Some recipes carry a story in every bite. This pineapple upside-down cake is one of them — a beloved family classic that has shown up at birthdays, Sunday suppers, and every celebration in between for as long as I can remember.
Growing up in Frankfort, Kentucky, our kitchen was always full of the kind of cooking that brought people together. Every year on my birthday, this cake made an appearance — golden caramelized pineapple, a buttery cake, and those cherries on top that made it look almost too pretty to eat. Almost.
Over the years I’ve made it my own with one very curious twist: swapping out the maraschino cherries for our Boozy Cherries® — bourbon-soaked cocktail cherries that add a rich, grown-up depth that takes this nostalgic dessert somewhere truly special. It’s the same cake, just a little more curious.
I hope it becomes a tradition in your kitchen too.
🍒 The Secret Ingredient
The one thing that takes this cake from classic to curious? Our Boozy Cherries® bourbon-soaked cocktail cherries bring a rich, grown-up depth to every bite. Swap them in for maraschino, and you’ll never go back.
INGREDIENTS
1/4 cup butter
2/3 cup packed brown sugar
9 slices pineapple in juice (from 20 oz. can), drained
9 maraschino cherries (substitute with Boozy Cherries® if desired)
1 and 1/3 cup all-purpose flour
1 cup granulated sugar
1/3 cup shortening
1 and 1/2 teaspoons baking powder
1/2 teaspoon Kosher salt
3/4 cup whole milk
1 large egg
DIRECTIONS
- Heat oven to 350° F. In a 9-inch square pan (I used my cast iron skillet), melt butter. Once butter has melted, sprinkle brown sugar into pan and stir until combined. Arrange pineapple slices over the brown sugar mixture. Place maraschino or Boozy Cherries® in center of each pineapple slice.
- In a medium bowl, add flour, sugar, shortening, baking powder, Kosher salt, milk, and egg. Beat ingredients with an electric mixer (I used my hand mixer for ease of clean up) for 30 seconds on low, scraping bowl constantly. Beat on high for an additional 2 minutes, scraping bowl occasionally. Pour batter over pineapple and cherries.
- Bake for 45 to 55 minutes or until toothpick comes out clean. I checked my cake at 45 minutes and it was fully baked, I always test a few minutes early just in case my oven is running hot. Immediately place heatproof serving plate upside down over pan or skillet; turn plate and pan over. Leave pan/skillet over cake to allow brown sugar mixture to drizzle over cake; carefully remove pan/skillet. Serve warm. Store cake loosely covered.
