10 Old-Fashioned Desserts to Try from Grandma's Recipe Box

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Pineapple Upside-Down Cake

A retro favorite that never goes out of style, pineapple upside-down cake is a buttery, caramelized treat with a moist vanilla cake base. Golden pineapple rings and maraschino cherries are arranged in a rich brown sugar and butter glaze, creating a sweet, sticky topping that makes every slice irresistibly nostalgic. Once flipped out of the pan, the glistening fruit layer steals the show, just like Grandma used to make.

Ingredients (for a 9-inch cake):

• ¼ cup unsalted butter, melted
• ¾ cup brown sugar, packed
• 7 pineapple rings (canned or fresh)
• 7 maraschino cherries
• 1 ½ cups all-purpose flour
• 1 ½ tsp baking powder
• ¼ tsp salt
• ½ cup unsalted butter, softened
• ¾ cup granulated sugar
• 2 large eggs
• 1 tsp vanilla extract
• ½ cup whole milk

Instructions:

1. Preheat oven to 350°F. Pour melted butter into a 9-inch round cake pan, swirling to coat the bottom. Sprinkle brown sugar evenly over the butter. Arrange pineapple rings on top, placing a cherry in the center of each ring.
2. In a bowl, whisk together flour, baking powder, and salt. In a separate bowl, cream butter and granulated sugar until light and fluffy. Beat in eggs, one at a time, then add vanilla.
3. Alternately add flour mixture and milk to the butter mixture, stirring until smooth. Gently spread the batter over the pineapple layer. Bake for 35-40 min., or until a toothpick inserted in the center comes out clean.
4. Let the cake cool for 5-10 min., then carefully invert onto a serving plate. Allow the caramelized fruit to set before slicing.
5. Enjoy warm or at room temperature with a dollop of whipped cream or vanilla ice cream!