  cup granulated sugar
1/3    cup shortening
1 1/2    teaspoons baking powder
1/2    teaspoon salt
3/4    cup milk
1    egg
Heat oven to 350°F. In a large skillet or cake pan, melt butter in oven. Sprinkle brown sugar evenly over melted butter. Arrange pineapple slices over brown sugar. Place cherry in center of each pineapple slice.


In medium bowl, beat remaining ingredients with electric mixer on low speed 30 seconds, scraping bowl constantly. Beat on high speed 3 minutes, scraping bowl occasionally. Pour batter over pineapple and cherries.


Bake 50 to 55 minutes or until toothpick inserted in center comes out clean. Cool cake in pan on a rack for 10 minutes. Turn cake out onto a platter. Serve warm or at room temperature.  Store cake loosely covered.


When my mom makes this cake she sometimes adds crushed pecans or walnuts to the butter and brown sugar mixture.  She has also made this with sliced peaches instead of pineapple rings – and wow that’s delicious too! In fact you could probably top this cake with whatever fruit or berries is your favorite and it would taste fantastic!